# EDGAR Filing Document

**Accession Number:** 0000864230
**File Stem:** 0001580642-25-008038
**Filing Date:** 2025-12
**Character Count:** 63511
**Document Hash:** 135c838c64bc90fa8f4a6203f59f0233
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001580642-25-008038.hdr.sgml**: 20251229

**ACCESSION NUMBER**: 0001580642-25-008038

**CONFORMED SUBMISSION TYPE**: N-CSRS

**PUBLIC DOCUMENT COUNT**: 17

**CONFORMED PERIOD OF REPORT**: 20251031

**FILED AS OF DATE**: 20251229

**DATE AS OF CHANGE**: 20251229

**EFFECTIVENESS DATE**: 20251229

**FILER**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** CALDWELL & ORKIN FUNDS INC
- **CENTRAL INDEX KEY:** 0000864230

**ORGANIZATION NAME:**
- **EIN:** 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:** 251607367

**BUSINESS ADDRESS:**
- **STREET 1:** 2502 N. ROCKY POINT DRIVE
- **STREET 2:** SUITE 665
- **CITY:** TAMPA
- **STATE:** FL
- **ZIP:** 33607
- **BUSINESS PHONE:** 813-282-7870

**MAIL ADDRESS:**
- **STREET 1:** 2502 N. ROCKY POINT DRIVE
- **STREET 2:** SUITE 665
- **CITY:** TAMPA
- **STATE:** FL
- **ZIP:** 33607

**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           |

?xml version='1.0' encoding='ASCII'?

---

| |
|:---|
| **UNITED STATES** |
| **SECURITIES AND EXCHANGE COMMISSION** |
| **WASHINGTON, D.C. 20549** |
| **FORM N-CSR** |
| **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 |
| Tampa, Florida 33602 |
| (Address of principal executive offices)(Zip code) |
| Derek Pilecki |
| 2502 N. Rocky Point Drive, Suite 665 |
| Tampa, Florida 33607 |
| (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, 2025</u>

Form N-CSR is to be used by management investment companies to file reports with the Commission not later than 10 days after the transmission to stockholders of any report that is required to be transmitted to stockholders under Rule 30e-1 under the Investment Company Act of 1940 (17 CFR 270.30e-1). The Commission may use the information provided on Form N-CSR in its regulatory, disclosure review, inspection and policymaking roles.

A registrant is required to disclose the information specified by Form N-CSR, and the Commission will make this information public. A registrant is not required to respond to the collection of information contained in Form N-CSR unless the Form displays a currently valid Office of Management and Budget ("OMB") control number. Please direct comments concerning the accuracy of the information collection burden estimate and any suggestions for reducing the burden to Secretary, Securities and Exchange Commission, 450 Fifth Street, NW, Washington, DC 20549-0609. The OMB has reviewed this collection of information under the clearance requirements of 44 U.S.C. § 3507.

**Item 1. Reports to Stockholders.**

(a) Tailored Shareholder Reports

# Gator Capital Long/Short Fund
(GATRX)

# Semi-Annual Shareholder Report - October 31, 2025
![Image](i9d60839065c279cc86f47b77.jpg)

## Fund Overview
This semi-annual shareholder report contains important information about Gator Capital Long/Short Fund (the "Fund") for the period of May 1, 2025 to October 31, 2025. You can find additional information about the Fund at https://funddocs.filepoint.com/gator/. You can also request this information by contacting us at (800) 467-7903.

## What were the Fund's costs for the last six months?

### (based on a hypothetical $10,000 investment)

---

| | | |
|:---|:---|:---|
| **Fund Name** | **Costs of a $10,000 investment** | **Costs paid as a percentage of a $10,000 investment** |
| Gator Capital Long/Short Fund | $149 | 2.68% |

---

## What did the Fund invest in?

## **Sector Weighting (% of net assets)<sup>Footnote Reference \*</sup>**![Group By Sector Chart](iba5eec2a3a469ed4957f6235.jpg)

---

| | |
|:---|:---|
| **Value** | **Value** |
| Investment Companies | 0.1% |
| Casinos & Gaming | 0.3% |
| Pharmaceuticals | 0.7% |
| Insurance Brokers & Services | 1.0% |
| Computer Hardware & Storage | 1.2% |
| Money Market | 1.7% |
| Internet Media & Services | 1.9% |
| Mortgage Finance | 2.2% |
| Investment Management | 2.5% |
| Data Processing | 2.9% |
| Private Equity | 3.7% |
| Institutional Brokerage | 4.2% |
| Real Estate Services | 4.3% |
| Life Insurance | 4.5% |
| Consumer Finance | 5.9% |
| Data & Transaction Processors | 6.4% |
| Diversified Banks | 8.1% |
| Wealth Management | 11.4% |
| Banks | 21.7% |

---

---

| | |
|:---|:---|
| Footnote | Description |
| Footnote<sup>\*</sup> | The net percentages are computed by taking the net dollar exposure, including short positions, and dividing by the net assets of the Fund. Consequently, the percentages will not total to 100%. |

---

## **Fund Statistics** 
* Net Assets$68,646,081

* Number of Portfolio Holdings98

* Advisory Fee $315,608

* Portfolio Turnover50%

## Material Fund Changes
No material changes occurred during the period ended October 31, 2025.

![Image](i9d60839065c279cc86f47b77.jpg)

# Gator Capital Long/Short Fund (GATRX)

# Semi-Annual Shareholder Report - October 31, 2025

## Where can I find additional information about the Fund?
Additional information is available on the Fund's website (https://funddocs.filepoint.com/gator/), including its:

* Prospectus

* Financial information

* Holdings

* Proxy voting information

TSR-SAR 103125-GATRX

(b) Not applicable

**Item 2. Code of Ethics.**

Not applicable – disclosed with annual report

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

Not applicable – disclosed with annual report

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

Not applicable – disclosed with annual report

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

Not applicable – disclosed with annual report

**Item 6. Investments.**

The Registrant's schedule of investments in unaffiliated issuers is included in the Financial Statements under Item 7 of this form.

**Item 7. Financial Statements and Financial Highlights for Open-End Management Investment Companies.**

(a) ![(COVERPAGE)](ca001_v1.jpg)

<u>**Table of Contents**</u> <u>Gator Capital Long/Short Fund</u> <br> *October 31, 2025 (Unaudited)*

---

| | |
|:---|:---|
| Schedule of Investments | 2 |
| Schedule of Securities Sold Short | 6 |
| Statement of Assets and Liabilities | 9 |
| Statement of Operations | 10 |
| Statements of Changes in Net Assets | 11 |
| Financial Highlights | 12 |
| Notes to Financial Statements | 13 |
| Additional Information | 20 |

---

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **COMMON STOCKS — LONG — 92.26%** |  |  |
| &nbsp;&nbsp;&nbsp;**Banks — 32.30%** |  |  |
| &nbsp;&nbsp;&nbsp;Alerus Financial Corp. | 15100 | $318912 |
| &nbsp;&nbsp;&nbsp;Axos Financial, Inc.<sup>(a)</sup> | 25000 | 1949500 |
| &nbsp;&nbsp;&nbsp;Banc of California, Inc. | 56600 | 960502 |
| &nbsp;&nbsp;&nbsp;Bridgewater Bancshares, Inc.<sup>(a)</sup> | 24000 | 395040 |
| &nbsp;&nbsp;&nbsp;Business First Bancshares, Inc. | 10408 | 255204 |
| &nbsp;&nbsp;&nbsp;Capital Bancorp, Inc. | 19915 | 553537 |
| &nbsp;&nbsp;&nbsp;Chain Bridge Bancorp, Inc.<sup>(a)</sup> | 24900 | 738036 |
| &nbsp;&nbsp;&nbsp;Commercial Bancgroup, Inc.<sup>(a)</sup> | 29200 | 713940 |
| &nbsp;&nbsp;&nbsp;ConnectOne Bancorp, Inc. | 66360 | 1596622 |
| &nbsp;&nbsp;&nbsp;Customers Bancorp, Inc.<sup>(a)</sup> | 27200 | 1825664 |
| &nbsp;&nbsp;&nbsp;Dime Community Bancshares, Inc. | 22000 | 577500 |
| &nbsp;&nbsp;&nbsp;First Business Financial Services, Inc. | 7500 | 379575 |
| &nbsp;&nbsp;&nbsp;First Citizens BancShares, Inc., Class A | 900 | 1642338 |
| &nbsp;&nbsp;&nbsp;First Financial Bancorp | 53000 | 1240730 |
| &nbsp;&nbsp;&nbsp;First Internet Bancorp | 10000 | 177400 |
| &nbsp;&nbsp;&nbsp;Homestreet, Inc.<sup>(a)</sup> | 59000 | 790010 |
| &nbsp;&nbsp;&nbsp;Meta Financial Group, Inc. | 8369 | 569594 |
| &nbsp;&nbsp;&nbsp;OFG Bancorp | 34800 | 1345368 |
| &nbsp;&nbsp;&nbsp;Old Second Bancorp, Inc. | 43900 | 788005 |
| &nbsp;&nbsp;&nbsp;OP Bancorp | 38573 | 514950 |
| &nbsp;&nbsp;&nbsp;UMB Financial Corp. | 16000 | 1710080 |
| &nbsp;&nbsp;&nbsp;Unity Bancorp, Inc. | 5051 | 229366 |
| &nbsp;&nbsp;&nbsp;Webster Financial Corp. | 15000 | 855600 |
| &nbsp;&nbsp;&nbsp;Western Alliance Bancorp | 26400 | 2042040 |
|  |  | 22169513 |
| &nbsp;&nbsp;&nbsp;**Casinos & Gaming — 0.26%** |  |  |
| &nbsp;&nbsp;&nbsp;Caesars Entertainment, Inc.<sup>(a)</sup> | 9000 | 180900 |
| &nbsp;&nbsp;&nbsp;**Computer Hardware & Storage — 1.21%** |  |  |
| &nbsp;&nbsp;&nbsp;Dell Technologies, Inc., Class C | 4000 | 648040 |
| &nbsp;&nbsp;&nbsp;Hewlett Packard Enterprise Co. | 7500 | 183150 |
|  |  | 831190 |
| &nbsp;&nbsp;&nbsp;**Consumer Finance — 5.01%** |  |  |
| &nbsp;&nbsp;&nbsp;Navient Corp. | 55000 | 672650 |
| &nbsp;&nbsp;&nbsp;SLM Corp. | 68000 | 1825800 |
| &nbsp;&nbsp;&nbsp;Synchrony Financial | 12600 | 937188 |
|  |  | 3435638 |

---

*See accompanying notes which are an integral part of these financial statements.*

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

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Data & Transaction Processors — 6.46%** |  |  |
| &nbsp;&nbsp;&nbsp;Block, Inc.<sup>(a)</sup> | 4800 | $364512 |
| &nbsp;&nbsp;&nbsp;Fiserv, Inc.<sup>(a)</sup> | 5000 | 333450 |
| &nbsp;&nbsp;&nbsp;Global Payments, Inc. | 21000 | 1632960 |
| &nbsp;&nbsp;&nbsp;Visa, Inc., Class A | 1900 | 647406 |
| &nbsp;&nbsp;&nbsp;WEX, Inc.<sup>(a)</sup> | 10000 | 1458800 |
|  |  | 4437128 |
| &nbsp;&nbsp;&nbsp;**Data Processing & Outsourced Services — 2.89%** |  |  |
| &nbsp;&nbsp;&nbsp;PayPal Holdings, Inc.<sup>(a)</sup> | 28600 | 1981122 |
| &nbsp;&nbsp;&nbsp;**Diversified Banks — 8.98%** |  |  |
| &nbsp;&nbsp;&nbsp;Barclays PLC - ADR | 108000 | 2320920 |
| &nbsp;&nbsp;&nbsp;BNP Paribas SA - ADR<sup>(a)</sup> | 45500 | 1752205 |
| &nbsp;&nbsp;&nbsp;Societe Generale SA - ADR | 165000 | 2095500 |
|  |  | 6168625 |
| &nbsp;&nbsp;&nbsp;**Institutional Brokerage — 4.18%** |  |  |
| &nbsp;&nbsp;&nbsp;Interactive Brokers Group, Inc., Class A | 40800 | 2870688 |
| &nbsp;&nbsp;&nbsp;**Insurance Brokers & Services — 1.00%** |  |  |
| &nbsp;&nbsp;&nbsp;Kingstone Companies, Inc. | 47000 | 685260 |
| &nbsp;&nbsp;&nbsp;**Internet Media & Services — 1.89%** |  |  |
| &nbsp;&nbsp;&nbsp;Meta Platforms, Inc., Class A | 2000 | 1296700 |
| &nbsp;&nbsp;&nbsp;**Investment Companies — 0.19%** |  |  |
| &nbsp;&nbsp;&nbsp;BBX Capital, Inc.<sup>(a)</sup> | 32801 | 129072 |
| &nbsp;&nbsp;&nbsp;**Investment Management — 3.01%** |  |  |
| &nbsp;&nbsp;&nbsp;Invesco Ltd. | 75000 | 1777500 |
| &nbsp;&nbsp;&nbsp;WisdomTree Investments, Inc. | 24074 | 287925 |
|  |  | 2065425 |
| &nbsp;&nbsp;&nbsp;**Life Insurance — 4.47%** |  |  |
| &nbsp;&nbsp;&nbsp;Genworth Financial, Inc., Class A<sup>(a)</sup> | 160000 | 1350400 |
| &nbsp;&nbsp;&nbsp;Jackson Financial, Inc. | 17000 | 1713770 |
|  |  | 3064170 |
| &nbsp;&nbsp;&nbsp;**P&C Insurance — 0.35%** |  |  |
| &nbsp;&nbsp;&nbsp;Hippo Holdings, Inc.<sup>(a)</sup> | 6606 | 242969 |

---

*See accompanying notes which are an integral part of these financial statements.*

Semi-Annual Financial Statements \| October 31, 2025 3

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Private Equity — 3.69%** |  |  |
| &nbsp;&nbsp;&nbsp;The Carlyle Group, Inc. | 20000 | $1066400 |
| &nbsp;&nbsp;&nbsp;Victory Capital Holdings, Inc., Class A | 23590 | 1468949 |
|  |  | 2535349 |
| &nbsp;&nbsp;&nbsp;**Real Estate Services — 4.30%** |  |  |
| &nbsp;&nbsp;&nbsp;Anywhere Real Estate, Inc.<sup>(a)</sup> | 294000 | 2954700 |
| &nbsp;&nbsp;&nbsp;**Specialty & Generic Pharmaceuticals — 0.69%** |  |  |
| &nbsp;&nbsp;&nbsp;Viatris, Inc. | 46000 | 476560 |
| &nbsp;&nbsp;&nbsp;**Wealth Management — 11.38%** |  |  |
| &nbsp;&nbsp;&nbsp;Ameriprise Financial, Inc. | 2500 | 1131925 |
| &nbsp;&nbsp;&nbsp;Robinhood Markets, Inc., Class A<sup>(a)</sup> | 14700 | 2157666 |
| &nbsp;&nbsp;&nbsp;Stifel Financial Corp. | 12000 | 1421160 |
| &nbsp;&nbsp;&nbsp;UBS Group AG | 46000 | 1764560 |
| &nbsp;&nbsp;&nbsp;Virtus Investment Partners, Inc. | 8200 | 1335124 |
|  |  | 7810435 |
| **TOTAL COMMON STOCKS — LONG—** |  |  |
| **(Cost $42,936,115)** |  | 63335444 |
| **PREFERRED STOCKS — LONG — 4.29%** |  |  |
| &nbsp;&nbsp;&nbsp;**Specialty Finance — 4.29%** |  |  |
| &nbsp;&nbsp;&nbsp;AG Mortgage Investment Trust, Inc., Series C, 8.00% | 36000 | 908266 |
| &nbsp;&nbsp;&nbsp;Chimera Investment Corp., Series B, 8.00% | 14391 | 345528 |
| &nbsp;&nbsp;&nbsp;Chimera Investment Corp., Series D, 8.00% | 19717 | 474982 |
| &nbsp;&nbsp;&nbsp;Federal National Mortgage Association, Series O, 7.00% | 5243 | 151785 |
| &nbsp;&nbsp;&nbsp;Federal National Mortgage Association, Series R, 7.63% | 30185 | 437682 |
| &nbsp;&nbsp;&nbsp;SLM Corp., Series B, 1.70% | 8276 | 624755 |
|  |  | 2942998 |
| **TOTAL PREFERRED STOCKS — LONG—** |  |  |
| **(Cost $1,976,682)** |  | 2942998 |

---

*See accompanying notes which are an integral part of these financial statements.*

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

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Investments</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **MONEY MARKET FUNDS — 1.72%** |  |  |
| &nbsp;&nbsp;&nbsp;First American Government Obligations Fund — Class X, 3.92%<sup>(b)</sup> | 1181752 | $1181752 |
| **TOTAL MONEY MARKET FUNDS** |  |  |
| **(Cost $1,181,752)** |  | 1181752 |
| **TOTAL INVESTMENTS — 98.27%** |  |  |
| **(Cost $46,094,549)** |  | 67460194 |
| **Other Assets in Excess of Liabilities — 1.73%** |  | 1185887 |
| **NET ASSETS — 100.00%** |  | $68646081 |

---

*(a)* *Non-income producing security.* 

*(b)* *Rate disclosed is the seven day effective yield as of October 31, 2025.* 

 

*ADR - American Depositary Receipt*

*See accompanying notes which are an integral part of these financial statements.*

Semi-Annual Financial Statements \| October 31, 2025 5

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Securities Sold Short</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **COMMON STOCKS — SHORT — (20.65)%** |  |  |
| &nbsp;&nbsp;&nbsp;**Banks — (10.46)%** |  |  |
| &nbsp;&nbsp;&nbsp;Bank of Hawaii Corp. | (10000) | $(649300) |
| &nbsp;&nbsp;&nbsp;Citigroup, Inc. | (14000) | (1417220) |
| &nbsp;&nbsp;&nbsp;First Financial Bankshares, Inc. | (6250) | (193063) |
| &nbsp;&nbsp;&nbsp;Hingham Institution for Savings | (1712) | (503773) |
| &nbsp;&nbsp;&nbsp;Merchants Bancorp | (20000) | (623800) |
| &nbsp;&nbsp;&nbsp;Midland States Bankcorp, Inc. | (26841) | (392952) |
| &nbsp;&nbsp;&nbsp;Northwest Bancshares, Inc. | (9142) | (107053) |
| &nbsp;&nbsp;&nbsp;Park National Corp. | (1700) | (258723) |
| &nbsp;&nbsp;&nbsp;Renasant Corp. | (17800) | (598614) |
| &nbsp;&nbsp;&nbsp;Stock Yards Bancorp, Inc. | (6519) | (423865) |
| &nbsp;&nbsp;&nbsp;Toronto-Dominion Bank (The) | (15000) | (1231950) |
| &nbsp;&nbsp;&nbsp;Wells Fargo & Co. | (9000) | (782730) |
|  |  | (7183043) |
| &nbsp;&nbsp;&nbsp;**Commercial Vehicles — (0.00)%** |  |  |
| &nbsp;&nbsp;&nbsp;Nikola Corp.<sup>(a)</sup> | (333) | (4) |
| &nbsp;&nbsp;&nbsp;**Diversified Banks — (0.96)%** |  |  |
| &nbsp;&nbsp;&nbsp;U.S. Bancorp | (14100) | (658188) |
| &nbsp;&nbsp;&nbsp;**Industrial Wholesale & Rental — (0.66)%** |  |  |
| &nbsp;&nbsp;&nbsp;SiteOne Landscape Supply, Inc.<sup>(a)</sup> | (3500) | (454195) |
| &nbsp;&nbsp;&nbsp;**Insurance Brokers — (0.35)%** |  |  |
| &nbsp;&nbsp;&nbsp;Arthur J. Gallagher & Co. | (960) | (239510) |
| &nbsp;&nbsp;&nbsp;**Investment Companies — (0.07)%** |  |  |
| &nbsp;&nbsp;&nbsp;TriplePoint Venture Growth BDC Corp. | (8500) | (46495) |
| &nbsp;&nbsp;&nbsp;**Investment Management — (0.52)%** |  |  |
| &nbsp;&nbsp;&nbsp;T. Rowe Price Group, Inc. | (3500) | (358855) |
| &nbsp;&nbsp;&nbsp;**Mass Merchants — (0.44)%** |  |  |
| &nbsp;&nbsp;&nbsp;Walmart, Inc. | (3000) | (303540) |

---

*See accompanying notes which are an integral part of these financial statements.*

6 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Securities Sold Short</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| &nbsp;&nbsp;&nbsp;**Mortgage Finance — (1.23)%** |  |  |
| &nbsp;&nbsp;&nbsp;AGNC Investment Corp. | (14600) | $(146000) |
| &nbsp;&nbsp;&nbsp;Essent Group Ltd. | (9000) | (545130) |
| &nbsp;&nbsp;&nbsp;Federal National Mortgage Association<sup>(a)</sup> | (15600) | (159276) |
|  |  | (850406) |
| &nbsp;&nbsp;&nbsp;**Non-Alcoholic Beverages — (0.02)%** |  |  |
| &nbsp;&nbsp;&nbsp;Oatly Group AB - ADR<sup>(a)</sup> | (782) | (12348) |
| &nbsp;&nbsp;&nbsp;**Office REITs — (1.22)%** |  |  |
| &nbsp;&nbsp;&nbsp;Corporate Office Properties Trust | (15000) | (422550) |
| &nbsp;&nbsp;&nbsp;Cousins Properties, Inc. | (16000) | (414880) |
|  |  | (837430) |
| &nbsp;&nbsp;&nbsp;**P&C Insurance — (3.90)%** |  |  |
| &nbsp;&nbsp;&nbsp;American International Group, Inc. | (12000) | (947520) |
| &nbsp;&nbsp;&nbsp;NMI Holdings, Inc., Class A<sup>(a)</sup> | (19291) | (702771) |
| &nbsp;&nbsp;&nbsp;ProAssurance Corp. | (10235) | (245128) |
| &nbsp;&nbsp;&nbsp;Radian Group, Inc. | (23000) | (780620) |
|  |  | (2676039) |
| &nbsp;&nbsp;&nbsp;**Packaged Food — (0.00)%** |  |  |
| &nbsp;&nbsp;&nbsp;Beyond Meat, Inc.<sup>(a)</sup> | (1600) | (2648) |
| &nbsp;&nbsp;&nbsp;**Regional Banks — (0.82)%** |  |  |
| &nbsp;&nbsp;&nbsp;KeyCorp | (32000) | (562880) |
| **TOTAL COMMON STOCKS — SHORT** |  |  |
| **(Proceeds Received $13,699,020)** |  | (14185581) |

---

*See accompanying notes which are an integral part of these financial statements.*

Semi-Annual Financial Statements \| October 31, 2025 7

<u>Gator Capital Long/Short Fund</u> <u>Schedule of Securities Sold Short</u> <br> *October 31, 2025 (Unaudited)*

---

| | | |
|:---|:---|:---|
|  | **Shares** | **Fair Value** |
| **EXCHANGE-TRADED FUNDS — SHORT — (9.63)%** |  |  |
| &nbsp;&nbsp;&nbsp;Direxion Daily Financial Bear 3X Shares | (1170) | $(51714) |
| &nbsp;&nbsp;&nbsp;Global X Nasdaq 100 Covered Call ETF | (188900) | (3292527) |
| &nbsp;&nbsp;&nbsp;Global X S&P 500 Covered Call ETF | (82000) | (3266060) |
|  |  | (6610301) |
| **TOTAL EXCHANGE-TRADED FUNDS — SHORT** |  |  |
| **(Proceeds Received $6,779,821)** |  | (6610301) |
| **TOTAL SECURITIES SOLD SHORT — (30.28)%** |  |  |
| **(Proceeds Received $20,478,841)** |  | $(20795882) |

---

*(a)* *Non-income producing security.* 

 

*ADR - American Depositary Receipt*

 

*ETF - Exchange-Traded Fund*

*See accompanying notes which are an integral part of these financial statements.*

8 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

<u>Gator Capital Long/Short Fund</u> <u>Statement of Assets and Liabilities</u> <br> *October 31, 2025 (Unaudited)*

---

| | |
|:---|:---|
| **ASSETS** |  |
| Investments is securities at fair value (cost $46,094,549) | $67460194 |
| Deposit held by broker for securities sold short | 21107069 |
| Receivable for fund shares sold | 83164 |
| Receivable for investments sold | 847772 |
| Dividends and interest receivable | 24137 |
| Tax reclaims receivable | 15479 |
| Prepaid expenses | 26737 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total Assets** | 89564552 |
| **LIABILITIES** |  |
| Bank overdraft | 11247 |
| Securities sold short, at value (proceeds received $20,478,841) | 20795882 |
| Payable for fund shares redeemed | 25097 |
| Payable for dividends declared on short sales | 1752 |
| Payable to Adviser | 59300 |
| Payable to Administrator | 9076 |
| Other accrued expenses | 16117 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total Liabilities** | 20918471 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net Assets** | $68646081 |
| **Net Assets consist of:** |  |
| Paid-in capital | 41229416 |
| Accumulated earnings | 27416665 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net Assets** | $68646081 |
| Shares outstanding, par value $0.10 per share (30,000,000 authorized shares) | 1168004 |
| **Net asset value, offering price and redemption price per share**<sup>(a)</sup>** | $58.77 |

---

*<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.*

Semi-Annual Financial Statements \| October 31, 2025 9

<u>Gator Capital Long/Short Fund</u> <u>Statement of Operations</u> <br> *For the six months ended October 31, 2025 (Unaudited)*

---

| | |
|:---|:---|
| **INVESTMENT INCOME** |  |
| &nbsp;&nbsp;&nbsp;Dividend income (net of foreign taxes withheld of $30,689) | $910209 |
| &nbsp;&nbsp;&nbsp;Interest income | 56615 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Total investment income** | 966824 |
| **EXPENSES** |  |
| &nbsp;&nbsp;&nbsp;Investment Advisory fees | 315608 |
| &nbsp;&nbsp;&nbsp;Legal | 25665 |
| &nbsp;&nbsp;&nbsp;Director's fees and expenses | 24901 |
| &nbsp;&nbsp;&nbsp;Administration | 22986 |
| &nbsp;&nbsp;&nbsp;Transfer agent | 17894 |
| &nbsp;&nbsp;&nbsp;Registration | 15174 |
| &nbsp;&nbsp;&nbsp;Fund accounting | 14301 |
| &nbsp;&nbsp;&nbsp;Miscellaneous | 13808 |
| &nbsp;&nbsp;&nbsp;Compliance Services | 9326 |
| &nbsp;&nbsp;&nbsp;Audit and tax preparation | 8877 |
| &nbsp;&nbsp;&nbsp;Report printing | 6478 |
| &nbsp;&nbsp;&nbsp;Sub transfer agent fees | 6095 |
| &nbsp;&nbsp;&nbsp;Insurance | 5914 |
| &nbsp;&nbsp;&nbsp;Custodian | 4240 |
| &nbsp;&nbsp;&nbsp;Pricing | 943 |
| &nbsp;&nbsp;&nbsp;Dividend expense on securities sold short | 354680 |
| &nbsp;&nbsp;&nbsp;**Total expenses** | 846890 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net operating expenses** | 846890 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net investment income** | 119934 |
| **NET REALIZED AND CHANGE IN UNREALIZED** |  |
| &nbsp;&nbsp;&nbsp;**GAIN (LOSS) ON INVESTMENTS** |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net realized gain from: |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Investments | 3425283 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Securities sold short | 594086 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Foreign currency transactions | 208 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Change in unrealized appreciation (depreciation) on: |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Investments | 7027172 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Securities sold short | (317057) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Foreign currency transactions | (14) |
| **NET REALIZED AND CHANGE IN UNREALIZED GAIN ON INVESTMENTS AND SECURITIES SOLD SHORT** | 10729678 |
| **NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS** | $10849612 |

---

*See accompanying notes which are an integral part of these financial statements.*

10 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

<u>Gator Capital Long/Short Fund</u> <u>Statements of Changes in Net Assets</u>

---

| | | |
|:---|:---|:---|
|  | **For the Six**<br>**Months Ended**<br>**October 31, 2025**<br>**(Unaudited)** | <br>**For the Year Ended**<br>**April 30, 2025** |
| **INCREASE (DECREASE) IN NET ASSETS DUE TO:** |  |  |
| **Operations** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net investment income | $119934 | $282452 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net realized gain on investments, securities sold short and foreign currency transactions | 4019577 | 2373315 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Net change in unrealized appreciation of investments, securities sold short and foreign currency translations | 6710101 | 3179152 |
| **NET INCREASE IN NET ASSETS RESULTING FROM OPERATIONS** | 10849612 | 5834919 |
| **DISTRIBUTIONS TO SHAREHOLDERS FROM:** |  |  |
| Earnings |  | (386411) |
| **CAPITAL TRANSACTIONS** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Proceeds from shares sold | 11513130 | 19384129 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Reinvestment of distributions |  | 383502 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Amount paid for shares redeemed | (3598439) | (9193791) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Proceeds from redemption fees (Note 1) | 8979 | 26373 |
| **NET INCREASE IN NET ASSETS RESULTING FROM CAPITAL TRANSACTIONS** | 7923670 | 10600213 |
| **TOTAL INCREASE IN NET ASSETS** | 18773282 | 16048721 |
| **NET ASSETS** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Beginning of period | 49872799 | 33824078 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;End of period | $68646081 | $49872799 |
| **SHARE TRANSACTIONS** |  |  |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Shares sold | 199972 | 389736 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Shares issued in reinvestment of distributions |  | 7365 |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;Shares redeemed | (62213) | (187306) |
| &nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;**Net increase in shares outstanding** | 137759 | 209795 |

---

*See accompanying notes which are an integral part of these financial statements.*

Semi-Annual Financial Statements \| October 31, 2025 11

<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>**2025**<br>**(Unaudited)** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2025** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2024** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2023** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2022** |<br>**For the**<br>**Year**<br>**Ended**<br>**April 30,**<br>**2021** |
| **Selected Per Share Data** |  |  |  |  |  |  |
| **Net asset value, beginning of period** | $48.41 | $41.23 | $30.62 | $29.31 | $29.17 | $15.21 |
| **Investment operations:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net investment income<sup>(a)</sup> | 0.07 | 0.31 | 0.53 | (0.04) | (0.32) | (0.10) |
| &nbsp;&nbsp;&nbsp;Net realized and unrealized gain (loss) on investments | 10.29 | 7.25 | 10.08 | 1.35 | 0.46 | 14.06 |
| **Total from investment operations** | 10.36 | 7.56 | 10.61 | 1.31 | 0.14 | 13.96 |
| **Less distributions to shareholders from:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net investment income |  | (0.41) |  |  |  |  |
| **Total distributions** |  | (0.41) |  |  |  |  |
| **Paid-in capital from redemption fees** | — <sup>(b)</sup> | 0.03 | — <sup>(b)</sup> | — <sup>(b)</sup> | — <sup>(b)</sup> | — <sup>(b)</sup> |
| **Net asset value, end of period** | $58.77 | $48.41 | $41.23 | $30.62 | $29.31 | $29.17 |
| **Total Return<sup>(c)</sup>** | 2.13 %<sup>(d)</sup> | 18.33% | 34.65% | 4.47% | 0.48% | 91.78% |
| **Ratios and Supplemental Data:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Net assets, end of period (000 omitted) | $68646 | $49873 | $33824 | $20364 | $19878 | $20963 |
| **Ratios to Average Net Assets:** |  |  |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Ratio of net expenses to average net assets<sup>(e)</sup> | 2.68 %<sup>(f)</sup> | 2.62% | 3.07% | 3.13% | 3.07% | 3.56% |
| &nbsp;&nbsp;&nbsp;Ratio of expenses to average net assets before waiver by Adviser | 2.68 %<sup>(f)</sup> | 2.62% | 3.19% | 3.55% | 3.38% | 4.10% |
| &nbsp;&nbsp;&nbsp;Ratio of net investment income (loss) to average net assets | 0.38 %<sup>(f)</sup> | 0.65% | 1.51% | (0.12)% | (1.07)% | (0.47)% |
| **Portfolio Turnover Rate** | 50 %<sup>(d)</sup> | 42% | 40% | 52% | 55% | 38% |

---

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

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

*<sup>(c)</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>(d)</sup>* *Not annualized.*

*<sup>(e)</sup>* *Excluding dividend and interest expense, the ratios of net expenses to average net assets were 1.56% for the six months ended October 31, 2025 and 1.73%, 2.00%, 2.00%, 2.00% and 2.00% for the fiscal years ended April 30, 2025, 2024, 2023, 2022 and 2021, respectively.*

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

*See accompanying notes which are an integral part of these financial statements.*

12 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

**1.** **ORGANIZATION** 

The 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 Fund's investment adviser (the "Adviser"), uses a fundamental driven, multi-dimensional investment process focusing on active allocation, security selection and surveillance to achieve the Fund's investment objective.

The Fund operates as a single operating segment. The Fund's income, expenses, assets, and performance are regularly monitored and assessed as a whole by the Adviser, who is responsible for the oversight functions of the Fund, using the information presented in the financial statements and financial highlights.

**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 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.

Semi-Annual Financial Statements \| October 31, 2025 13

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

**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.

**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, 2025 in valuing the Fund's investments carried at value:

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Investments in Securities** | **Level 1** | **Level 2** | **Level 3** | **Total** |
| **Assets** | | | | |
| Common Stocks\* | $63335444 | $— | $— | $63335444 |
| Preferred Stocks\* | 2942998 |  |  | 2942998 |
| Money Market Funds | 1181752 |  |  | 1181752 |
| Total | $67460194 | $— | $— | $67460194 |

---

14 1-800-467-7903 \| https://gatorcapital.com/mutual-funds/gator-capital-long-short-fund/

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

---

| | | | | |
|:---|:---|:---|:---|:---|
| **Investments in Securities** | **Level 1** | **Level 2** | **Level 3** | **Total** |
| **Liabilities** | | | | |
| Securities Sold Short |  |  |  |  |
| &nbsp;&nbsp;&nbsp;Common Stocks\* | $(14185581) | $— | $— | $(14185581) |
| &nbsp;&nbsp;&nbsp;Exchange-Traded Funds | (6610301) |  |  | (6610301) |
| Total | $(20795882) | $— | $— | $(20795882) |

---

\* *Refer to the Schedule of Investments for industry classifications.*

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.

**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 fiscal six months ended October 31, 2025 the Fund recorded $8,979 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.

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

Semi-Annual Financial Statements \| October 31, 2025 15

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

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 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. During the six months ended October 31, 2025, the Adviser earned $315,608 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, 2025, the Administrator earned fees of $22,986 for administration services, $14,301 for fund accounting services and $17,894 for transfer agent services.

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.

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

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

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

The Fund pays each Director, in cash, an annual fee of $14,000 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, 2025, the Fund purchased $17,585,822 and sold $11,093,372 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 between 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, 2025, the Fund had approximately 21% of its total net assets in short positions.

For the six months ended October 31, 2025, the cost of investments purchased to cover short sales and the proceeds from investments sold short were $11,984,469 and $2,505,733, respectively.

Semi-Annual Financial Statements \| October 31, 2025 17

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

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

As of October 31, 2025, the net unrealized appreciation (depreciation) of investments, including short securities, for tax purposes was as follows:

---

| | |
|:---|:---|
| Gross unrealized appreciation | $23937656 |
| Gross unrealized depreciation | (3113655) |
| Net unrealized appreciation on investments | $20824001 |
| Tax cost of investments | $25829064 |

---

The tax character of distributions paid for the fiscal year ended April 30, 2025, the Fund's most recent fiscal year end, was as follows:

---

| | |
|:---|:---|
| Distributions paid from: |  |
| Ordinary income | $386411 |
| Total distributions paid | $386411 |

---

At April 30, 2025, the components of accumulated earnings (deficit) on a tax basis were as follows:

---

| | |
|:---|:---|
| Undistributed ordinary income | $282233 |
| Undistributed long term capital gains | 2170919 |
| Unrealized appreciation on investments | 14113900 |
| Total accumulated earnings | $16567052 |

---

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, 2025, the Fund did not defer any Qualified Late Year Ordinary Losses.

As of April 30, 2025, the Fund did not have any capital loss carryforwards available to offset against future taxable net capital gains. Capital loss carryforwards do not have an expiration date.

For the fiscal year ended April 30, 2025, the Fund utilized $399,453 in short term capital loss carryforwards.

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

<u>Gator Capital Long/Short Fund</u> <u>Notes to Financial Statements</u> <br> *October 31, 2025 (Unaudited)*

GAAP requires that certain components of net assets relating to permanent differences be reclassified between financial and tax reporting. These reclassifications have no effect on net assets or net asset value per share. There were no reclassifications for the tax year ended April 30, 2025.

**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 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.

Semi-Annual Financial Statements \| October 31, 2025 19

<u>Gator Capital Long/Short Fund</u> <u>Additional Information *(Unaudited)*</u> <br> *October 31, 2025*

**Changes in and Disagreements with Accountants**

There were no changes in or disagreements with accountants during the period covered by this report.

**Proxy Disclosures**

Not applicable.

**Remuneration Paid to Directors, Officers and Others**

Refer to the financial statements included herein.

**Statement Regarding Basis for Approval of Investment Advisory Agreement**

Not applicable.

**PROXY VOTING**

A description of the policies and procedures that the Trust uses to determine how to vote proxies relating to portfolio securities and information regarding how the Fund voted those proxies during the most recent six month period ended October 31, are available (1) without charge upon request by calling the Fund at 1-800-467-7903 and (2) in Fund documents filed with the SEC on the SEC's website at www.sec.gov.

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

GATOR CAPITAL LONG/SHORT FUND

**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 6-month period ended October 31, 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** 2502 N. Rocky Point Drive, Suite 665

Tampa, FL 33607

**Item 8. Changes in and Disagreements with Accountants for Open-End Management Investment Companies.**

Not applicable

**Item 9. Proxy Disclosures for Open-End Management Investment Companies.**

Not applicable

**Item 10. Remuneration Paid to Directors, Officers, and Others of Open-End Management Investment Companies.**

Included under Item 7

**Item 11. Statement Regarding Basis for Approval of Investment Advisory Contract.**

Included under Item 7

**Item 12. Disclosure of Proxy Voting Policies and Procedures for Closed-End Management Investment Companies.**

Not applicable

**Item 13. Portfolio Managers of Closed-End Management Investment Companies.**

Not applicable

**Item 14. Purchases of Equity Securities by Closed-End Management Investment Company and Affiliated Purchasers.**

Not applicable

**Item 15. Submission of Matters to a Vote of Security Holders.**

None

**Item 16. 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 as of a date within 90 days 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) during 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 17. Disclosure of Securities Lending Activities for Closed-End Management Investment Companies.**

Not applicable

**Item 18. Recovery of Erroneously Awarded Compensation.**

(a) Not applicable

(b) Not applicable

**Item 19. Exhibits.**

(a)(1) Not applicable – disclosed with annual report.

(a)(2) Not applicable

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| | |
|:---|:---|
| (a)(3) | [Certifications by the registrant's principal executive officer and principal financial officer, pursuant to Section 302 of the Sarbanes-Oxley Act of 2002 and required by Rule 30a-2 under the Investment Company Act of 1940 are filed herewith.](iv-b_302certifications.htm) |

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(a)(4) Not applicable

(a)(5) Not applicable

(b) [Certifications required by Rule 30a-2(b) under the Act (17 CFR 270.30a-2(b)) are filed herewith.](iv-c_906certifications.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) The
 Caldwell & Orkin Funds, Inc.

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| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp;/s/ Derek Pilecki |
|  | &nbsp;&nbsp;Derek Pilecki, President and Principal Executive Officer |

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Date <u> 12/24/2025</u> <br>

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.

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| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp; /s/ Derek Pilecki |
|  | &nbsp;&nbsp;Derek Pilecki, President and Principal Executive Officer |

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Date <u>12/24/2025 </u> <br>

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| | |
|:---|:---|
| &nbsp;&nbsp;By (Signature and Title) | &nbsp;&nbsp; /s/ Zachary P. Richmond |
|  | &nbsp;&nbsp;Zachary P. Richmond, Treasurer and Principal Financial Officer |

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Date <u> 12/24/2025</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;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;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;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;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;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;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.

---

| | |
|:---|:---|
| 12/24/2025 | /s/ Derek Pilecki |
| Date | Derek Pilecki |
|  | President and Principal Executive Officer |
|  | 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;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;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;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;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;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;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.

---

| | |
|:---|:---|
| 12/24/2025 | /s/ Zachary P. Richmond |
| Date | Zachary P. Richmond |
|  | Treasurer and Principal Financial Officer |
|  | 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, 2025 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:

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

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.

---

| |
|:---|
| 12/24/2025 |
| Date |
| /s/ Derek Pilecki |

---

---

| |
|:---|
| 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, 2025 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:

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

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.

---

| |
|:---|
| 12/24/2025 |
| Date |
| /s/ Zachary P. Richmond |

---

---

| |
|:---|
| 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.