# EDGAR Filing Document

**Accession Number:** 0000864230
**File Stem:** 0001580642-23-000111
**Filing Date:** 2023-1
**Character Count:** 91654
**Document Hash:** b3373e6cfcfe50f59f35c680b155e3a2
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001580642-23-000111.hdr.sgml**: 20230109

**ACCESSION NUMBER**: 0001580642-23-000111

**CONFORMED SUBMISSION TYPE**: N-CSRS

**PUBLIC DOCUMENT COUNT**: 5

**CONFORMED PERIOD OF REPORT**: 20221031

**FILED AS OF DATE**: 20230109

**DATE AS OF CHANGE**: 20230109

**EFFECTIVENESS DATE**: 20230109

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** CALDWELL & ORKIN FUNDS INC
- **CENTRAL INDEX KEY:** 0000864230
- **IRS NUMBER:** 581895283
- **STATE OF INCORPORATION:** MD
- **FISCAL YEAR END:** 0430

**FILING VALUES:**
- **FORM TYPE:** N-CSRS
- **SEC ACT:** 1940 Act
- **SEC FILE NUMBER:** 811-06113
- **FILM NUMBER:** 23517244

**BUSINESS ADDRESS:**
- **STREET 1:** 100 S. ASHLEY DRIVE
- **STREET 2:** SUITE 895
- **CITY:** TAMPA
- **STATE:** FL
- **ZIP:** 33602
- **BUSINESS PHONE:** 813-282-7870

**MAIL ADDRESS:**
- **STREET 1:** 100 S. ASHLEY DRIVE
- **STREET 2:** SUITE 895
- **CITY:** TAMPA
- **STATE:** FL
- **ZIP:** 33602

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** OTC SELECT 100 FUND INC
- **DATE OF NAME CHANGE:** 19920629

## Series and Classes Contracts Data

### Caldwell & Orkin - Gator Capital Long/Short Fund (Series ID: S000011446)

| Class ID   | Class Name                                       | Ticker Symbol   |
|:---|:---|:---|
| C000031655 | Caldwell & Orkin - Gator Capital Long/Short Fund | COAGX           |

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

**FORM N-CSRS**

**CERTIFIED SHAREHOLDER REPORT OF REGISTERED**

**MANAGEMENT INVESTMENT COMPANIES**

Investment Company Act file number : <u>811-06113</u>

**<u>The Caldwell & Orkin Funds, Inc.</u>**

(Exact name of registrant as specified in charter)

100 S. Ashley Drive, Suite 895

<u>Tampa, Florida 33602</u>

(Address of principal executive offices) (Zip code)

Derek Pilecki

100 S. Ashley Drive, Suite 895

<u>Tampa, Florida 33602</u>

(Name and address of agent for service)

*Copies to:*

Jesse Halle

Ultimus Fund Solutions, LLC

225 Pictoria Drive, Suite 450

Cincinnati, OH 45246

Registrant's telephone number, including area code: <u>1-813-282-7870</u>

Date of fiscal year end: <u>April 30</u>

Date of reporting period: <u>October 31, 2022</u>

**Item 1. Reports to Stockholders.**

&nbsp;&nbsp;&nbsp;&nbsp;(a) ![(COVER PAGE)](co001_v1.jpg)

Caldwell & Orkin - <br> <u>**Table of Contents**</u> <u>Gator Capital Long/Short Fund</u> <br> *October 31, 2022 (Unaudited)*

---

| | |
|:---|:---|
| Management's Discussion of Fund Performance | 2 |
| Investment Results | 4 |
| Fund Holdings | 5 |
| Schedule of Investments | 6 |
| Schedule of Securities Sold Short | 10 |
| Statement of Assets and Liabilities | 12 |
| Statement of Operations | 13 |
| Statements of Changes in Net Assets | 14 |
| Financial Highlights | 15 |
| Notes to Financial Statements | 16 |
| Disclosure of Fund Expenses | 23 |
| Director Approval of the Investment Advisory Agreement | 24 |
| Privacy Policy Disclosure | 26 |

---

Caldwell & Orkin - Management's Discussion <br> <u>Gator Capital Long/Short Fund</u> <u>of Fund Performance</u> <br> *October 31, 2022 (Unaudited)*

November 29, 2022

**Dear Fellow Shareholder:**

The Caldwell & Orkin – Gator Capital Long/Short Fund (the "Fund") declined 4.71% over the six-month period ending on October 31, 2022. The S&P 500<sup>®</sup> Total Return Index ("S&P 500<sup>®</sup>") declined 5.50% during the same period. For the 12-month period ending October 31, 2022, the Fund declined 5.77% while the S&P 500<sup>®</sup> declined 14.61%.

*Past performance is no guarantee of future results.*

**Management Discussion and Analysis**

The Fund outperformed the S&P 500<sup>®</sup> during the first half of fiscal year 2023. The Fund's long exposure to Financial stocks and short exposure to Real Estate stocks were the main drivers of performance.

The top five equity contributors during the first half of fiscal year 2023 were Genworth Financial, Inc. (long), First BanCorp (long), Boston Properties, Inc. (short), Vornado Realty Trust (short), and Compass, Inc. (short).

The top five equity detractors during the first half of fiscal year 2023 were Ally Financial, Inc. (long), Anywhere Real Estate, Inc. (long), Meta Platforms, Inc. (long), United States Steel Corp. (long), and Audacy, Inc. (long).

We ended the first half of the 2023 fiscal year with gross long exposure of 94% and gross short exposure of 36% for a total gross exposure of 131% and a net exposure of 58%.

**Opportunities in Small Banks**

We continue to see opportunities in small banks. These banks trade at compelling valuations, and we believe earnings will grow. They will earn higher net interest margins from higher interest rates, and they are seeing significant loan growth. Unlike other investors, we do not anticipate significant credit losses from bad loans for these banks. We believe these banks have strong credit underwriting and we are more bullish on the economy than the average investor. We believe the combination of low valuations, attractive earnings growth due to higher rates, and loan growth is a winning formula for our small bank holdings.

**Conclusion**

Thank you for entrusting us with a portion of your wealth. We are grateful for investors like you who believe and trust in our strategy. As always, we welcome the opportunity to speak with you and discuss the Fund.

Sincerely,

Derek S. Pilecki, CFA

Portfolio Manager

2 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - Management's Discussion <br> <u>Gator Capital Long/Short Fund</u> <u>of Fund Performance</u> <br> *October 31, 2022 (Unaudited)*

The discussion of individual companies should not be considered a recommendation of such companies by the Fund's investment adviser.

**The performance data quoted represents past performance. Past performance is no guarantee of future results. The investment returns and principal value of an investment in the Fund will fluctuate so that an investor's shares, when redeemed, may be worth more or less than their original cost. Current performance may be higher or lower than the performance data quoted.** Please call 800-467-7903 or visit <u>www.CaldwellOrkin.com</u> for current month-end performance.

The Fund is distributed by Ultimus Fund Distributors, LLC, member FINRA/SIPC.

Current and future portfolio holdings are subject to change and risk.

**Investors should consider the investment objective, risks, and charges and expenses of the Fund before investing. The prospectus and the summary prospectus contain this and other information about the Fund and should be read carefully before investing. The prospectus may be obtained by calling 800-467-7903 or by visiting <u>www.CaldwellOrkin.com</u>.**

Semi-Annual Report \| October 31, 2022 3

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Investment Results</u> <br> *October 31, 2022 (Unaudited)*

---

| | | | | | |
|:---|:---|:---|:---|:---|:---|
| **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** | **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** | **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** | **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** | **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** | **Average Annual Total Returns<sup>(a)</sup> as of October 31, 2022** |
|  | **Six Months** | **One Year** | **Three Year** | **Five Year** | **Ten Year** |
| Caldwell & Orkin - Gator Capital Long/Short Fund | (4.71)% | (5.77)% | 10.64% | 6.34% | 3.46% |
| S&P 500<sup>®</sup> Total Return Index(<sup>b)</sup> | (5.50)% | (14.61)% | 10.22% | 10.44% | 12.79% |
| Eurekahedge Long Short Equities Hedge Fund Index<sup>(c)</sup> | (4.31)% | (10.25)% | 6.73% | 5.09% | 6.80% |
| Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. | Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. | Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. | Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. | Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. | Total annualized Fund operating expenses for the Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund") was 3.09% as described in the Prospectus, dated August 26, 2022. This amount includes Acquired Fund Fees and Expenses, as well as interest and dividend expenses related to short sales, which if excluded would result in an annual operating expense rate of 2.00%. Additional information about the Fund's current fees and expenses for the six months ended October 31, 2022 is contained in the Financial Highlights. |

---

*<sup>(a)</sup>* *Return figures reflect any change in price per share and assume the reinvestment of all distributions. The Fund's returns reflect any fee reductions during the applicable period. If such fee reductions had not occurred, the quoted performance would have been lower. The table does not reflect the deduction of taxes. The Fund's returns represent past performance and do not guarantee future results. The Fund's returns represent past performance and do not guarantee future results.*

 

*<sup>(b)</sup>* *The S&P 500<sup>®</sup> Total Return Index is a capitalization-weighted, unmanaged index of 500 large U.S. companies chosen for market capitalization, liquidity and industry group representation and includes reinvested dividends. You cannot invest directly in an index.*

*<sup>(c)</sup>* *The Eurekahedge Long Short Equities Hedge Fund Index ("Eurekahedge Index") is an unmanaged index comprised of long/short equity hedge funds. According to its sponsor, Eurekahedge Pte. Ltd., the Eurekahedge Index is an equally weighted index of 895 constituent funds designed to provide a broad measure of the performance of underlying hedge fund managers. The returns of the Eurekahedge Index do not include sales charges or fees, which would lower performance. You cannot invest directly in an index.*

***You should consider the Fund's investment objectives, risks, charges and expenses carefully before you invest. The Fund's prospectus contains important information about the Fund's investment objectives, potential risks, management fees, charges and expenses, and other information and should be read carefully before investing. You may obtain a current copy of the Fund's prospectus or performance data current to the most recent month by calling (800) 467-7903.***

***The Fund is distributed by Ultimus Fund Distributors, LLC, member FINRA/SIPC.***

4 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Fund Holdings</u> <br> *October 31, 2022 (Unaudited)*

---

| |
|:---|
| **Net Sector Exposure** |
| **October 31, 2022\*** |

---

![(BAR CHART)](co002_v1.jpg)

\* *Sector weightings are calculated as a percentage of net assets and include short positions. Portfolio holdings are subject to change.*

The Caldwell & Orkin - Gator Capital Long/Short Fund's (the "Fund") investment objective is to provide long-term capital growth with a short-term focus on capital preservation.

**<u>Availability of Portfolio Schedule – (Unaudited)</u>**

The Fund files its complete schedule of portfolio holdings with the Securities and Exchange Commission (the "SEC") for the first and third quarters of each fiscal year as an exhibit to its reports on Form N-PORT, within sixty days after the end of the period. The Fund's Form N-PORT reports are available at the SEC's website at www.sec.gov and on the Fund's website at www.gatorcapital.com.

Semi-Annual Report \| October 31, 2022 5

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **COMMON STOCKS — LONG — 93.31%** |  |  |
| &nbsp;&nbsp;&nbsp;**Banks — 35.34%** |  |  |
| &nbsp;&nbsp;&nbsp;Axos Financial, Inc.<sup>(a)</sup> | 5900 | $229864 |
| &nbsp;&nbsp;&nbsp;Bridgewater Bancshares, Inc.<sup>(a)</sup> | 24000 | 458880 |
| &nbsp;&nbsp;&nbsp;Citizens Financial Group, Inc. | 10000 | 409000 |
| &nbsp;&nbsp;&nbsp;ConnectOne Bancorp, Inc. | 9400 | 235470 |
| &nbsp;&nbsp;&nbsp;Dime Community Bancshares, Inc. | 7063 | 243885 |
| &nbsp;&nbsp;&nbsp;Financial Institutions, Inc. | 4520 | 107712 |
| &nbsp;&nbsp;&nbsp;First BanCorp. | 62800 | 991612 |
| &nbsp;&nbsp;&nbsp;First Business Financial Services, Inc. | 7500 | 286125 |
| &nbsp;&nbsp;&nbsp;First Citizens BancShares, Inc., Class A | 471 | 387219 |
| &nbsp;&nbsp;&nbsp;First Internet Bancorp | 10000 | 256900 |
| &nbsp;&nbsp;&nbsp;Meridian Bancorp, Inc. | 6344 | 195332 |
| &nbsp;&nbsp;&nbsp;OFG Bancorp | 24700 | 688636 |
| &nbsp;&nbsp;&nbsp;PacWest BanCorp | 20300 | 504658 |
| &nbsp;&nbsp;&nbsp;Popular, Inc. | 7000 | 495040 |
| &nbsp;&nbsp;&nbsp;Republic First Bancorp, Inc.<sup>(a)</sup> | 52716 | 149186 |
| &nbsp;&nbsp;&nbsp;Webster Financial Corp. | 11000 | 596860 |
| &nbsp;&nbsp;&nbsp;Western Alliance Bancorp | 7100 | 476907 |
|  |  | 6713286 |
| &nbsp;&nbsp;&nbsp;**Casinos & Gaming — 1.55%** |  |  |
| &nbsp;&nbsp;&nbsp;Las Vegas Sands Corp.<sup>(a)</sup> | 6000 | 228060 |
| &nbsp;&nbsp;&nbsp;Melco Resorts & Entertainment Ltd. - ADR<sup>(a)</sup> | 12000 | 65640 |
|  |  | 293700 |
| &nbsp;&nbsp;&nbsp;**Coal Mining — 1.68%** |  |  |
| &nbsp;&nbsp;&nbsp;SunCoke Energy, Inc. | 44000 | 319440 |
| &nbsp;&nbsp;&nbsp;**Computer Hardware & Storage — 1.71%** |  |  |
| &nbsp;&nbsp;&nbsp;Dell Technologies, Inc., Class C | 4000 | 153600 |
| &nbsp;&nbsp;&nbsp;Hewlett Packard Enterprise Co. | 12000 | 171240 |
|  |  | 324840 |
| &nbsp;&nbsp;&nbsp;**Consumer Finance — 10.34%** |  |  |
| &nbsp;&nbsp;&nbsp;Navient Corp. | 42063 | 636834 |
| &nbsp;&nbsp;&nbsp;OneMain Holdings, Inc. | 12500 | 482000 |
| &nbsp;&nbsp;&nbsp;SLM Corp. | 24000 | 398160 |
| &nbsp;&nbsp;&nbsp;Synchrony Financial | 12600 | 448056 |
|  |  | 1965050 |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> 6 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
| | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Data & Transaction Processors — 2.07%** |  |  |
| &nbsp;&nbsp;&nbsp;Visa, Inc., Class A | 1900 | $393604 |
| &nbsp;&nbsp;&nbsp;**Diversified Banks — 2.64%** |  |  |
| &nbsp;&nbsp;&nbsp;Barclays PLC, Sponsored - ADR | 72500 | 501700 |
| &nbsp;&nbsp;&nbsp;**Film & TV — 1.81%** |  |  |
| &nbsp;&nbsp;&nbsp;Warner Bros. Discovery, Inc.<sup>(a)</sup> | 26500 | 344500 |
| &nbsp;&nbsp;&nbsp;**Health Care Supplies — 0.05%** |  |  |
| &nbsp;&nbsp;&nbsp;Neogen Corp.<sup>(a)</sup> | 670 | 8844 |
| &nbsp;&nbsp;&nbsp;**Hotel REITs — 1.86%** |  |  |
| &nbsp;&nbsp;&nbsp;Park Hotels & Resorts, Inc. | 27000 | 353160 |
| &nbsp;&nbsp;&nbsp;**Infrastructure Software — 1.05%** |  |  |
| &nbsp;&nbsp;&nbsp;VMware, Inc., Class A | 1762 | 198278 |
| &nbsp;&nbsp;&nbsp;**Insurance Brokers & Services — 0.25%** |  |  |
| &nbsp;&nbsp;&nbsp;Kingstone Companies, Inc. | 22629 | 47973 |
| &nbsp;&nbsp;&nbsp;**Internet Media & Services — 0.99%** |  |  |
| &nbsp;&nbsp;&nbsp;Meta Platforms, Inc., Class A<sup>(a)</sup> | 2000 | 186320 |
| &nbsp;&nbsp;&nbsp;**Investment Companies — 2.67%** |  |  |
| &nbsp;&nbsp;&nbsp;BBX Capital, Inc.<sup>(a)</sup> | 69638 | 506268 |
| &nbsp;&nbsp;&nbsp;**Life Insurance — 9.41%** |  |  |
| &nbsp;&nbsp;&nbsp;Genworth Financial, Inc., Class A<sup>(a)</sup> | 184500 | 861615 |
| &nbsp;&nbsp;&nbsp;Jackson Financial, Inc., Class A | 24100 | 924476 |
|  |  | 1786091 |
| &nbsp;&nbsp;&nbsp;**Local TV & Radio Broadcast — 0.12%** |  |  |
| &nbsp;&nbsp;&nbsp;Audacy, Inc.<sup>(a)</sup> | 68000 | 23501 |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> Semi-Annual Report \| October 31, 2022 7

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
| | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Mortgage Finance — 2.53%** |  |  |
| &nbsp;&nbsp;&nbsp;PennyMac Financial Services, Inc. | 9000 | $479880 |
| &nbsp;&nbsp;&nbsp;**P&C Insurance — 4.73%** |  |  |
| &nbsp;&nbsp;&nbsp;Ambac Financial Group, Inc.<sup>(a)</sup> | 18700 | 262735 |
| &nbsp;&nbsp;&nbsp;NMI Holdings, Inc., Class A<sup>(a)</sup> | 29000 | 635970 |
|  |  | 898705 |
| &nbsp;&nbsp;&nbsp;**Private Equity — 3.43%** |  |  |
| &nbsp;&nbsp;&nbsp;Victory Capital Holdings, Inc., Class A | 22500 | 650700 |
| &nbsp;&nbsp;&nbsp;**Real Estate Services — 1.76%** |  |  |
| &nbsp;&nbsp;&nbsp;Anywhere Real Estate, Inc.<sup>(a)</sup> | 45000 | 334350 |
| &nbsp;&nbsp;&nbsp;**Steel Producers — 1.82%** |  |  |
| &nbsp;&nbsp;&nbsp;United States Steel Corp. | 17000 | 346120 |
| &nbsp;&nbsp;&nbsp;**Wealth Management — 5.50%** |  |  |
| &nbsp;&nbsp;&nbsp;Ameriprise Financial, Inc. | 2500 | 772799 |
| &nbsp;&nbsp;&nbsp;Virtus Investment Partners, Inc. | 1600 | 274384 |
|  |  | 1047183 |
| &nbsp;&nbsp;&nbsp;**TOTAL COMMON STOCKS — LONG—** |  |  |
| &nbsp;&nbsp;&nbsp;**(Cost $15,452,815)** |  | 17723493 |
| &nbsp;&nbsp;&nbsp;**PREFERRED STOCKS — LONG — 0.52%** |  |  |
| &nbsp;&nbsp;&nbsp;**Specialty Finance — 0.52%** |  |  |
| &nbsp;&nbsp;&nbsp;Federal National Mortgage Association<sup>(a)</sup> | 9625 | 47644 |
| &nbsp;&nbsp;&nbsp;Federal National Mortgage Association, Series R, 7.63%<sup>(a)</sup> | 20250 | 51435 |
|  |  | 99079 |
| &nbsp;&nbsp;&nbsp;**TOTAL PREFERRED STOCKS — LONG —** |  |  |
| &nbsp;&nbsp;&nbsp;**(Cost $176,270)** |  | 99079 |
| &nbsp;&nbsp;&nbsp;**WARRANTS — LONG — 0.10%** |  |  |
| &nbsp;&nbsp;&nbsp;Ampco-Pittsburgh Corp., Expires 08/01/25, Strike Price $6 | 91000 | 19328 |
| &nbsp;&nbsp;&nbsp;**TOTAL WARRANTS — LONG —** |  |  |
| &nbsp;&nbsp;&nbsp;**(Cost $27,297)** |  | 19328 |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> 8 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
| | **Shares** | **Fair Value** |
| **MONEY MARKET FUNDS — 5.73%** |  |  |
| First American Treasury Obligations Fund - Class X, 3.06%<sup>(b)</sup> | 1088792 | $1088792 |
| **TOTAL MONEY MARKET FUNDS** |  |  |
| **(Cost $1,088,792)** |  | 1088792 |
| **TOTAL INVESTMENTS — 99.66%** |  |  |
| **(Cost $16,745,174)** |  | 18930692 |
| **Other Assets in Excess of Liabilities — 0.34%** |  | 65531 |
| **NET ASSETS — 100.00%** |  | $18996223 |

---

 

*<sup>(a)</sup>* *Non-income producing security.*

*<sup>(b)</sup>* *Rate disclosed is the seven day effective yield as of October 31, 2022.* 

ADR - American Depositary Receipt

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> Semi-Annual Report \| October 31, 2022 9

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Securities Sold Short</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **COMMON STOCKS — SHORT — (35.22)%** |  |  |
| &nbsp;&nbsp;&nbsp;**Applications Software — (0.05)%** |  |  |
| &nbsp;&nbsp;&nbsp;Root, Inc.<sup>(a)</sup> | (1055) | $(8999) |
| &nbsp;&nbsp;&nbsp;**Automobiles — (0.29)%** |  |  |
| &nbsp;&nbsp;&nbsp;Tesla, Inc.<sup>(a)</sup> | (240) | (54610) |
| &nbsp;&nbsp;&nbsp;**Banks — (24.23)%** |  |  |
| &nbsp;&nbsp;&nbsp;Bank of Hawaii Corp. | (3600) | (273420) |
| &nbsp;&nbsp;&nbsp;BankUnited, Inc. | (7000) | (251650) |
| &nbsp;&nbsp;&nbsp;Capitol Federal Financial, Inc. | (27000) | (220860) |
| &nbsp;&nbsp;&nbsp;City Holding Co. | (2301) | (232056) |
| &nbsp;&nbsp;&nbsp;Commerce Bancshares, Inc. | (4305) | (304966) |
| &nbsp;&nbsp;&nbsp;Community Bank System, Inc. | (2700) | (168561) |
| &nbsp;&nbsp;&nbsp;First Financial Bankshares, Inc. | (6250) | (240563) |
| &nbsp;&nbsp;&nbsp;Flushing Financial Corp. | (3960) | (78012) |
| &nbsp;&nbsp;&nbsp;Northwest Bancshares, Inc. | (9142) | (137679) |
| &nbsp;&nbsp;&nbsp;Park National Corp. | (1700) | (250750) |
| &nbsp;&nbsp;&nbsp;Renasant Corp. | (11800) | (476366) |
| &nbsp;&nbsp;&nbsp;Seacoast Banking Corporation of Florida | (8500) | (262650) |
| &nbsp;&nbsp;&nbsp;Simmons First National Corp., Class A | (13700) | (327019) |
| &nbsp;&nbsp;&nbsp;Stock Yards Bancorp, Inc. | (3200) | (250208) |
| &nbsp;&nbsp;&nbsp;Trustmark Corp. | (10000) | (365700) |
| &nbsp;&nbsp;&nbsp;United Bankshares, Inc. | (15100) | (639485) |
| &nbsp;&nbsp;&nbsp;Westamerica Bancorp | (1951) | (122386) |
|  |  | (4602331) |
| &nbsp;&nbsp;&nbsp;**Catalog & TV Based Retailers — (0.42)%** |  |  |
| &nbsp;&nbsp;&nbsp;Warby Parker, Inc., Class A<sup>(a)</sup> | (5000) | (80250) |
| &nbsp;&nbsp;&nbsp;**Commercial Vehicles — (0.20)%** |  |  |
| &nbsp;&nbsp;&nbsp;Nikola Corp.<sup>(a)</sup> | (10000) | (37900) |
| &nbsp;&nbsp;&nbsp;**Industrial Wholesale & Rental — (2.13)%** |  |  |
| &nbsp;&nbsp;&nbsp;SiteOne Landscape Supply, Inc.<sup>(a)</sup> | (3500) | (405545) |
| &nbsp;&nbsp;&nbsp;**Infrastructure Software — (0.10)%** |  |  |
| &nbsp;&nbsp;&nbsp;Upstart Holdings, Inc.<sup>(a)</sup> | (800) | (18544) |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> 10 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Schedule of Securities Sold Short</u> <br> *October 31, 2022 (Unaudited)*

---

| | | |
|:---|:---|:---|
| | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Internet Media & Services — (0.10)%** |  |  |
| &nbsp;&nbsp;&nbsp;Opendoor Technologies, Inc.<sup>(a)</sup> | (7000) | $(18130) |
| &nbsp;&nbsp;&nbsp;**Multi Asset Class REITs — (2.49)%** |  |  |
| &nbsp;&nbsp;&nbsp;Vornado Realty Trust | (20000) | (471800) |
| &nbsp;&nbsp;&nbsp;**Non-Alcoholic Beverages — (0.15)%** |  |  |
| &nbsp;&nbsp;&nbsp;Oatly Group AB - ADR<sup>(a)</sup> | (12500) | (27500) |
| &nbsp;&nbsp;&nbsp;**Office REITs — (4.09)%** |  |  |
| &nbsp;&nbsp;&nbsp;Boston Properties, Inc. | (5200) | (378040) |
| &nbsp;&nbsp;&nbsp;Corporate Office Properties Trust | (15000) | (399749) |
|  |  | (777789) |
| &nbsp;&nbsp;&nbsp;**P&C Insurance — (0.18)%** |  |  |
| &nbsp;&nbsp;&nbsp;Lemonade, Inc.<sup>(a)</sup> | (1442) | (34896) |
| &nbsp;&nbsp;&nbsp;**Packaged Food — (0.13)%** |  |  |
| &nbsp;&nbsp;&nbsp;Beyond Meat, Inc.<sup>(a)</sup> | (1600) | (25120) |
| &nbsp;&nbsp;&nbsp;**Real Estate Services — (0.66)%** |  |  |
| &nbsp;&nbsp;&nbsp;Compass, Inc., Class A<sup>(a)</sup> | (47400) | (125136) |
| **TOTAL COMMON STOCKS – SHORT** |  |  |
| **(Proceeds Received $7,864,936)** |  | (6688550) |
| **EXCHANGE-TRADED FUNDS — SHORT — (1.26)%** |  |  |
| &nbsp;&nbsp;&nbsp;Direxion Daily Financial Bear 3X Shares<sup>(a)</sup> | (11700) | (239382) |
| **TOTAL EXCHANGE-TRADED FUNDS – SHORT** |  |  |
| **(Proceeds Received $499,663)** |  | (239382) |
| **TOTAL SECURITIES SOLD SHORT — (36.48)%** |  |  |
| **(Proceeds Received $8,364,599)** |  | $(6927932) |

---

*<sup>(a)</sup>* *Non-income producing security.* 

*ADR - American Depositary Receipt*

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> Semi-Annual Report \| October 31, 2022 11

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Statement of Assets and Liabilities</u> <br> *October 31, 2022 (Unaudited)*

---

| | |
|:---|:---|
| **ASSETS** | |
| Investments in securities at fair value (cost $16,745,174) | $18930692 |
| Deposit held by broker for securities sold short | 7613580 |
| Receivable for fund shares sold | 88 |
| Receivable for investments sold | 289696 |
| Dividends and interest receivable | 6973 |
| Prepaid expenses | 15458 |
| &nbsp;&nbsp;&nbsp;**Total Assets** | 26856487 |
| **LIABILITIES** |  |
| Bank overdraft | 6480 |
| Securities sold short, at value (proceeds received $8,364,599) | 6927932 |
| Payable for investments purchased | 884549 |
| Payable for dividends declared on short sales | 1200 |
| Payable to Adviser | 8594 |
| Payable to Administrator | 4291 |
| Payable to Directors | 147 |
| Other accrued expenses | 27071 |
| &nbsp;&nbsp;&nbsp;**Total Liabilities** | 7860264 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net Assets** | $18996223 |
| **Net Assets consist of:** |  |
| Paid-in capital | 17516842 |
| Accumulated earnings | 1479381 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net Assets** | $18996223 |
| Shares outstanding, par value $0.10 per share (30,000,000 authorized shares) | 680023 |
| **Net asset value, offering price and redemption price per share<sup>(a)</sup>** | $27.93 |

---

*<sup>(a)</sup>* *Redemption price may differ from net asset value if redemption fee is applied.*

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> 12 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Statement of Operations</u> <br> *For the six months ended October 31, 2022 (Unaudited)*

---

| | |
|:---|:---|
| **INVESTMENT INCOME** |  |
| &nbsp;&nbsp;&nbsp;Dividend income (net of foreign taxes withheld of $3,948) | $227796 |
| &nbsp;&nbsp;&nbsp;Interest income | 6676 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total investment income** | 234472 |
| **EXPENSES** |  |
| &nbsp;&nbsp;&nbsp;Investment Advisory fees | 95232 |
| &nbsp;&nbsp;&nbsp;Legal | 21269 |
| &nbsp;&nbsp;&nbsp;Miscellaneous | 18270 |
| &nbsp;&nbsp;&nbsp;Director's fees and expenses | 18148 |
| &nbsp;&nbsp;&nbsp;Registration | 13378 |
| &nbsp;&nbsp;&nbsp;Fund accounting | 11943 |
| &nbsp;&nbsp;&nbsp;Compliance Services | 9592 |
| &nbsp;&nbsp;&nbsp;Administration | 9369 |
| &nbsp;&nbsp;&nbsp;Transfer agent | 9369 |
| &nbsp;&nbsp;&nbsp;Audit and tax preparation | 9206 |
| &nbsp;&nbsp;&nbsp;Report printing | 6565 |
| &nbsp;&nbsp;&nbsp;Insurance | 4635 |
| &nbsp;&nbsp;&nbsp;Custodian | 3862 |
| &nbsp;&nbsp;&nbsp;Sub transfer agent fees | 1137 |
| &nbsp;&nbsp;&nbsp;Pricing | 872 |
| &nbsp;&nbsp;&nbsp;Interest | 16118 |
| &nbsp;&nbsp;&nbsp;Dividend expense on securities sold short | 82238 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total expenses** | 331203 |
| &nbsp;&nbsp;&nbsp;Fees contractually waived by Adviser | (42427) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net operating expenses** | 288776 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net investment loss** | (54304) |
| **NET REALIZED AND CHANGE IN UNREALIZED GAIN (LOSS) ON INVESTMENTS** |  |
| &nbsp;&nbsp;&nbsp;Net realized gain (loss) from: |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Investments | (181797) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Securities sold short | 239577 |
| &nbsp;&nbsp;&nbsp;Change in unrealized appreciation (depreciation) on: |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Investments | (724515) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Securities sold short | (216264) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Foreign currency | 2569 |
| **NET REALIZED AND CHANGE IN UNREALIZED LOSS ON INVESTMENTS, SECURITIES SOLD SHORT AND FOREIGN CURRENCY** | (880430) |
| **NET DECREASE IN NET ASSETS RESULTING FROM OPERATIONS** | $(934734) |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> Semi-Annual Report \| October 31, 2022 13

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Statements of Changes in Net Assets</u>

---

| | | |
|:---|:---|:---|
|  | **For the Six**<br>**Months Ended**<br>**October 31, 2022**<br>**(Unaudited)** |<br>**For the Year Ended**<br>**April 30, 2022** |
| **INCREASE (DECREASE) IN NET ASSETS DUE TO:** |  |  |
| **Operations** |  |  |
| &nbsp;&nbsp;&nbsp;Net investment loss | $(54304) | $(223025) |
| &nbsp;&nbsp;&nbsp;Net realized gain on investments, securities sold short and foreign currency transactions | 57780 | 473203 |
| &nbsp;&nbsp;&nbsp;Net change in unrealized depreciation of investments, securities sold short and foreign currency translations | (938210) | (143591) |
| **NET INCREASE (DECREASE) IN NET ASSETS RESULTING FROM OPERATIONS** | (934734) | 106587 |
| **CAPITAL TRANSACTIONS** |  |  |
| &nbsp;&nbsp;&nbsp;Proceeds from shares sold | 601086 | 283698 |
| &nbsp;&nbsp;&nbsp;Amount paid for shares redeemed | (549659) | (1478210) |
| &nbsp;&nbsp;&nbsp;Proceeds from redemption fees (Note 1) | 1742 | 2518 |
| **NET INCREASE (DECREASE) IN NET ASSETS RESULTING FROM CAPITAL TRANSACTIONS** | 53169 | (1191994) |
| **TOTAL DECREASE IN NET ASSETS** | (881565) | (1085407) |
| **NET ASSETS** |  |  |
| &nbsp;&nbsp;&nbsp;Beginning of period | 19877788 | 20963195 |
| &nbsp;&nbsp;&nbsp;End of period | $18996223 | $19877788 |
| **SHARE TRANSACTIONS** |  |  |
| &nbsp;&nbsp;&nbsp;Shares sold | 21626 | 9079 |
| &nbsp;&nbsp;&nbsp;Shares redeemed | (19872) | (49444) |
| &nbsp;&nbsp;&nbsp;**NET INCREASE (DECREASE) IN SHARES OUTSTANDING** | 1754 | (40365) |

---

 ****

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> 14 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Financial Highlights</u>

For a share outstanding during each period

---

| | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|
|  | **For the Six**<br>**Months**<br>**Ended**<br>**October 31,**<br>**2022**<br>**(Unaudited)** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2022** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2021** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2020** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2019** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2018** |
| **Selected Per Share Data** |  |  |  |  |  |  |
| **Net asset value, beginning of period** | $29.31 | $29.17 | $15.21 | $20.86 | $20.61 | $20.72 |
| **Investment operations:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net investment loss<sup>(a)</sup> | (0.08) | (0.32) | (0.10) | (0.20) | (0.19) | (0.24) |
| &nbsp;&nbsp;&nbsp;Net realized and unrealized gain (loss) on investments | (1.30) | 0.46 | 14.06 | (5.45) | 0.44 <sup>(b)</sup> | 0.13 <sup>(b)</sup> |
| **Total from investment operations** | (1.38) | 0.14 | 13.96 | (5.65) | 0.25 | (0.11) |
| **Paid-in capital from redemption fees** | — <sup>(c)</sup> | — <sup>(c)</sup> | — <sup>(c)</sup> | — <sup>(c)</sup> | — <sup>(c)</sup> | — <sup>(c)</sup> |
| **Net asset value, end of period** | $27.93 | $29.31 | $29.17 | $15.21 | $20.86 | $20.61 |
| **Total Return<sup>(d)</sup>** | (4.71)% <sup>(e)</sup> | 0.48% | 91.78% | (27.09)% | 1.21% | (0.53)% |
| **Ratios and Supplemental Data:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net assets, end of period (000 omitted) | $18996 | $19878 | $20963 | $12259 | $23272 | $49785 |
| **Ratios to Average Net Assets:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Ratio of net expenses to average net assets<sup>(f)</sup> | 3.03 % <sup>(g)</sup> | 3.07% | 3.56% | 3.60% | 3.19% | 2.41% |
| &nbsp;&nbsp;&nbsp;Ratio of expenses to average net assets before waiver by Adviser | 3.48 % <sup>(g)</sup> | 3.38% | 4.10% | 4.08% | 3.31% | 2.41% |
| &nbsp;&nbsp;&nbsp;Ratio of net investment loss to average net assets | (0.57)% <sup>(g)</sup> | (1.07)% | (0.47)% | (1.00)% | (0.92)% | (1.19)% |
| **Portfolio Turnover Rate** | 24 % <sup>(e)</sup> | 55% | 38% | 87% | 240% | 531% |

---

** 

*<sup>(a)</sup>* *Calculated using average shares outstanding.*

 

*<sup>(b)</sup>* *The amount shown for a share outstanding throughout the period does not accord with the change in aggregate gains and losses in the portfolio of securities during the period because of timing of sales and purchases of fund shares in relation to fluctuating market values during the period.*

*<sup>(c)</sup>* *Rounds to less than $0.005 per share.*

*<sup>(d)</sup>* *Total return in the above table represents the rate that the investor would have earned or lost on an investment in the Fund, assuming reinvestment of distributions.*

** 

*<sup>(e)</sup>* *Not annualized.*

*<sup>(f)</sup>* *Excluding dividend and interest expense, the ratios of net expenses to average net assets were 2.00% for the six months ended October 31, 2022 and 2.00%, 2.00%, 2.00%, 2.00% and 1.85% for the fiscal years ended April 30, 2022, 2021, 2020, 2019 and 2018, respectively.*

*<sup>(g)</sup>* *Annualized.*

*See accompanying notes which are an integral part of these financial statements.* <br>  <br> Semi-Annual Report \| October 31, 2022 15

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

**1.** **ORGANIZATION** 

The Caldwell & Orkin - Gator Capital Long/Short Fund (the "Fund"), is the only investment portfolio of The Caldwell & Orkin Funds, Inc. (the "Company"), an open-end, diversified management investment company registered under the Investment Company Act of 1940, as amended (the "1940 Act"), and incorporated under the laws of the State of Maryland on August 15, 1989. The Fund's investment objective is to provide long-term capital growth with a short-term focus on capital preservation. Gator Capital Management, LLC (the "Adviser"), the Fund's investment adviser, uses a fundamental driven, multi-dimensional investment process focusing on active allocation, security selection and surveillance to achieve the Fund's investment objective.

**2.** **SUMMARY OF SIGNIFICANT ACCOUNTING POLICIES** 

The Fund is an investment company and follows accounting and reporting guidance under Financial Accounting Standards Board Accounting Standards Codification ("ASC") Topic 946, "Financial Services-Investment Companies." The following is a summary of significant accounting policies followed by the Fund in the preparation of its financial statements. These policies are in conformity with generally accepted accounting principles in the United States of America ("GAAP").

**Use of Estimates**

The preparation of financial statements in conformity with GAAP requires management to make estimates and assumptions that affect the reported amounts of assets and liabilities and disclosure of contingent assets and liabilities at the date of the financial statements and the reported amounts of revenues and expenses during the reporting period. Actual results could differ from those estimates.

**Securities Valuation**

Securities are stated at the closing price on the date at which the net asset value ("NAV") is being determined. If the date of determination is not a trading date, or the closing price is not otherwise available, the last bid price for long positions and is the last ask price for short positions is used for a fair value instead. Debt securities are valued at the price provided by an independent pricing service. Any assets or securities for which market quotations are not readily available are valued at fair value as determined in good faith by or under the direction of the Fund's Board of Directors (the "Board") in accordance with the Fund's Fair Value Pricing Policy.

**Securities Transactions and Related Investment Income**

The Fund follows industry practice and records securities transactions on trade date for financial reporting purposes. Dividend income is recorded on the ex-dividend date. Realized gains and losses from investment transactions are determined using the specific identification method. Interest income which includes amortization of premium and accretion of discount, is accrued as earned.

16 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

**Fair Value Measurements**

A three-tier hierarchy has been established to classify fair value measurements for disclosure purposes. Inputs refer broadly to the assumptions that market participants would use in pricing the asset or liability, including assumptions about risk. Inputs may be observable or unobservable. Observable inputs are inputs that reflect the assumptions market participants would use in pricing the asset or liability that are developed based on market data obtained from sources independent of the reporting entity. Unobservable inputs are inputs that reflect the reporting entity's own assumptions about the assumptions market participants would use in pricing the asset or liability that are developed based on the best information available.

Various inputs are used in determining the value of the Fund's investments. These inputs are summarized in the three broad levels listed below.

● Level 1 – unadjusted quoted prices in active markets for identical investments and/or registered investment companies where the value per share is determined and published and is the basis for current transactions for identical assets or liabilities at the valuation date

● Level 2 – quoted prices which are not active quoted prices for similar assets or liabilities in active markets or inputs other than quoted process that are observable (either directly or indirectly) for substantially the full term of the asset of liability

● Level 3 – significant unobservable inputs (including the Fund's own assumptions in determining fair value of investments based on the best information available)

The inputs used to measure fair value may fall into different levels of the fair value hierarchy. In such cases, for disclosure purposes, the level in the fair value hierarchy which is reported, is determined based on the lowest level input that is significant to the fair value measurement in its entirety.

The following is a summary of the inputs used as of October 31, 2022 in valuing the Fund's investments carried at value:

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Investments in Securities** | **Level 1** | **Level 2** | **Level 3** | **Total** |
| **Assets** | | | | |
| Common Stocks | $17723493 | $— | $— | $17723493 |
| Preferred Stocks | 99079 |  |  | 99079 |
| Warrants | 19328 |  |  | 19328 |
| Money Market Funds | 1088792 |  |  | 1088792 |
| Total | $18930692 | $— | $— | $18930692 |
| **Liabilities** |  |  |  |  |
| Securities Sold Short |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Common Stocks | $(6688550) | $— | $— | $(6688550) |
| &nbsp;&nbsp;&nbsp;Exchange-Traded Funds | (239382) |  |  | (239382) |
| Total | $(6927932) | $— | $— | $(6927932) |

---

Semi-Annual Report \| October 31, 2022 17

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

Refer to the Fund's Schedule of Investments for a listing of the common stocks by industry type. The Fund did not hold any assets at any time during the reporting period in which significant unobservable inputs were used in determining fair value; therefore, no reconciliation of Level 3 securities is included for this reporting period.

In December 2020, the SEC adopted a rule providing a framework for fund valuation practices ("Rule 2a-5"). Rule 2a-5 establishes requirements for determining fair value in good faith for purposes of the 1940 Act. Rule 2a-5 will permit fund boards to designate certain parties to perform fair value determinations, subject to board oversight and certain other conditions. Rule 2a-5 also defines when market quotations are "readily available" for purposes of the 1940 Act and the threshold for determining whether a fund must fair value a security. In connection with Rule 2a-5, the SEC also adopted related recordkeeping requirements and is rescinding previously issued guidance, including with respect to the role of a board in determining fair value and the accounting and auditing of fund investments.

**Share Valuation**

The NAV per share of the Fund is calculated by dividing the sum of the value of the securities held by the Fund, plus cash or other assets, minus all liabilities (including estimated accrued expenses) by the total number of shares outstanding for the Fund, rounded to the nearest cent. The Fund's shares will not be priced on the days on which the New York Stock Exchange is closed for trading. The offering and redemption price per share for the Fund is equal to the Fund's NAV per share.

The Fund charges a 2.00% redemption fee on shares held less than 90 days. These fees are deducted from the redemption proceeds otherwise payable to the shareholder. The Fund will retain the fee charged as paid-in capital and such fees become part of the Fund's daily NAV calculation. For the six months ended October 31, 2022, the Fund recorded $1,742 in redemption fee proceeds.

**Federal Income Taxes**

The Fund makes no provision for federal income tax or excise tax. The Fund has qualified and intends to qualify each year as a regulated investment company ("RIC") under subchapter M of the Internal Revenue Code of 1986, as amended, by complying with the requirements applicable to RICs and by distributing substantially all of its taxable income. The Fund also intends to distribute sufficient net investment income and net capital gains, if any, so that it will not be subject to excise tax on undistributed income and gains. If the required amount of net investment income or gains is not distributed, the Fund could incur a tax expense

The Fund may be subject to taxes imposed by countries in which it invests. Such taxes are generally based on income and/or capital gains earned or repatriated. Taxes are accrued and applied to net investment income, net realized gains and unrealized appreciation as such income and/or gains are earned.

18 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

The Fund recognizes tax benefits or expenses of uncertain tax positions only when the position is "more likely than not" to be sustained assuming examination by tax authorities. Management of the Fund has reviewed tax positions taken in tax years that remain subject to examination by all major tax jurisdictions, including federal (i.e., the previous three tax year ends and the interim tax period since then, as applicable) and has concluded that no provision for unrecognized tax benefits or expenses is required in these financial statements and does not expect this to change over the next twelve months. The Fund recognizes interest and penalties, if any, related to unrecognized tax benefits as income tax expense in the Statement of Operations. During the year, the Fund did not incur any interest or penalties.

**3.** **FEES AND OTHER TRANSACTIONS WITH AFFILIATES AND OTHER SERVICE PROVIDERS** 

The Fund has entered into a management agreement (the "Management Agreement") with the Adviser pursuant to which the Adviser provides space, facilities, equipment and personnel necessary to perform administrative and investment management services for the Fund. The Management Agreement provides that the Adviser is responsible for the management of the Fund's portfolio. For such services and expenses assumed by the Adviser, the Fund pays a monthly advisory fee at incremental annual rates as follows:

---

| | |
|:---|:---|
| **Advisory Fee** | **Average Daily Net Assets** |
| 1.00% | Up to $250 million |
| 0.90% | In excess of $250 million but not greater than $500 million |
| 0.80% | In excess of $500 million |

---

The Adviser has agreed to reimburse the Fund through August 30, 2023 to the extent necessary to prevent the Fund's annual ordinary operating expenses (excluding taxes, expenses related to the execution of portfolio transactions and the investment activities of the Fund such as, for example, interest, dividend expenses on securities sold short, brokerage commissions and fees and expenses charged to the Fund by any investment company in which the Fund invests and extraordinary charges such as litigation costs) from exceeding 2.00% of the Fund's average net assets. For the six months ended October 31, 2022, the Adviser waived fees and reimbursed expenses in the amount of $42,427 for the Fund. During the six months ended October 31, 2022, the Adviser earned $95,232 from the Fund, before the waiver described above.

Ultimus Fund Solutions, LLC (the "Administrator") provides fund accounting, fund administration and transfer agency services under a Master Services Agreement to the Fund. The Fund pays the Administrator fees for its services under the Master Services Agreement. In addition, the Fund pays out-of-pocket expenses including, but not limited to postage, supplies and costs of pricing the Fund's securities. For the six months ended October 31, 2022, the Administrator earned fees of $9,369 for administration services, $11,943 for fund accounting services, and $9,369 for transfer agent services.

Semi-Annual Report \| October 31, 2022 19

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

Ultimus Fund Distributors, LLC (the "Distributor") serves as distributor to the Fund. The Fund does not pay the Distributor for these services. The Distributor is a wholly-owned subsidiary of the Administrator.

Certain officers of the Fund are also officers of the Administrator and the Distributor.

**4.** **DIRECTOR COMPENSATION** 

The Fund pays each Director, in cash, an annual fee of $8,000 per year, plus $1,500 for each in-person meeting attended and $1,000 for each telephonic meeting attended. The Fund also reimburses Directors' actual out-of-pocket expenses relating to attendance at meetings.

**5.** **INVESTMENT PORTFOLIO TRANSACTIONS** 

During the six months ended October 31, 2022, the Fund purchased $4,387,239 and sold $5,199,184 of securities, excluding securities sold short and short-term investments.

**Short Sales and Segregated Cash**

Short sales are transactions in which the Fund sells a security it does not own, in anticipation of a decline in the market value of that security. To initiate such a transaction, the Fund must borrow the security to deliver to the buyer upon the short sale; the Fund is then obligated to replace the security borrowed by purchasing it in the open market at some later date, completing the transaction.

The Fund will incur a loss if the market price of the security increases between the date of the short sale and the date on which the Fund replaces the borrowed security. The Fund will realize a gain if the security declines in value between those dates.

All short sales must be fully collateralized. The Fund maintains the collateral in segregated accounts consisting of cash and/or U.S. Government securities sufficient to collateralize the market value of its short positions. Typically, the segregated cash with brokers and other financial institutions exceeds the minimum required. Deposits with brokers for securities sold short are invested in money market instruments. Segregated cash is held at the custodian in the name of the broker per a tri-party agreement among the Fund, the custodian, and the broker.

The Fund may also sell short "against the box", i.e., the Fund enters into a short sale as described above, while holding an offsetting long position in the same security which it sold short. If the Fund enters into a short sale against the box, it will segregate an equivalent amount of securities owned by the Fund as collateral while the short sale is outstanding.

The Fund limits the value of its short positions (excluding short sales "against the box") to 60% of the Fund's total net assets. At October 31, 2022, the Fund had approximately 36% of its total net assets in short positions.

20 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

For the six months ended October 31, 2022, the cost of investments purchased to cover short sales and the proceeds from investments sold short were $1,669,324 and $3,540,247, respectively.

**6.** **FEDERAL TAX INFORMATION** 

As of October 31, 2022, the net unrealized appreciation (depreciation) of investments, including short securities, for tax purposes was as follows:

---

| | |
|:---|:---|
| Gross unrealized appreciation | $5742294 |
| Gross unrealized depreciation | (2321737) |
| Net unrealized appreciation on investments | $3420557 |
| Tax cost of investments | $8582203 |

---

At April 30, 2022, the Fund's most recent fiscal year end, the components of accumulated earnings (deficit) on a tax basis were as follows:

---

| | |
|:---|:---|
| Accumulated capital and other losses | $(1944652) |
| Unrealized appreciation | 4358767 |
| Total accumulated earnings (deficit) | $2414115 |

---

The difference between book basis and tax basis unrealized appreciation is attributable primarily to the tax deferral of wash losses and investments in partnerships and certain other investments.

Certain capital losses incurred after October 31, and within the current taxable year, are deemed to arise on the first business day of the Fund's following taxable year. Late year Ordinary Losses incurred after December 31 are deemed to arise on the first business day of the Fund's following taxable year. For the tax year ended April 30, 2022, the Fund deferred $96,638 in Qualified Late Year Ordinary Losses.

As of April 30, 2022, the Fund has available for tax purposes an unused capital loss carryforward of $1,848,014 of short-term capital losses with no expiration, which is available to offset against future taxable net capital gains.

**7.** **COMMITMENTS AND CONTINGENCIES** 

Under the Fund's organizational documents, its officers and directors are indemnified against certain liability arising out of the performance of their duties to the Fund. Additionally, in the normal course of business, the Fund enters into contracts with service providers that may contain general indemnification clauses, which may permit indemnification to the extent

Semi-Annual Report \| October 31, 2022 21

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2022 (Unaudited)*

permissible under applicable law. The Fund's maximum exposure under these arrangements is unknown, as this would involve future claims that may be made against the Fund that have not yet occurred.

**8.** **SUBSEQUENT EVENTS** 

Management of the Fund has evaluated the need for disclosures and/or adjustments resulting from subsequent events through the date at which these financial statements were issued. Based upon this evaluation, management has determined there were no items requiring adjustment of the financial statements or additional disclosure.

22 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - <br> <u>Gator Capital Long/Short Fund</u> <u>Disclosure of Fund Expenses</u> <br> *October 31, 2022 (Unaudited)*

We believe it is important for you to understand the impact of fees and expenses on your investment in the Fund. As a shareholder of the Fund, you incur two types of costs: (1) transaction costs related to the purchase and redemption of Fund shares, including redemption fees and brokerage commissions (if applicable); and (2) ongoing costs, including management fees, administrative expenses, portfolio transaction costs and other Fund expenses. A mutual fund's ongoing costs are expressed as a percentage of its average net assets. This figure is known as the expense ratio. The following example is intended to help you understand your ongoing costs (in dollars and cents) of investing in the Fund and to compare these costs with the ongoing costs of investing in other mutual funds.

The below example is based on an investment of $1,000 invested at the beginning of the period and held for the entire period indicated, May 1, 2022 through October 31, 2022. The table below illustrates the Fund's expenses in two ways:

**Based on Actual Fund Returns**

The first line of the table below provides information about actual account values and actual expenses. You may use the information in this line, together with the amount you invested, to estimate the expenses that you paid over the period. Simply divide your account value by $1,000 (for example, an $8,600 account value divided by $1,000 = 8.6), then multiply the result by the number in the first line under the heading entitled "Expenses Paid During the Period" to estimate the expenses you paid on your account during this period.

**Based on a Hypothetical 5% Return for Comparison Purposes**

Expenses shown in the table are meant to highlight your ongoing costs only and do not reflect any transactional costs. Therefore, the second line of the table below is useful in comparing ongoing costs only and will not help you determine the relative costs of owning different funds. In addition, if transaction costs were included, your costs would have been higher.

---

| | | | | |
|:---|:---|:---|:---|:---|
|  | **Beginning**<br>**Account Value**<br>**May 1, 2022** | **Ending**<br>**Account Value**<br>**October 31, 2022** | **Expenses**<br>**Paid During**<br>**the Period<sup>(a)</sup>** | **Annualized**<br>**Expense**<br>**Ratio** |
| Actual | $1000.00 | $952.90 | $14.93 | 3.03% |
| Hypothetical<sup>(b)</sup> | $1000.00 | $1009.92 | $15.37 | 3.03% |

---

<sup>(a)</sup> Expenses are equal to the Fund's annualized expense ratios, multiplied by the average account value over the period, multiplied by 184/365 (to reflect the one-half year period).

<sup>(b)</sup> Hypothetical assumes 5% annual return before expenses.

Semi-Annual Report \| October 31, 2022 23

Caldwell & Orkin - Director Approval of the <br> <u>Gator Capital Long/Short Fund</u> <u>Investment Advisory Agreement</u> <br> *October 31, 2022 (Unaudited)*

At a meeting held in person on June 7, 2022, at which all of the Directors were present, the Board, including the Directors who are not "interested persons," as defined by the Investment Company Act of 1940, as amended (the "1940 Act") (the "Independent Directors"), of Caldwell & Orkin Funds, Inc. (the "Company"), voting separately, reviewed and approved the investment advisory agreement with Gator Capital Management, LLC (the "Adviser") (the "Management Agreement"). In the course of their deliberations, the Board was advised by legal counsel. The Board received and reviewed a substantial amount of information provided by the Adviser in response to requests of the Board and legal counsel.

In considering the approval of the Management Agreement and reaching their conclusions with respect thereto, the Board was briefed by counsel on its fiduciary duties and responsibilities in reviewing and approving the Management Agreement and the types of information that should be reviewed by them and their responsibilities in making an informed decision regarding the approval of the Management Agreement. The Board also reviewed and analyzed various factors that the Directors determined were relevant, including: (1) the nature, extent and quality of the services to be provided by the Adviser to the Caldwell & Orkin – Gator Capital Long/Short Fund (the "Fund") and the Adviser's experience managing registered investment companies; (2) the performance of the Adviser in managing investments for clients of the Adviser other than the Fund; (3) the costs of the services to be provided and profits to be realized by the Adviser from its relationship with the Fund, as well as fee rates charged by the Adviser and other advisers for comparable strategies; (4) the extent to which economies of scale may be realized as the Fund grows and whether management fee levels reflect these economies of scale for the benefit of the Fund's investors; and (5) other benefits to be derived by the Adviser from its relationship with the Fund. The Board's analysis of the foregoing factors included, but was not limited to, the following:

<u>Nature, Extent and Quality of Services</u>. The Board considered the operating and investment advisory services provided by the Adviser to the Fund, including, without limitation, its investment advisory services, its coordination of services for the Fund among the Fund's service providers, its compliance procedures and practices, its efforts to promote the Fund and assist in its distribution and its provision of officers for the Company. Based on the foregoing information, the Board determined that the nature, extent, and quality of the management and advisory services provided by the Adviser were appropriate for the Fund.

<u>Performance of the Fund and the Adviser</u>. The Board considered the investment performance of the Adviser in managing investments for the Fund on an absolute basis and also compared the performance of the Fund with the performance of the peer group funds managed by other advisors. The Board also considered the consistency of the Adviser's management of the Fund with the Fund's investment objective and policies, and long- term performance of the Fund. Following its evaluation of the Adviser's performance and that of the Fund in such capacities, the Board concluded that the performance of both the Adviser and the Fund was satisfactory.

24 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

Caldwell & Orkin - Director Approval of the <br> <u>Gator Capital Long/Short Fund</u> <u>Investment Advisory Agreement</u> <br> *October 31, 2022 (Unaudited)*

<u>Cost of Services and Projected Profits of the Adviser with respect to the Fund</u>. In reviewing the cost of services and the profitability that the Adviser derives from its relationship with the Fund, the Board considered that continuing the Management Agreement would result in no changes to the fees charged to the Fund, and that the services provided in exchange for such fees would be appropriate. Additionally, the Board discussed the Adviser's staffing, personnel and methods of operating; the financial condition of the Adviser and the level of commitment to the Fund and the Adviser by the principals of the Adviser; the asset level of the Fund; and the overall fees and expenses of the Fund.

The Board next considered the fees and expenses of the Fund, and then compared them to other funds similar in terms of the type of fund, the style of investment management, the size of the fund and the nature of the fund's investment strategy, among other factors. The Board observed that the management fee charged by the Adviser is generally below the average charged by its peers (as chosen by the Adviser) and that the Fund's expense ratio was higher than the average of its peers. In addition, the Directors took note of the expense limitation provisions within the Management Agreement and the financial capacity of the Adviser to fulfill its obligations under the Management Agreement. Following these comparisons and considerations as well as further discussion of the foregoing, the Board determined that the fees paid to the Adviser by the Fund under the Management Agreement are appropriate and within the range of what would have been negotiated at arm's length.

<u>Economies of Scale</u>. Following discussion of the Fund's asset level, expectations for growth, levels of fees, and the expense limitation agreement, the Board concluded that the Fund's fee arrangement was appropriate, and that the Fund's overall fee structure provided for savings and protection for shareholders at lower asset levels through the Fund's expense limitation agreement that is part of the Management Agreement.

<u>Other Benefits Derived by the Adviser from its Relationship with the Fund</u>. The Board considered that (other than the advisory fee) there are no material "fall-out" or ancillary benefits that accrue to the Adviser as a result of its relationship with the Fund. Based on the foregoing information, the Board concluded that such potential benefits are immaterial to its consideration and approval of the Management Agreement.

After considering the above factors as well as other factors, the Board unanimously concluded that the terms of the Management Agreement were fair and reasonable and approved the Management Agreement for a one-year renewal period.

Semi-Annual Report \| October 31, 2022 25

**CUSTOMER PRIVACY NOTICE**

---

| | | | |
|:---|:---|:---|:---|
| &nbsp;&nbsp;**FACTS** | &nbsp;&nbsp;WHAT DOES CALDWELL & ORKIN FUNDS, INC. DO WITH YOUR PERSONAL INFORMATION? | &nbsp;&nbsp;WHAT DOES CALDWELL & ORKIN FUNDS, INC. DO WITH YOUR PERSONAL INFORMATION? | &nbsp;&nbsp;WHAT DOES CALDWELL & ORKIN FUNDS, INC. DO WITH YOUR PERSONAL INFORMATION? |
| &nbsp;&nbsp;**Why?** | &nbsp;&nbsp;Financial companies choose how they share your personal information. Federal law gives consumers the right to limit some but not all sharing. Federal law also requires us to tell you how we collect, share, and protect your personal information. Please read this notice carefully to understand what we do. | &nbsp;&nbsp;Financial companies choose how they share your personal information. Federal law gives consumers the right to limit some but not all sharing. Federal law also requires us to tell you how we collect, share, and protect your personal information. Please read this notice carefully to understand what we do. | &nbsp;&nbsp;Financial companies choose how they share your personal information. Federal law gives consumers the right to limit some but not all sharing. Federal law also requires us to tell you how we collect, share, and protect your personal information. Please read this notice carefully to understand what we do. |
| &nbsp;&nbsp;**What?** | &nbsp;&nbsp;The types of personal information we collect and share depend on the product or service you have with us. This information can include:<br>■ Social Security number<br>■ Assets<br>■ Retirement Assets<br>■ Transaction History<br>■ Checking Account Information<br>■ Purchase History<br>■ Account Balances<br>■ Account Transactions<br>■ Wire Transfer Instructions<br>When you are *no longer* our customer, we continue to share your information as described in this notice. | &nbsp;&nbsp;The types of personal information we collect and share depend on the product or service you have with us. This information can include:<br>■ Social Security number<br>■ Assets<br>■ Retirement Assets<br>■ Transaction History<br>■ Checking Account Information<br>■ Purchase History<br>■ Account Balances<br>■ Account Transactions<br>■ Wire Transfer Instructions<br>When you are *no longer* our customer, we continue to share your information as described in this notice. | &nbsp;&nbsp;The types of personal information we collect and share depend on the product or service you have with us. This information can include:<br>■ Social Security number<br>■ Assets<br>■ Retirement Assets<br>■ Transaction History<br>■ Checking Account Information<br>■ Purchase History<br>■ Account Balances<br>■ Account Transactions<br>■ Wire Transfer Instructions<br>When you are *no longer* our customer, we continue to share your information as described in this notice. |
| &nbsp;&nbsp;**How?** | &nbsp;&nbsp;All financial companies need to share your personal information to run their everyday business. In the section below, we list the reasons financial companies can share their customers' personal information; the reasons Caldwell & Orkin Funds, Inc. chooses to share; and whether you can limit this sharing. | &nbsp;&nbsp;All financial companies need to share your personal information to run their everyday business. In the section below, we list the reasons financial companies can share their customers' personal information; the reasons Caldwell & Orkin Funds, Inc. chooses to share; and whether you can limit this sharing. | &nbsp;&nbsp;All financial companies need to share your personal information to run their everyday business. In the section below, we list the reasons financial companies can share their customers' personal information; the reasons Caldwell & Orkin Funds, Inc. chooses to share; and whether you can limit this sharing. |
| &nbsp;&nbsp;**Reasons we can share your personal information** | &nbsp;&nbsp;**Reasons we can share your personal information** | &nbsp;&nbsp;**Does Caldwell &<br> Orkin Funds, Inc.<br> share?** | &nbsp;&nbsp;**Can you limit<br> this sharing?** |
| &nbsp;&nbsp;**For our everyday business purposes –** <br> Such as to process your transactions, maintain your account(s), respond to court orders and legal investigations, or report to credit bureaus | &nbsp;&nbsp;**For our everyday business purposes –** <br> Such as to process your transactions, maintain your account(s), respond to court orders and legal investigations, or report to credit bureaus | &nbsp;&nbsp;Yes | &nbsp;&nbsp;No |
| &nbsp;&nbsp;**For our marketing purposes –** <br> to offer our products and services to you | &nbsp;&nbsp;**For our marketing purposes –** <br> to offer our products and services to you | &nbsp;&nbsp;Yes | &nbsp;&nbsp;No |
| &nbsp;&nbsp;**For joint marketing with other financial companies** | &nbsp;&nbsp;**For joint marketing with other financial companies** | &nbsp;&nbsp;No | &nbsp;&nbsp;We don't share |
| &nbsp;&nbsp;**For our affiliates' everyday business purposes –** <br> information about your transactions and experiences | &nbsp;&nbsp;**For our affiliates' everyday business purposes –** <br> information about your transactions and experiences | &nbsp;&nbsp;No | &nbsp;&nbsp;No |
| &nbsp;&nbsp;**For our affiliates' everyday business purposes –** <br> information about your creditworthiness | &nbsp;&nbsp;**For our affiliates' everyday business purposes –** <br> information about your creditworthiness | &nbsp;&nbsp;No | &nbsp;&nbsp;We don't share |
| &nbsp;&nbsp;**For nonaffiliates to market to you** | &nbsp;&nbsp;**For nonaffiliates to market to you** | &nbsp;&nbsp;No | &nbsp;&nbsp;We don't share |
| &nbsp;&nbsp;**For our affiliates' marketing purposes** | &nbsp;&nbsp;**For our affiliates' marketing purposes** | &nbsp;&nbsp;Yes | &nbsp;&nbsp;Yes\* |
| &nbsp;&nbsp;**Questions?** | &nbsp;&nbsp;Call (800) 467-7903 | &nbsp;&nbsp;Call (800) 467-7903 | &nbsp;&nbsp;Call (800) 467-7903 |
| &nbsp;&nbsp;**To limit our <br> sharing** | &nbsp;&nbsp;\*Call (813) 282-7870<br>Please note: <br> If you are a *new* customer, we can begin sharing your information 30 days from the date we sent this notice. When you are *no longer* our customer, we continue to share your information as described in this notice. However, you can contact us at any time to limit our sharing. | &nbsp;&nbsp;\*Call (813) 282-7870<br>Please note: <br> If you are a *new* customer, we can begin sharing your information 30 days from the date we sent this notice. When you are *no longer* our customer, we continue to share your information as described in this notice. However, you can contact us at any time to limit our sharing. | &nbsp;&nbsp;\*Call (813) 282-7870<br>Please note: <br> If you are a *new* customer, we can begin sharing your information 30 days from the date we sent this notice. When you are *no longer* our customer, we continue to share your information as described in this notice. However, you can contact us at any time to limit our sharing. |

---

26 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

---

| | |
|:---|:---|
| &nbsp;&nbsp;**Page 2** |  |
| &nbsp;&nbsp;**Who we are** | &nbsp;&nbsp;**Who we are** |
| &nbsp;&nbsp;**Who is providing this** <br> **notice?** | &nbsp;&nbsp;Caldwell & Orkin Funds, Inc.<br> Caldwell & Orkin - Gator Capital Long/Short Fund<br> Ultimus Fund Distributors, LLC (Distributor)<br> Ultimus Fund Solutions, LLC (Administrator) |
| &nbsp;&nbsp;**What we do** | &nbsp;&nbsp;**What we do** |
| &nbsp;&nbsp;**How does Caldwell** <br> **& Orkin Funds, Inc.** <br> **protect my personal** <br> **information?** | &nbsp;&nbsp;To protect your personal information from unauthorized access and use, we use security measures that comply with federal law. These measures include computer safeguards and secured files and buildings.<br>Our service providers are held accountable for adhering to strict policies and procedures to prevent any misuse of your nonpublic personal information. |
| &nbsp;&nbsp;**How does Caldwell <br> & Orkin Funds, Inc. <br> collect my personal <br> information?** | &nbsp;&nbsp;We collect your personal information, for example, when you<br>■ Open an account<br>■ Provide account information<br>■ Give us your contact information<br>■ Make deposits or withdrawals from your account<br>■ Make a wire transfer<br>■ Tell us where to send the money<br>■ Tell us who receives the money<br>■ Show your government-issued ID<br>■ Show your driver's license<br>We also collect your personal information from other companies. |
| &nbsp;&nbsp;**Why can't I limit all <br> sharing?** | &nbsp;&nbsp;Federal law gives you the right to limit only<br>■ Sharing for affiliates' everyday business purposes – information about your creditworthiness<br>■ Affiliates from using your information to market to you<br>■ Sharing for nonaffiliates to market to you<br>State laws and individual companies may give you additional rights to limit sharing. |
| &nbsp;&nbsp;**Definitions** | &nbsp;&nbsp;**Definitions** |
| &nbsp;&nbsp;**Affiliates** | &nbsp;&nbsp;Companies related by common ownership or control. They can be financial and nonfinancial companies.<br>■ Gator Capital Management, LLC *the investment adviser to Caldwell & Orkin Funds, Inc., could be deemed an affiliate.*  |
| &nbsp;&nbsp;**Nonaffiliates** | &nbsp;&nbsp;Companies not related by common ownership or control. They can be financial and nonfinancial companies<br>■ *Caldwell & Orkin Funds, Inc. does not share with nonaffiliates so they can market to you.*  |
| &nbsp;&nbsp;**Joint marketing** | &nbsp;&nbsp;A formal agreement between nonaffiliated financial companies that together market financial products or services to you.<br>■ *Caldwell & Orkin Funds, Inc. does not jointly market.* |

---

Semi-Annual Report \| October 31, 2022 27

This Page is Intentionally Left Blank.

This Page is Intentionally Left Blank.

<u>CALDWELL & ORKIN - GATOR CAPITAL LONG/SHORT FUND</u> <br> *Semi-Annual Report to Shareholders*

---

| | | |
|:---|:---|:---|
| &nbsp;&nbsp;**BOARD OF DIRECTORS** <br> Frederick T. Blumer,<br> Independent Chairman<br> Derek Pilecki, President<br> Bevin E. Newton<br> Rhett E. Ingerick<br>**INVESTMENT ADVISER** <br> Gator Capital Management, LLC<br> 100 S. Ashley Drive,<br> Suite 895<br> Tampa, FL 33602<br>**DISTRIBUTOR** <br> Ultimus Fund Distributors, LLC<br> 225 Pictoria Drive, Suite 450<br> Cincinnati, OH 45246 | &nbsp;&nbsp;**TRANSFER, REDEMPTION** <br> **& DIVIDEND** <br> **DISBURSING AGENT** <br> Ultimus Fund Solutions, LLC<br> P.O. Box 46707<br> Cincinnati, OH 45246-0707<br>**CUSTODIAN** <br> U.S. Bank, N.A.<br> 425 Walnut Street<br> Cincinnati, OH 45202 | &nbsp;&nbsp;**LEGAL COUNSEL** <br> Kilpatrick Townsend &<br> Stockton LLP<br> 1001 West Fourth Street<br> Winston-Salem, NC<br> 27101-2400 |

---

The Caldwell & Orkin - Gator Capital Long/Short Fund's (the "Fund") portfolio may or may not have positions in any of the companies referenced in this Report to Shareholders as of any date after October 31, 2022. The commentary reflects the views of the investment manager through the end of the period or through the date of this report, as the case may be. Of course, these views are subject to change as market and other conditions warrant. These financial statements are submitted for the general information of the Fund's shareholders. **They are not authorized for distribution to prospective investors unless preceded or accompanied by an effective Fund Prospectus.**

**Availability of Proxy Voting Policy & Procedures, Proxy Voting Record and Code of Ethics** - A description of a) the policies and procedures the Fund uses to determine how to vote proxies relating to portfolio securities, b) how the Fund voted proxies relating to portfolio securities during the most recent 12-month period ended June 30, and c) the Code of Ethics applicable to the principal officers of the Fund are available without charge, upon request, by calling toll-free (800) 467-7903, or on the Securities and Exchange Commission's website at www.sec.gov.

Fund Information - For more information about the Fund please call (800) 467-7903 or visit the Fund's website at https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/.

---

| |
|:---|
| **Gator Capital Management, LLC** |
| 100 S. Ashley Drive, Suite 895 |
| Tampa, FL 33602 |

---

Gator-SAR-22

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) Not applicable.

**Item 2. Code of Ethics.**

Not applicable to semiannual reports.

**Item 3. Audit Committee Financial Expert.**

Not applicable to semiannual reports.

**Item 4. Principal Accountant Fees and Services.**

Not applicable to semiannual reports.

**Item 5.** **Audit Committee of Listed Registrants.**

Not applicable.

**Item 6.** **Investments.**

(a) Included as part of the report to Stockholders filed under Item 1 of this Form.

(b) Not applicable.

**Item 7. Disclosure of Proxy Voting Policies and Procedures for Closed-End Management Investment Companies.**

Not applicable.

**Item 8. Portfolio Managers of Closed-End Management Investment Companies.**

Not applicable.

**Item 9. Purchases of Equity Securities by Closed-End Management Investment Company and Affiliated Purchasers.**

Not applicable.

**Item 10. Submission of Matters to a Vote of Security Holders.**

None.

**Item 11. Controls and Procedures.**

(a) The registrant's Principal Executive Officer and Principal Financial Officer have concluded that the registrant's disclosure controls and procedures (as defined in Rule 30a-3(c) under the Act) are effective in design and operation and are sufficient to form the basis of the certifications required by Rule 30a-2 under the Act, based on their evaluation of these disclosure controls and procedures within 90 days of the filing of this report on Form N-CSR.

(b) There were no changes in the registrant's internal control over financial reporting (as defined in Rule 30a-3(d) under the Act (17 CFR 270.30a-3(d)) that occurred during the second fiscal quarter of the period covered by this report that have materially affected or are reasonably likely to materially affect, the registrant's internal control over financial reporting.

**Item 12. Disclosure of Securities Lending Activities for Closed-End Management Investment Companies.**

Not applicable.

**Item 13. Exhibits.**

(a)(1) Not applicable.

[(a)(2) Certifications pursuant to Rule 30a-2(a) are attached hereto.](cert1.htm)

(a)(3) Not applicable.

(a)(4) Not applicable.

[(b) Certifications pursuant to Rule 30a-2(b) are furnished herewith.](cert2.htm)

**SIGNATURES**

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, the registrant has duly caused this report to be signed on its behalf by the undersigned, thereunto duly authorized.

(Registrant) <u>The Caldwell & Orkin Funds, Inc.</u> 

---

| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp;/s/ Derek Pilecki |

---

Derek Pilecki, President and Principal Executive Officer

Date <u>1/6/2023 </u>

Pursuant to the requirements of the Securities Exchange Act of 1934 and the Investment Company Act of 1940, this report has been signed below by the following persons on behalf of the registrant and in the capacities and on the dates indicated.

---

| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp;/s/ Derek Pilecki |

---

Derek Pilecki, President and Principal Executive Officer

Date <u>1/6/2023 </u>

---

| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp;/s/ Zachary P. Richmond |

---

Zachary P. Richmond, Treasurer and Principal Financial Officer

Date <u>1/6/2023 </u>

## Ex-99.Cert

<u>CERTIFICATIONS</u>

I, Derek Pilecki, certify that:

1. I have reviewed this report on Form N-CSR of The Caldwell & Orkin Funds, Inc. (the "registrant");

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations, changes in net assets, and cash flows (if the financial statements are required to include a statement of cash flows) of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Rule 30a-3(c) under the Investment Company Act of 1940) and internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940) for the registrant and have:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of a date within 90 days prior to the filing date of this report based on such evaluation; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the period covered by this report that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize, and report financial information; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

<u>1/6/2023____</u> <u>/s/ Derek Pilecki</u>______________________________ <br> Date Derek Pilecki

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;President and Principal Executive Officer

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Caldwell & Orkin Funds, Inc.

<u>CERTIFICATIONS</u>

I, Zachary P. Richmond, certify that:

1. I have reviewed this report on Form N-CSR of The Caldwell & Orkin Funds, Inc. (the "registrant");

2. Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

3. Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations, changes in net assets, and cash flows (if the financial statements are required to include a statement of cash flows) of the registrant as of, and for, the periods presented in this report;

4. The registrant's other certifying officer and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Rule 30a-3(c) under the Investment Company Act of 1940) and internal control over financial reporting (as defined in Rule 30a-3(d) under the Investment Company Act of 1940) for the registrant and have:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b) Designed such internal control over financial reporting, or caused such internal control over financial reporting to be designed under our supervision, to provide reasonable assurance regarding the reliability of financial reporting and the preparation of financial statements for external purposes in accordance with generally accepted accounting principles;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c) Evaluated the effectiveness of the registrant's disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of a date within 90 days prior to the filing date of this report based on such evaluation; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;d) Disclosed in this report any change in the registrant's internal control over financial reporting that occurred during the period covered by this report that has materially affected, or is reasonably likely to materially affect, the registrant's internal control over financial reporting; and

5. The registrant's other certifying officer and I have disclosed to the registrant's auditors and the audit committee of the registrant's board of directors (or persons performing the equivalent functions):

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a) All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant's ability to record, process, summarize, and report financial information; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b) Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant's internal control over financial reporting.

<u>1/6/2023____</u> <u>/s/ Zachary P. Richmond_______________________</u><br> Date Zachary P. Richmond

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Treasurer and Principal Financial Officer

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;The Caldwell & Orkin Funds, Inc.

## Exhibit 99.906

This certification is provided pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, 18 U.S.C. § 1350, and accompanies the report on Form N-CSR for the period ended October 31, 2022 of The Caldwell & Orkin Funds, Inc. (the "Registrant").

I, Derek Pilecki, the President and Principal Executive Officer of the Registrant, certify that, to the best of my knowledge:

&nbsp;&nbsp;&nbsp;&nbsp;1. the Form N-CSR fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange
Act of 1934 (15 U.S.C. 78m(a) or 78o(d)); and

&nbsp;&nbsp;&nbsp;&nbsp;2. the information contained in the Form N-CSR fairly presents, in all material respects, the financial
condition and results of operations of the Registrant.

<u>1/6/2023 ____</u>

Date

<u>/s/ Derek Pilecki ______________________</u>

Derek Pilecki

President and Principal Executive Officer

The Caldwell & Orkin Funds, Inc.

This certification is being furnished solely pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 and is not being filed as part of Form N-CSR or as a separate disclosure document. A signed original of this written statement required by Section 906 has been provided to the Registrant and will be retained by the Registrant and furnished to the Securities and Exchange Commission or its staff upon request.

This certification is provided pursuant to Section 906 of the Sarbanes-Oxley Act of 2002, 18 U.S.C. § 1350, and accompanies the report on Form N-CSR for the period ended October 31, 2022 of The Caldwell & Orkin Funds, Inc. (the "Registrant").

I, Zachary P. Richmond, the Treasurer and Principal Financial Officer of the Registrant, certify that, to the best of my knowledge:

&nbsp;&nbsp;&nbsp;&nbsp;1. the Form N-CSR fully complies with the requirements of Section 13(a) or 15(d) of the Securities Exchange
Act of 1934 (15 U.S.C. 78m(a) or 78o(d)); and

&nbsp;&nbsp;&nbsp;&nbsp;2. the information contained in the Form N-CSR fairly presents, in all material respects, the financial
condition and results of operations of the Registrant.

<u>1/6/2023 ____</u>

Date

<u>/s/ Zachary P. Richmond ______________________</u>

Zachary P. Richmond

Treasurer and Principal Financial Officer

The Caldwell & Orkin Funds, Inc.

This certification is being furnished solely pursuant to Section 906 of the Sarbanes-Oxley Act of 2002 and is not being filed as part of Form N-CSR or as a separate disclosure document. A signed original of this written statement required by Section 906 has been provided to the Registrant and will be retained by the Registrant and furnished to the Securities and Exchange Commission or its staff upon request.