T.C. Memo. 2021-30

UNITED STATES TAX COURT

CAYLOR LAND & DEVELOPMENT, INC., ET AL.,1 Petitioners v.

COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket Nos. 17204-13, 17205-13, Filed March 10, 2021.

17223-13, 19238-13,

23921-13, 23922-13,

23931-13, 11348-14,

17919-14, 17920-14,

17921-14, 17922-14.

1

 We consolidated 12 cases for trial on the issues we analyze in this opinion:

Data Wave Management, Inc., docket number 17205-13; Ibor Corp., docket

number 17223-13; Robert C. Caylor, II and Margo D. Caylor, docket number

19238-13; Robert Caylor Construction Company, docket number 23921-13;

Robert C. Caylor II Exempt Trust, docket number 23922-13; Robert C. Caylor and

Clara E. Caylor, docket number 23931-13; Bantam, LLC, Robert C. Caylor, II

Exempt Trust, Tax Matters Partner, docket number 11348-14; La Playa Caliente,

LLC, Robert C. Caylor II Exempt Trust, Tax Matters Partner, docket number

17919-14; Vistoso LLC, Robert C. Caylor II Exempt Trust, Tax Matters Partner,

docket number 17920-14; Bavispe Limited Partnership, Data Wave Management

Inc., Tax Matters Partner, docket number 17921-14; and Mayfair Crest Limited

Partnership, Ibor Corp., Tax Matters Partner, docket number 17922-14. 

Served 03/10/21
- 2 -

[*2] Derek W. Kaczmarek, David R. Jojola, Giselle C. Alexander, Jay Howard

Zimbler, and John W. Treece, for petitioners.

Michael R. Harrel, Doreen Marie Susi, Wesley J. Wong, and John Robert

Gordon, for respondent.

MEMORANDUM FINDINGS OF FACT AND OPINION

HOLMES, Judge: Bob Caylor and his son Robert Caylor II (Rob) are

entrepreneurs who built a thriving construction business and, in a difficult

industry, have kept the business going for more than a half century. Though it

began as a sole proprietorship, it has since grown into an empire of many separate

subsidiaries and affiliates. And like all businesses, all of the Caylors’ companies

needed insurance. They have long had traditional insurance, which typically cost

the group around $60,000 each year. Beginning in 2007, however, the Caylor

entities increased their insurance bill by taking out policies from a related

microcaptive insurer at a cost of $1.2 million annually. At the same time,

consulting payments between the Caylor entities grew by about $1.2 million. 

These developments were not unrelated. 
- 3 -

[*3] In Avrahami v. Commissioner, 149 T.C. 144 (2017), we found that a

microcaptive didn’t actually provide insurance because it failed to distribute risk

and didn’t act as an insurer commonly would. In Reserve Mech. Corp. v.

Commissioner, T.C. Memo. 2018-86, 115 T.C.M. (CCH) 1475 (2018), appeal

filed, No. 18-9011 (10th Cir. Dec. 20, 2018), we found that a microcaptive didn’t

actually provide insurance because it failed to distribute risk and didn’t act as an

insurer commonly would. Then in Syzygy Ins. Co. v. Commissioner, T.C. Memo.

2019-34, 117 T.C.M. (CCH) 1165 (2019), we found that a microcaptive didn’t

actually provide insurance because it failed to distribute risk and didn’t act as an

insurer commonly would. 

We will break no new ground today. 

FINDINGS OF FACT 

I. Background

This story begins in Arizona back in 1958, when Bob Caylor, with the help

of a loan from his wife Clara, started a small construction company which quickly

grew into Robert Caylor Construction. It started as a sole proprietorship, but Bob

eventually incorporated the business--he officially formed Robert Caylor

Construction Company (Caylor Construction) in 1961. Caylor Construction was a

commercial construction company with expertise as a general building contractor. 
- 4 -

[*4] In an industry known for its volatility, Bob proved to be a steady leader and

avoided overextending in good times. Caylor Construction survived the bad

times, and Bob became recognized in his community as a successful businessman.

Bob and Clara eventually had two children, Rob and Paula Caylor. Rob and

his wife Margo also had two children--Casey and Carly Caylor. Rob began

working for his father in 1973 when he was just nine. Right after graduating from

high school, Rob formed his own construction company--Caylor Land &

Development Company (Caylor Land). Caylor Land focused on commercial and

residential contracting and consulting. With his dad’s helpful advice throughout

the years, Rob managed to build Caylor Land into a successful business.

In the late 1990s Rob bought Caylor Construction. As the companies grew,

they sprouted many other subsidiaries and affiliates--not at all unusual for an

industry where leveraged financing is common and every project carries some risk. 

Here they are:

! RCMC, LLC: An Arizona limited liability company which is solely

owned by the Robert C. Caylor II Exempt Trust. It provides

maintenance and repair services, condominium-association

management services, building-management services, and leasing

services.

! La Playa Caliente, LLC: An Arizona LLC owned equally by Robert

C. Caylor II Exempt Trust and Margo. La Playa develops and owns

real estate. During the years at issue it owned various real estate
- 5 -

properties through a variety of single member LLCs. Those are: Two

East LLC; 260 Pantano, LLC; Lot One on Hacienda, LLC; 6422,

LLC; Next Door, LLC; and 1501 Cherry LLC.

! Bantam, LLC: An Arizona LLC that specializes in governance and

real-estate development issues in Pima County. Its members are

Robert C. Caylor II Exempt Trust with a 47.8% interest, Margo with a

47.8% interest, and Charles Cushman with a 4.4% interest. It owns

two industrial buildings built by Caylor Construction and developed

by Caylor Land.

! Vistoso, LLC: An Arizona LLC whose members are Robert C.

Caylor II Exempt Trust and Margo--each with 50% ownership. 

Vistoso develops and manages office space. It also owns one office

condo building and two condo units built by Caylor Construction.

! 7500 Broadway LLC: An Arizona LLC that owns a single, partly

paved parking lot. Bob and Clara each own half. This property was a

former landfill before Bob bought it in the 1980s.

! Robert C. Caylor II Exempt Trust: An irrevocable trust of which Rob

is the trustee. It owns shares of related operating companies and

interests in some of the Caylor entities--100% of RCMC, 50% of La

Playa and Vistoso, 47.8% of Bantam, 12.5% of Caylor Cotlow, and

0.5% of Bavispe.

! Data Wave Management, Inc.: An Arizona C corporation that

specializes in small businesses and startups. It owns a 1% general

partnership interest in Bavispe and is responsible for managing

Bavispe’s assets. Its only shareholder is Bob.

! Ibor Corp.: An Arizona C corporation owned by Rob and Margo in

equal shares. It owns a 1% general partnership interest in Mayfair

Crest and is responsible for managing the day-to-day operations and

assets of Mayfair.

[*5]
- 6 -

[*6] ! Mayfair Crest Ltd. Partners: A limited partnership that is a funding

mechanism for Caylor Construction that facilitates lines of credit and

debt instruments for the various Caylor entities. Ibor is the general

partner of Mayfair with a 1% interest. Its limited partners are Rob

(44% interest), Margo (44%), Casey A. Caylor GST Trust (9%), and

Carly A. Caylor Exempt Trust (2%). 

! Bavispe, LLP: An Arizona limited partnership that is a real-estate

holding company with a diverse range of investments. Data Wave is

a general partner of Bavispe with a 1% interest. The limited partners

are Rob and Clara (98.5% interest) and Robert C. Caylor II Exempt

Trust (0.5%).

We will collectively refer to all these as the Caylor entities. And we find that Rob

ran this empire primarily through Caylor Construction.

The fortunes of all these Caylor entities were closely tied to the fortune of

Caylor Construction. In 2009, for example, Caylor Land had $1.4 million in gross

receipts, of which $1.2 million was “consulting fees” received from Caylor

Construction. Caylor Land, after it received this “consulting fee,” turned around

and paid “consulting fees” to several of the other subsidiaries. And these

“consulting fees” turned out to be a significant part of the subsidiaries’ revenues:
- 7 -

[*7]

Recipient Total revenues

Consulting fees

received through

Caylor Land

Percentage of

revenue received

through Caylor

Land

7500 Broadway $37,830 $36,180 95.6%

Bantam 95,520 36,180

2

 37.93

 

Bavispe 86,006 42,210 49.1 

Data Wave 42,798 36,180 84.5 

Ibor 144,972 144,720 99.8 

La Playa 1,909,757 156,780 8.2 

Mayfair 198,080 156,780 79.1 

RCMC 352,090 271,695 77.2 

Caylor Trust 204,478 60,300 29.5 

Vistoso 38,980 36,180 92.8 

This revenue breakdown shows that Caylor Construction was the driver of

the success or failure of all the other Caylor entities--in a room full of mice, it was

the 800-pound gorilla. From 2005 to 2008 Caylor Construction reported gross

receipts of $11 million, $15.2 million, $26.1 million, and $20.6 million,

respectively. When the Great Recession hit, Caylor Construction did not escape

2

 Bantam also received consulting fees from RCMC of $41,820 for tax year

2009, which means that it received a total of $78,000 in consulting fees from

related companies.

3

 If one includes the RCMC payment, then 81.66% of Bantam’s came from

related companies.
- 8 -

[*8] unscathed. Its revenues fell in 2009 and 2010, first to $8 million and then to

$6.2 million.

II. The Move to a Microcaptive

4

A. The Pitch

For nearly three decades Caylor Construction bought traditional third-party

commercial property, casualty, and liability insurance through its longtime

insurance broker, Tommy Gee. For the past 15 years Gee had brokered Caylor

Construction’s traditional insurance from the Cincinnati Insurance Co. Caylor

Construction didn’t skimp on this traditional insurance--it had the broadest

policies available in the commercial-insurance marketplace covering:

! commercial property,

! general liability,

! umbrella/excess liability,

! electronic data processing,

! contractors equipment,

4

 A quick vocabulary lesson may be helpful at this point. A “captive

insurance company” is a corporation whose stock is owned by one or a small

number of companies and which handles all or a part of the insurance needs of its

shareholders or their affiliates. Harper Grp. v. Commissioner, 96 T.C. 45, 46 n.3

(1991), aff’d, 979 F.2d 1341 (9th Cir. 1992). A “microcaptive” is a small captive

insurance company. Avrahami v. Commissioner, 149 T.C. 144, 179 (2017). To

be “small”, the captive must take in less than $1.2 million in premiums. Id. 
- 9 -

[*9] ! installation floater,

! commercial auto, and

! terrorism. 

These policies not only insured Caylor Construction, but also other Caylor entities

and Rob’s family:

! Caylor Land Development;

! Bob and Clara Caylor;

! Rob and Margo Caylor;

! Clara Caylor LLC;

! Fidelity National Title Trust No. 10270;

! Robert Caylor DBA Caylor Commercial Developers;

! Robert Caylor II DBA Robert Caylor Investment;

! Caylor Cotlow, LLC;

! Bavispe;

! Mayfair;

! Ibor;

! Caylor Trust;

! 6191 E. Miramar, LLC;

! La Playa;
- 10 -

[*10] ! Data Wave;

! 7500 Broadway;

! Caylor Construction;

! Two East;

! 6422 Speedway;

! Leandro, LLC;

! Lot One on Hacienda;

! Carly Caylor;

! Casey Caylor;

! Casey A. Caylor GST Trust;

! Carly A. Caylor Exempt Trust;

! Laplata Norte, LLC;

! RCMC;

! Next Door;

! 1501 Cherry;

! 260 Pantano;

! Bantam; and

! Vistoso.
- 11 -

[*11] From 2005-14, Caylor Construction paid the following premiums for itself

and all the Caylor entities:

Coverage period Amount

Aug. 1, 2005 to Aug. 1, 2006 $61,608

Aug. 1, 2006 to Aug. 1, 2007 58,800

Aug. 1, 2007 to Aug. 1, 2008 59,917

Aug. 1, 2008 to Aug. 1, 2009 58,121

Aug. 1, 2009 to Aug. 1, 2010 54,898

Aug. 1, 2010 to Aug. 1, 2011 52,269

Aug. 1, 2011 to Aug. 1, 2012 64,330

Aug. 1, 2012 to Aug. 1, 2013 69,830

Aug. 1, 2013 to Aug. 1, 2014 63,254

But this traditional insurance didn’t cover every loss that the Caylor entities

faced over the years. From 1997-2007, the Caylor entities had $500,000 of losses

that were not covered by their traditional insurance--roughly $50,000 a year.

This gap in coverage irritated Rob. In early 2007 an acquaintance

introduced him to the idea of a captive insurance company. Rob, along with his

father and Richard Kennedy, his longtime accountant, went to a lunch presentation

on captive insurance at the Tucson Country Club. This presentation was put on by

Tribeca--an insurance-management company located in Arizona that specialized in
- 12 -

[*12] managing captive insurance companies.

5

 The presentation was a primer on

captive insurance and emphasized microcaptives and their potential tax benefits.

Rob was convinced after the presentation that the Caylor entities could

benefit from such an arrangement--but Kennedy was less convinced, and

presciently thought the pitch for a microcaptive “too good to be true.” Rob asked

Kennedy to look into Tribeca to see if there was anything bad about the company

and to poke around captive insurance generally, to see if it was legitimate from a

tax standpoint. Kennedy made clear that this area was outside of his expertise, but

he searched the internet for information about captive insurance companies and

checked with a friend at the State Board of Accountancy to see if there were any

complaints against Tribeca. He concluded that captive insurance, if done

correctly, had potential. But Kennedy also told Rob that he himself could not

determine if Tribeca’s specific program satisfied the Code’s requirements, and we

specifically find that this meant he told Rob that he was unsure if Tribeca’s

program would be able to deliver on the promised tax benefits. 

Rob also asked Greg Gadarian, his longtime tax and business attorney, to

look into captive insurance. Gadarian had already conducted some research for

5

 In December 2010 Tribeca was purchased by Artex Risk Solutions, Inc. 

Since the company was known as Tribeca for almost all the years at issue, we will

refer to it as Tribeca throughout. 
- 13 -

[*13] other clients, but he also acknowledged that he was no expert in the area. 

After Rob asked him, he read some articles on the subject and talked to another

attorney who was more familiar with this area of law. After this brief inquiry,

Gadarian came to the same conclusion that Kennedy did--that captive insurance

was a legitimate concept, so long as it was “established correctly and operated

correctly.” And also like Kennedy, Gadarian didn’t (or couldn’t) advise Rob on

whether Tribeca’s specific program would satisfy the requirements laid out in the

Code. We also note that Rob never asked Gee, his longtime insurance adviser,

about whether to go forward with a captive and Tribeca.

B. Formation

These general comments from Kennedy and Gadarian were good enough for

Rob, and he decided to go forward in setting up a captive insurance company with

Tribeca as its third-party manager. He began the process by answering a general

questionnaire that Tribeca sent him. He signed an engagement letter with Tribeca

in September 2007. The letter stated that the captive needed to meet certain “risk

shifting” and “risk distribution” tests.

6

 Things moved quickly. Within a month,

6

 To ensure adequate risk distribution, Tribeca required the captives it

managed to participate in a risk pool. Caylor’s captive never participated in this

pool.
- 14 -

[*14] Tribeca prepared a feasability study for Caylor Construction. The study

concluded that Caylor Construction was suitable for a captive insurance company.

The Caylors’ captive insurance company, named Consolidated, Inc., was

incorporated under the laws of Anguilla

7

 and licensed as an Anguilla insurance

company. It was owned by Rob. Tribeca filed the articles of incorporation for

Consolidated on December 20, 2007. On December 21, Consolidated elected

under section 953(d)

8

 to be treated as a domestic U.S. corporation for tax

purposes, as well as an election under section 831(b)(2)(A)(ii) to be taxed solely

on investment income so long as its annual premiums did not exceed $1.2

million--which is what made Consolidated a microcaptive. That same day Caylor

Construction paid Consolidated $1.2 million, which it deducted as an insurance

expense on its 2007 tax return.

9

This was at least a bit odd, since Caylor Construction had not yet completed

any underwriting questionnaires, and perhaps even odder because Consolidated

7

 Anguilla is an island of the British West Indies. See Monahan v.

Commissioner, 109 T.C. 235, 236 (1997).

8

 All section references are to the Internal Revenue Code and regulations in

effect for the years at issue, and all Rule references are to the Tax Court Rules of

Practice and Procedure, unless we say otherwise.

9

 Caylor Construction files its returns on a calendar-year basis.
- 15 -

[*15] had not yet underwritten or issued any policies to any of the Caylor entities. 

The record shows, and we find, that Caylor Construction did eventually fill out an

underwriting questionnaire for 2007 by the end of May 2008. And Caylor

Construction did eventually get policies that covered itself and several other

Caylor entities: 7500 Broadway, Bavispe, Carly A. Caylor Exempt Trust, Casey

A. Caylor GST Trust, Caylor Land, Data Wave, Ibor, La Playa, Mayfair, RCMC,

Caylor Trust, and Caylor Construction. But what really made this first year

remarkable was that the 2007 policies that Consolidated finally got around to

issuing in 2008 were “claims-made” policies, which means that any claim had to

be reported during the applicable policy period (or an extended reporting period of

no more than 60 days). So when Caylor Construction paid $1.2 million at the end

of 2007 to Consolidated--the same amount it would be paying during the years at

issue for a year’s worth of coverage--in reality it was receiving at most 10 days of

coverage and possibly none at all. 

The process became less hurried in 2008. The Caylor entities started to buy

their own coverage from Consolidated, and each entity paid its own premiums. 

But as in 2007 the underwriting process for 2008 did not begin until after the 2008

coverage period had already closed.
- 16 -

[*16] C. Execution

These oddities in the 2007 and 2008 policies are not our focus because the

tax years before us are 2009 and 2010. During both those years the Caylor entities

also carried traditional commercial insurance. From August 2008 to August 2011,

Caylor Construction paid a total of $165,288--or roughly $55,000 per year--for

this traditional insurance. And just as in 2007 and 2008, on paper the Caylor

entities supplemented their insurance through Consolidated in 2009 and 2010. 

1. 2009

Consolidated’s coverage changed slightly in 2009. Rob wanted two

additional entities to get supplemental insurance through Consolidated--Vistoso

and Bantam. He completed the underwriting questionnaires for these two

companies and returned them to Tribeca in March 2009.

But this addition was coupled with a subtraction. The Carly Caylor and

Casey Caylor Trusts were removed from Consolidated’s program in July 2009, on

the advice of the Caylors’ CPA who suggested that the Caylors “not * * * pay

insurance premiums through Casey’s and Carly’s Trust.”

With these changes now in place, 12 Caylor entities paid premiums that

added up to $1.2 million to Consolidated:
- 17 -

[*17] Entity Premium payment to Consolidated

Caylor Construction $179,880

Caylor Land 168,000

7500 Broadway 36,000

Bantam 78,000

Bavispe 42,000

Data Wave 36,000

Ibor 144,000

La Playa 168,000

Mayfair 156,000

RCMC 96,000

Caylor Trust 60,000

Vistoso 36,000

 Total 1,199,880

There was a problem. The Carly and Casey Caylor Trusts had already each

paid $21,000 to Consolidated. After the Caylors’ CPA suggested that the

premiums shouldn’t be paid through these trusts, Paula suggested that the trusts be

“refunded” and their premium be “re[located] * * * amongst the remaining

companies.” And that’s just what happened. Consolidated refunded the premiums

paid by the trusts. 

What protections any of these entities--the trusts or the corporations or the

partnerships--were paying for wasn’t actually known in 2009, since the 2009
- 18 -

[*18] policies, following the pattern of previous years, were not prepared until

2010. Gordon Gotzinger, Tribeca’s director of risk management underwriting,

didn’t sign the declarations until August 2010, and Consolidated didn’t deliver the

policies to Rob until December 2010.

We do find that Consolidated did eventually produce policies for these

entities--even if they were claims-made policies delivered well after the policy

periods. Consolidated, however, wrote policies for only three of the entities:

Caylor Construction, Caylor Land, and RCMC. The nine other entities--Mayfair,

Ibor, La Playa, Caylor Trust, Bavispe, Data Wave, 7500 Broadway, Bantam, and

Vistoso--were named “additional insureds” under RCMC’s policies. Here are the

policies:
- 19 -

[*19] Insured Policy

Caylor Construction

Administrative actions

Legal expense reimbursement

Caylor Land

Administrative actions

Legal expense reimbursement

Loss of key contract

RCMC, et al.

Administrative actions

Cyber liability

Legal expense reimbursement

Loss of key contract

Miscellaneous professional liability

Professional services reimbursement

2. 2010

2010 looked much like 2009. The same Caylor entities paid Consolidated

premiums that totaled $1.2 million. These payments were made throughout 2010. 

Here is the breakdown:

Entity Premium payment to Consolidated

Caylor Construction $179,880

Caylor Land 168,000

7500 Broadway 36,000

Bantam 78,000

Bavispe 42,000
- 20 -

[*20] Data Wave 36,000

Ibor 144,000

La Playa 168,000

Mayfair 156,000

RCMC 96,000

Caylor Trust 60,000

Vistoso 36,000

 Total 1,199,880

These were exactly the same premiums as the Caylor entities had paid in 2009.

And again, as in 2009, the Caylor entities paid these premiums without

knowing what policies they were paying for or the total premium amounts. The

worksheet used to renew the policies wasn’t returned to Tribeca until June 2010. 

Rob didn’t sign and return the coverage acceptance forms to Tribeca until

November 2010. Gotzinger didn’t endorse the declaration pages until late January

2011, and they weren’t delivered to Rob until April 2011. And these were again

policies that covered only claims made before they were delivered.

The policies that were eventually produced were similar to 2009’s:
- 21 -

[*21] Insured Policy

Caylor Construction

Administrative actions

Extended warranty

Legal expense reimbursement

Caylor Land

Administrative actions

Legal expense reimbursement

Loss of key contract

RCMC, et al. 

Administrative actions

Cyber liability

Legal expense reimbursement

Loss of key contract

Miscellaneous professional liability

Professional services reimbursement

D. The Flow of Funds

Another noteworthy aspect of these cases is how money found its way from

Caylor Construction to Consolidated during these years.

1. 2009

The payment of Consolidated’s 2009 premiums began on December 30,

2008 when Caylor Construction paid Caylor Land $1,224,160 for “consulting”. 

Caylor Land’s only workers in 2009 were Rob and Paula, and Carly and Casey--

who at the time were only 11 and 18 years old. These consulting payments were
- 22 -

[*22] made without any contract between Caylor Construction and Caylor Land,

and indeed without any records that described when the consultation took place,

what advice was received, or even what subjects were discussed. When pressed at

trial, Bob described what appears to be a morning routine for him and Rob to have

breakfast together and discuss the business. It was during these conversations that

most of the “consulting” seems to have taken place.

After Caylor Construction sent so much money to Caylor Land for

consulting at the end of 2008, Caylor Land made two payments that totaled

$168,000 to Consolidated in 2009. It then paid another $1.1 million for

“professional-consulting fees”

10

 to the other Caylor entities that were covered

under Consolidated’s program. As these entities got this “consulting” revenue,

they spent it on insurance from Consolidated.

11

 We made a table:

10

 This includes payments of $42,000 to both the Carly and Casey Trusts.

11

 When Consolidated refunded the premiums from the Carly Trust and

Casey Trust, the trusts refunded Caylor Land for the “consulting” payments that

they had received earlier that year.
- 23 -

[*23]

Recipient

Consulting fees

received from

Caylor Land

Amount paid to

Consolidated

Consulting

income as a

percentage of

insurance

7500 Broadway $36,180 $36,000 100.5%

Bantam 36,180 78,000 46.4 

Bavispe 42,210 42,000 100.5 

Data Wave 36,180 36,000 100.5 

Ibor 144,720 144,000 100.5 

La Playa 156,780 168,000 93.3 

Mayfair 156,780 156,000 100.5 

RCMC 271,695 96,000 283.0 

Caylor Trust 60,300 60,000 100.5 

Vistoso 36,180 36,000 100.5 

It is not by chance that the consulting payments match the premiums so

closely. When Rob began making these payments in 2008, he made sure the

consulting payments were slightly more than the premium payments so, as he put

it in an email, “the payins do not match the payouts exactly.” 

2. 2010

The next year was very similar. On December 30, 2009 Caylor

Construction paid Caylor Land $1.7 million for consulting. There were no

consulting agreements between Caylor Construction and Caylor Land, and no
- 24 -

[*24] records of when the consulting took place, what advice was received, or

what subjects were discussed. Caylor Land’s employees were still only Rob,

Paula, and Rob’s now slightly older children.

Caylor Land then paid Consolidated $168,000. It paid other Caylor entities

that were part of Consolidated’s insurance program $1.5 million for consulting. 

As in 2009, these consulting payments made up the bulk of the revenue for many

of these entities. These other entities then paid premiums to Consolidated. Here’s

the breakdown:

Recipient

Total

revenue

Consulting

fees

received

fromCaylor 

Land

Percentage

of total

revenue

from

consulting

Amount paid

to

Consolidated

Consulting

income as

a

percentage

of

insurance

7500

Broadway $37,108 $36,018 97.1% $36,000 100.05%

Bantam 186,723 78,039 41.8 78,000 100.05 

Bavispe 61,004 42,021 68.9 42,000 100.05 

Data 

 Wave 46,542 36,018 77.4 36,000 100.05 

Ibor 145,187 144,072 99.2 144,000 100.05 

La Playa 1,961,962 268,084 13.7 168,000 159.6 

Mayfair 287,260 206,078 71.7 156,000 132.1 

RCMC 555,308 546,048 98.3 96,000 568.8 
- 25 -

[*25]

Caylor 

 Trust 173,528 60,030 34.6 60,000 100.05 

Vistoso 53,523 36,018 67.3 36,000 100.05 

E. Claims Paid

All these premiums, for all these years, from all these Caylor entities began

piling up--from 2007 to 2010, Consolidated collected $4.8 million. It is therefore

interesting to observe that in all that time, Consolidated paid only four claims--two

in 2008 and two in 2009--that together amounted to only $43,000.

12

 And,

inasmuch as these claims were made on claims-made policies that Consolidated

didn’t issue until after the policy years had closed, one might expect there to be

something odd about them. One would be right. Let’s take a look at the claims

from 2009 (the only year before us that had claims filed with Consolidated). The

first claim in 2009 was for $13,000 in legal fees that Caylor Construction incurred

to collect a debt. Tribeca requested additional support for the claim--such as an

invoice or proof of payment--but none was ever submitted. Instead Rob and Paula

in their capacities as Consolidated’s owners overruled the captive managers at

Tribeca and ordered that the claim be paid. Consolidated issued a $13,000 check.

12

 No claims were filed in 2007 or 2010. 
- 26 -

[*26] The second claim was filed by La Playa for several separate losses that

included the settlement of several complaints and some legal fees. Tribeca again

requested additional documentation for these claims--perhaps an invoice or proof

of payment. It again received none. Rob and Paula again simply ordered

Consolidated to pay the claim. We have the $10,000 check in the record. And

both these claims were filed before Consolidated issued the policies under which

they were made--indeed, before the policies were even underwritten.

III. Returns, Audit, and Trial

For both 2009 and 2010, Caylor Construction deducted the payments that it

made to Caylor Land as consulting expenses. All the other entities reported their

payments to Consolidated as a combination of deductible insurance expenses,

legal fees, accounting fees, and management fees.

13

 Consolidated reported itself

as a microcaptive, and therefore did not include the $1.2 million in premiums as

taxable income for either year.

For both 2009 and 2010 Kennedy--who is a licensed CPA in

Arizona--prepared the tax returns for almost all of the Caylor entities. The

taxpayers provided anything that was requested. We specifically find that

13

 Despite this odd reporting by the Caylor entities, Consolidated itself

recorded all these payments as “insurance premiums.”
- 27 -

[*27] Kennedy was unable to advise the Caylors about whether Consolidated was

properly operated as an insurance company. He never provided a tax opinion or

memorandum about the requirements for a microcaptive insurance company to

work under the Code. The Caylors didn’t provide, and Kennedy did not ask for,

any documents to support the large consulting fees between Caylor Construction

and Caylor Land--he simply reported the information that was given to him. He

was unaware that many of the Caylor entities were paying nearly 100% of their

gross receipts from consulting on insurance premiums to Consolidated. 

Though Rob had asked Gadarian to look into captives generally, Gadarian

never provided him any written opinion or memorandum. Gadarian never

reviewed any of the paperwork that created Consolidated or any of the tax returns.

And apart from his general statements about captive insurance, we find it more

likely than not that Gadarian gave no oral advice to Rob about Consolidated.

This microcaptive set off some alarms, and the Commissioner began to

investigate. He eventually issued many notices of deficiency to the Caylors and
- 28 -

[*28] many of the Caylor entities.

14

 He also challenged the deductibility of the

consulting payments from Caylor Construction to Caylor Land.

15

The Commissioner also asserts section 6662(a) accuracy-related penalties

for substantial understatement under section 6662(b)(2) or negligence under

section 6662(b)(1).

We tried these cases in Arizona.16 We are left to decide:

! whether the “consulting payments” made between Caylor

Construction and Caylor Land were ordinary and necessary

businesses expenses;

! whether the payments from the Caylor entities to Consolidated were

“insurance expenses;” and

! whether any penalties are owed.

With our foundation laid, we can get to work.

14

 Though we do note that the Commissioner does not challenge

Consolidated’s own returns in the cases that we tried. Cf. Avrahami, 149 T.C.

at 172; Syzygy, 117 T.C.M. (CCH) at 1171.

15

 In his amended answer the Commissioner does not deny the subsequent

deductions from Caylor Land to the other Caylor entities. Rather, he uses these

deductions as an alternative argument that the payments from Caylor Construction

to Caylor Land are not ordinary business expenses.

16

 The Caylors were and remain Arizonans; the Caylor entities all had their

principal place of business or principal offices in Arizona, so all of the taxpayers

in these cases were in Arizona. Any appeals would presumptively go to the Ninth

Circuit. See sec. 7482(b)(1).
- 29 -

[*29] OPINION

I. Consulting Payments

Section 162 allows the deduction of all ordinary and necessary business

expenses. The cases tell us to be more skeptical about expenses between related

parties. See, e.g., Harwood v. Commissioner, 82 T.C. 239, 258 (1984), aff’d

without published opinion, 786 F.2d 1174 (9th Cir. 1986). The reason is that

“expenses” from one related party to another are more likely to be distributions of

profits, which are not deductible. See Elliotts, Inc. v. Commissioner, 716 F.2d

1241, 1243 (9th Cir. 1983), rev’g and remanding on other grounds T.C. Memo.

1980-282; Home Interiors & Gifts, Inc. v. Commissioner, 73 T.C. 1142, 1156

(1980). Still, it’s entirely possible for one company legitimately to incur or pay

business expenses to a related company. See Chapman v. Commissioner, T.C.

Memo. 2014-82, 107 T.C.M. (CCH) 1433, 1435 (2014). To allay our suspicions,

we look to see if there is any corroborating evidence related to these expenses--

invoices, records, dates, hours worked, or projects worked on. See ASAT, Inc. v.

Commissioner, 108 T.C. 147, 174-75 (1997) (no deduction for consulting fees

where no evidence of how fees are determined, no written contract, no detailed

invoices, and no evidence of what might warrant consulting fees); Fuhrman v.

Commissioner, T.C. Memo. 2011-236, 102 T.C.M. (CCH) 347, 348 (2011);
- 30 -

[*30] Weekend Warrior Trailers, Inc. v. Commissioner, T.C. Memo. 2011-105,

101 T.C.M. (CCH) 1506, 1519-20 (2011) (no deduction of management fees to

related corporation without proof of specific services performed); Kimm v.

Commissioner, T.C. Memo. 2003-215, 86 T.C.M. (CCH) 101, 103 (2003).

The Commissioner first challenges the deductibility of these “consulting”

payments that Caylor Construction made to Caylor Land at the end of 2008 and

2009. The testimony and exhibits we have in the record cause us to find it more

likely than not that this “consulting” consisted of conversations that Rob and his

dad had over breakfast. Neither one could say what this consulting concerned,

what subjects they discussed, or the amount of time they spent talking business

instead of the ordinary subjects fathers and sons talk about. For a father and son to

have a warm and loving relationship that helps sustain and grow the family

business is admirable. But it’s not deductible. 

II. Insurance

Insurance premiums are deductible under section 162(a) as ordinary and

necessary expenses if paid or incurred in connection with a trade or business. Sec.

1.162-1(a), Income Tax Regs. Insurance premiums are also included in income

when received by insurance companies. See sec. 61; Avrahami, 149 T.C. at 174. 

Insurance companies are generally taxed on their income in the same manner as
- 31 -

[*31] other corporations. See sec. 831(a). And that’s what made the $1.2 million

in consulting deductions and premiums so likely to raise the IRS’s bureaucratic

eyebrows--that’s the limit on premiums that an insurer can receive without owing

tax. See secs. 501(c)(15), 831(b). An insurance company with premiums that

don’t exceed $1.2 million for the year can elect under section 831(b) to be taxed

only on its investment income. Sec. 831(b)(1) and (2).17

These rules are more complicated when the insurer and the insureds are

related. This is because while insurance is deductible, amounts set aside in a loss

reserve as a form of self-insurance are not. See, e.g., Harper Grp. v.

Commissioner, 96 T.C. 45, 46 (1991), aff’d, 979 F.2d 1341 (9th Cir. 1992); see

also Steere Tank Lines, Inc. v. United States, 577 F.2d 279, 280 (5th Cir. 1978);

Spring Canyon Coal Co. v. Commissioner, 43 F.2d 78, 80 (10th Cir. 1930). But

neither the Code nor the regulations actually defines “insurance.” Securitas

Holdings, Inc. v. Commissioner, T.C. Memo. 2014-225, 108 T.C.M. (CCH) 490,

494 (2014). As with anything that lacks a codified definition, we look to caselaw. 

The Supreme Court has stated that insurance is a transaction that involves

“an actual ‘insurance risk’” and that “[h]istorically and commonly insurance

17

 We reviewed the history of these provisions in Avrahami, 149 T.C.

at 175-76.
- 32 -

[*32] involves risk-shifting and risk-distributing.” Helvering v. Le Gierse, 312

U.S. 531, 539 (1941). The line between nondeductible self-insurance and

deductible insurance is blurry, and we try to clarify it by looking to four

nonexclusive but rarely supplemented criteria:

! risk-shifting;

! risk-distribution;

! insurance risk; and

! whether an arrangement looks like commonly accepted notions of

insurance.

See Avrahami, 149 T.C. at 177; Rent-A-Center, Inc. v. Commissioner, 142 T.C. 1,

13 (2014); see also R.V.I. Guar. Co. v. Commissioner, 145 T.C. 209, 225 (2015);

Harper Grp., 96 T.C. at 58; AMERCO & Subs. v. Commissioner, 96 T.C. 18, 38

(1991), aff’d 979 F.2d 162 (9th Cir. 1992); Securitas, 108 T.C.M. (CCH) at 494. 

To determine whether Consolidated’s policies were insurance, we will use

the same four-part test that we have in the past. In our three prior microcaptive

cases, we have focused on the elements of risk distribution and “commonly

accepted notions of insurance.” See Avrahami, 149 T.C. at 181-97; Syzygy, 117

T.C.M. (CCH) at 1172-76; Reserve Mech, 115 T.C.M. (CCH) at 1483-90. 

We will do so again here.
- 33 -

[*33] A. Risk Distribution

Risk distribution is one of the common characteristics of insurance

identified by the Supreme Court, see Le Gierse, 312 U.S. at 539, and courts will

find it when an insurer pools a large enough collection of unrelated risks, 

Avrahami, 149 T.C. at 181; see also Rent-A-Center, 142 T.C. at 24. “By assuming

numerous relatively small, independent risks that occur randomly over time, the

insurer smoothes out losses to match more closely its receipt of premiums.” 

Clougherty Packing Co. v. Commissioner, 811 F.2d 1297, 1300 (9th Cir. 1987),

aff’g 84 T.C. 948 (1985). 

In each of our previous microcaptive-insurance cases the captive tried to

show risk distribution by investing in an “insurance pool”--a way to reinsure a

large number of geographically diverse third parties. See, e.g., Avrahami, 149

T.C. at 163. In each case, we found that the “insurance pool” wasn’t actually

insurance so it didn’t suffice to show risk distribution. See id., 149 T.C. at 190;

Syzygy, 117 T.C.M. (CCH) at 1172-74; Reserve, 115 T.C.M (CCH) at 1484-85. 

Tribeca told its clients that they had to participate in such a pool to have adequate

risk distribution. Consolidated nonetheless chose not to.

That’s not the end of this case, however. The other way that microcaptive

insurers in our first three cases tried to show that they met the risk-distribution
- 34 -

[*34] requirement was by issuing policies to its own brother and sister entities. 

See Avrahami, 149 T.C. at 182; Syzygy, 117 T.C.M. (CCH) at 1173; Reserve, 115

T.C.M (CCH) at 1484-85. We asked in those cases: “[W]as there a large enough

pool of unrelated risk?” See, e.g., Avrahami, 149 T.C. at 182. The question is not

solely about the number of brother-sister entities insured, but the number of

independent risk exposures. Id. at 183. This was a problem in all three of those

recent cases. In each we found there wasn’t a large enough pool of unrelated risk

from the policies issued to the related entities. See id. at 184 (seven types of

policies to four entities fell short); Syzygy, 117 T.C.M. (CCH) at 1169 (eight

policies to one entity fell short); Reserve, 115 T.C.M. (CCH) at 1479-80 (eleven

or thirteen policies for three entities fell short). 

The Commissioner argues, relying heavily on his expert Dr. David Babbel,

that Consolidated didn’t have enough independent risks. In Babbel’s opinion, the

risks faced by Consolidated--the 12 independent exposures for administrative

action, 11 independent exposures for loss of key contract, 10 for cyberliability,

and 1 for extended warranty--made for much too small a risk pool. But a low

number of independent risks wasn’t the only reason for Babbel’s opinion. He

observed that all of the risks that Consolidated faced were heavily tied to one

entity--Caylor Construction. This is itself a problem. The strong correlation of
- 35 -

[*35] risk between the smaller Caylor entities and Caylor Construction prevented

Consolidated, in his opinion, from having adequate risk distribution. The

taxpayers disagree and argue that risk distribution can be achieved one of three

ways:

! insuring a number of unrelated risks sufficient to allow the law of

large numbers to predict expected losses;

! having risks of at least 12 affiliated companies, none of which has

liability coverage of less than 5% nor more than 15% of the total risk

insured by the insurance; or

! arranging for at least 30% of the risks assumed by the insurance

company to be those of unrelated parties.

Going in reverse order, Consolidated didn’t assume at least 30% risks from

unrelated parties. Consolidated had zero risks from unrelated parties. This one

fails. 

Next, Consolidated did not insure at least 12 affiliated companies, none of

which had liability coverage for less than 5% nor more than 15% of the total risk

by Consolidated. Even with the inclusion of separate Caylor entities, the risk

insured--as determined by the taxpayers’ own expert--was extremely concentrated

in just two companies, while the rest had only minimal risk. According to the

taxpayers’ own expert, two companies--Caylor Construction and La Playa

Caliente--each had more than 30% of the group’s total risk exposure, while seven
- 36 -

[*36] companies--Caylor Land, RCMC, Ibor, Data Wave, 7500 Broadway,

Bantam, and Vistoso--each had less than 5%. We find the taxpayer’s expert

entirely credible in his explanation of these numbers. It aligns him, however, with

Babbel’s testimony that the high concentration of risk means there isn’t sufficient

risk distribution here. This also fails.

The third way that Caylor argues that Consolidated adequately distributed

risk is the law of large numbers--that Consolidated insures a sufficient number of

unrelated risks to allow the law of large numbers to predict losses. This is not

entirely off base--we stated in Avrahami that independent risk exposure is the key. 

Avrahami, 149 T.C. at 183. But this is called the law of large numbers--not

small numbers or some numbers. Our caselaw demonstrates how very large these

numbers must be. In Harper Group, the captive insured 7,500 customers covering

more than 30,000 different shipments and 6,722 special cargo policies. Harper

Grp., 96 T.C. at 51. This meant more than 260,000 air shipments; 18,000 air

flights; and 40,000 shipments on more than 3,000 ocean voyages were covered. 

Id. In Rent-A-Center, the captive insured three types of risks--workers’

compensation, automobile, and general liability. Rent-A-Center, 142 T.C. at 2. It

insured 14,000 employees; 7,000 vehicles; and 2,600 stores. Id. at 2. And in

R.V.I. Guaranty, the insurance company insured one type of risk, the residual
- 37 -

[*37] value of assets. R.V.I. Guar., 145 T.C. at 212. But even there, the insurance

company issued 951 policies covering 714 different insured parties with more than

754,000 passenger vehicles; more than 2,000 individual real-estate properties; and

more than 1.3 million commercial-equipment assets. Id. at 214.

There is no precise number of independent risks that must exist for risk to

be sufficiently distributed to meet this element--we’re not a legislature or

regulator, and that’s not the way common-law concepts become clearer over time. 

The problem for Consolidated is that it faces a number of independent risks that

are at least a couple orders of magnitude smaller than the captives in cases where

we’ve found sufficient distribution of risk. During the years at issue there were at

most 12 independent exposures for administrative-action and legal-expense

reimbursement; 11 independent exposures for loss of key contracts; 10 for

cyberliability, miscellaneous professional liability, and professional-services

reimbursement; and 1 for extended warranty. We find on the basis of this record

that the law of large numbers doesn’t apply to such small numbers. On this issue

Babbel is the more credible witness. 

We also find in the alternative that the majority of the risks Consolidated

faced weren’t independent risks. During trial, both parties played with the

metaphor of a teeter-totter. Babbel testified that the Caylor entities were all so
- 38 -

[*38] dependent on Caylor Construction that it was like having a bunch of mice on

one side and an 800-pound gorilla on the other with no way for Consolidated to

balance the risk that Caylor Construction carried compared to the other entities.

The taxpayers took exception to the analogy and argued that the insured’s revenue

earned doesn’t correlate to the risk Consolidated needed to distribute.

Tribeca, however, calculated premiums for the Caylor entities based on

revenue, which suggests that revenue is some indicator of the risk Consolidated

was purporting to insure. Even if revenue isn’t the only measure of risk, we do

find as a matter of fact that each of the Caylor entities was highly dependent on

Caylor Construction. Many of the entities received all or most of their revenue

from Caylor Construction. Many had no clients other than Caylor Construction. 

And if something were to happen to Caylor Construction or a policy followed by

Caylor Construction was found to be faulty, it would have a severe effect on all of

the other entities. We also think it important that although the Caylor entities are a

big player in the Tucson real-estate market, the group is almost entirely limited to

that market. This means that there was no geographic diversity or industry

diversity in the entities that Consolidated insured. All the entities in one way or

another were a part of the real-estate industry. And all the entities were in Tucson.
- 39 -

[*39] This lack of diversity also supports our finding that the risks insured by

Consolidated were not sufficiently distributed. 

And absent sufficient risk distribution, what Consolidated was providing

was not insurance.

B. Commonly Accepted Sense

While the absence of risk distribution is enough to demolish this scheme,

AMERCO, 96 T.C. at 40, we will as an alternative ground look to see if what

Consolidated was selling was an arrangement that looks like commonly accepted

notions of insurance, see Avrahami, 149 T.C. at 190-91. There is a hint of

question begging here--we say something’s not insurance because it doesn’t look

enough like something we do say is insurance--but it is one of the four criteria

precedent tells us to look for. And one can view it as simply a command to engage

in analogical reasoning--there is an ordinary public meaning of the word

“insurance” widespread in society that people ascribe to contracts without much

thought. A court can then look at novel arrangements that might or might not look

like those contracts in various ways and pronounce whether their differences with

commonly held notions of insurance are important in any particular case. 

Precedent suggests that we look at:
- 40 -

[*40] ! whether the company was organized, operated, and regulated as an

insurance company;

! whether the insurer was adequately capitalized;

! whether the policies were valid and binding;

! whether the premiums were reasonable and the result of an arm’slength transaction; and

! whether claims were paid. 

See, e.g., Avrahami, 149 T.C. at 191; R.V.I., 145 T.C. at 231. We have also

looked at whether the policies covered risks people typically insure and if there

was a legitimate business reason for buying insurance through a captive. See

Hosp. Corp. of Am. v. Commissioner, T.C. Memo. 1997-482, 74 T.C.M. (CCH)

1020, 1038 (1997).

The Caylors argue that Consolidated is just like every other run-of-the-mill

insurance company. They say it was properly regulated and had adequate

capitalization. It paid its claims when they were filed. It had premiums that were

actuarially determined by a third-party captive-management company and those

premiums were actually paid by the Caylor entities. But the Commissioner isn’t

convinced. He has four main issues with Consolidated--when it issued its policies,

how it calculated the premiums it charged, how it processed claims, and what the

Commissioner says were the sheer exuberant excess of those premiums.
- 41 -

[*41] 1. Organization, Operation, and Regulation 

The parties agree that Consolidated was incorporated in Anguilla and filed a

request there to be regulated as an insurance agency. They disagree a bit about

whether Anguilla ever granted Consolidated’s request and whether Consolidated

also needed to follow Arizona’s insurance regulations. The question of whether

Arizona regulations apply to an alien insurance corporation turns out to be an

especially thorny legal issue. We don’t think either of their disagreements matters

to the outcome, so we will leave them for another day. See LTV Corp. v.

Commissioner, 64 T.C. 589, 595 (1975). 

The more telling question is whether Consolidated operated as an insurance

company. Nancy Harman18 and Babbel both credibly testified that Consolidated

was not operated like a normal insurance company. Harman testified that the

process of pricing policies was “very different” from the process everywhere else

she had worked--no other company backed into the premium amount the way

Consolidated and Tribeca did. And Babble testified that he had never seen a real

insurance company issue policies after the period being insured--a practice that

18

 Harman is an insurance underwriter who has worked in several areas of

insurance--from personal to commercial--and for several companies. She also

worked for Tribeca from 2006 to 2009 as a captive manager. We find her

testimony entirely credible.
- 42 -

[*42] appeared to be standard operating procedure for Consolidated and Tribeca.19

He stated “[t]his isn’t how insurance companies typically operate let alone four

years in a row.”

To answer this question ourselves, we “must look beyond the formalities

and consider the realities of the purported insurance transaction.” Hosp. Corp. of

Am., 74 T.C.M. (CCH) at 1037. The realities do not help Consolidated here. We

find Harman was credible in her testimony that Consolidated’s pricing of its

policies was abnormal. We also find Babbel credible that Consolidated’s

operation was entirely abnormal.

We ourselves find that Consolidated’s handling of claims was abnormal. 

The claims that the Caylors and the Caylor entities made during the years at issue

were handled quite differently from how typical insurance companies respond to

their policy holders. It’s common enough for an insurance company to ask for

19

 Babbel also gave his opinion that the payment of $1.2 million from Caylor

Construction to Consolidated for only 10 days of coverage was not typical in the

insurance industry. We recognize that this monster payment for 10 days of

coverage that was nearly the same as the Caylors paid for a full year’s worth of

coverage did not itself occur in a tax year before us. But we consider facts from

years not before us to make findings for years that are. Sec. 6214(b); see, e.g.,

Chaganti v. Commissioner, T.C. Memo. 2016-222, 112 T.C.M. (CCH) 629, 634

(2016), aff’d per curiam, 745 F. App’x 259 (8th Cir. 2018). This particular fact

shows how much more likely it is that Consolidated is self-insurance, if not just a

tax-avoidance scheme. 
- 43 -

[*43] more information from its client when it receives a claim. And Tribeca on

behalf of Consolidated did do that here; but instead of giving that information, the

policy holders just told Consolidated to pay, and Consolidated obeyed. See

Avrahami, 149 T.C. at 192 (approving claims without support is abnormal). 

Even if Consolidated was organized and regulated as an insurance company,

we find it was not operated like one. 

2. Capitalization

We next look at capitalization. The parties agree that Consolidated met the

minimum capitalization requirements of Anguilla. This is the same as adequate

capitalization. See id. at 193. No issue here.

3. Valid and Binding Policies

In Securitas, we found valid and binding policies when “[e]ach insurance

policy identified the insured, contained an effective period for the policy, specified

what was covered by the policy, stated the premium amount, and was signed by an

authorized representative of the company.” Securitas, 108 T.C.M. (CCH) at 497;

see also Avrahami, 149 T.C. at 194; R.V.I., 145 T.C. at 231.

The “policies” provided by Consolidated are the most glaring evidence it

wasn’t an insurance company. During the years at issue (as well as in 2007 and

2008) Consolidated, with the help of Tribeca, didn’t provide policies for the
- 44 -

[*44] Caylor entities until after the claims periods ended. For 2009, the policies

were not prepared until 2010. The declarations weren’t signed by Gotzinger until

August 2010, and they weren’t delivered to Rob until December 2010. The Caylor

entities paid premiums to Consolidated without knowing the total premiums for

each and without knowing what those policies would be for that year. Two claims

were even paid on policies that had not yet been written. 

Much the same occurred for 2010. Rob didn’t sign and return coverage

acceptance forms to Tribeca until November 2010. Gotzinger didn’t endorse the

declaration page until January 2011, and these policies weren’t delivered to Rob

until April 2011.

Writing and delivering “claims made” insurance policies after the claim

period is, we find, abnormal and is to any reasonable observer just plain silly. 

Insurance protects against the risk of loss. See Steven Plitt et al., 1 Couch on Ins.,

sec. 1.6 n.2 (3d ed. 2020). A policy written after the claims period is being written

after there is no longer a risk of loss, which defeats the whole purpose of

insurance. And the experts back us up on our intuition. As we stated above,

Babbel credibly testified that writing the policies after the claims period is not

normal for an insurance company. See supra p. 42. And Harman testified that the

pricing of policies after the period had closed, while common at Tribeca and
- 45 -

[*45] Consolidated, was abnormal in the insurance industry. We find--in strong

terms--that this is not normal behavior.20

4. Reasonable Premiums 

The next question is whether Consolidated’s premiums were reasonable and

the result of an arm’s-length transaction. See Avrahami, 149 T.C. at 194-95. We

have two issues with the premiums here--one macro and one micro.

Our macro issue is that Consolidated charged, and the Caylor entities paid, a

total of $1.2 million per year in premiums. That’s not by itself a sign that

something isn’t like the commonly accepted notions of insurance. But Rob

testified that this insurance was viewed as additional protection from uncovered

claims in the past. And in the 10 years leading up to Consolidated’s formation, the

Caylor entities had incurred only $500,000 in what the Caylors called uncovered

claims--roughly $50,000 per year. While we don’t think that any premium over

$50,000 per year would be per se unreasonable,21 a premium that is so much

20

 There is one other minor point of abnormality we must point out. The

Caylors never consulted Gee, their longtime insurance adviser, about the policies

they were receiving from Consolidated and Tribeca. If this was truly insurance,

we wonder why the Caylors never even asked Gee what kind of policies they

should obtain to supplement their traditional insurance. 

21

 For example, a company may be willing to pay a slightly higher premium

to fix its costs.
- 46 -

[*46] higher--$1,150,000 higher to be specific--looks unreasonable and thus likely

to be for something other than “insurance” as that term is commonly understood.

22

On the micro side we also take issue with how the premiums were

calculated.

23

 Rather than starting with the Caylor entities’ historical losses--which

credible testimony showed would have been standard practice in the

industry--Tribeca started with the total premium amount the Caylor entities as a

whole wished to pay, and then created and priced policies that would fit within

this limit. We acknowledge that Tribeca may have feared that a ten-year loss

history would not have enough data, but ignoring it completely doesn’t make

sense either. Neither does ignoring new information during all four years

Consolidated provided insurance--Consolidated (through Tribeca) never adjusted

its premiums based on the loss history of the Caylor entities. 

The calculations of the premiums also made little sense. Gotzinger, in

calculating the premiums, started in a normal place--the ISO (Insurance Services

22

 Another minor microabnormality is found in who paid for the insurance. 

Caylor Construction paid the premiums for its traditional insurance that covered

all the entities. But with Consolidated, the covered entities each paid their own

premiums--a departure from what appears to be the longtime standard practice

with its traditional insurance.

23

 We note that the actual underwriter of the policies had died before trial

and left no testimony behind.
- 47 -

[*47] Office) base rate.24 But the calculations soon took a detour to crazy town. 

Several adjustments were made to these base rates which had the effect of raising

the premiums for each policy--which makes sense only as an effort to increase the

total premium to the desired $1.2 million.

The most glaring example of these adjustments was something called a

“captive risk factor” adjustment. Tribeca said this adjustment’s purpose was to

inflate premiums to allow captives to grow in financial strength. It did in fact do

this--fiddling with this factor increased premiums by 300%. But this factor is

completely unknown in the conventional insurance industry. Roberta Garland, an

actuary whose testimony we find credible, criticized the use of this factor. She

stated it is not widely used in the industry. Or perhaps we should find that she

understated this--as far as she knew only Tribeca used this factor. She concluded

that Tribeca’s premiums were excessive. Babbel credibly criticized the use of this

factor as well, arguing that its use is “economically futile” and “contrary to

common insurance industry practice.”

We find that the premiums weren’t actuarially determined, and their

parameters and assumptions were not properly documented.

24

 ISO is an industry data collection and rating agency. ISO base rate

attempts to capture the “pure loss costs” per exposure unit (such as revenue) by

state. 
- 48 -

[*48] 5. Payment of Claims

Finally we look at whether Consolidated paid its claims. The simple answer

is yes. But we already discussed the abnormal way these claims were paid. 

See supra p. 44. 

Does all this add up to “insurance in the commonly accepted sense?” We

find it more likely than not that the answer is “no”. Consolidated may have been

organized and regulated as an insurance company, paid the claims filed against it,

and met the minimal capitalization requirements of Anguilla. But it also

calculated premiums in a fanciful way in entirely unreasonable amounts, issued

claims-made policies after the time to make claims had expired, and paid the few

claims that it did on the say-so of its clients. 

We find that it did not operate like an insurance company.

C. Not Insurance

Because we find that Consolidated failed to distribute risk and was not

selling insurance in the commonly accepted sense, we need not decide whether its

transactions involved insurance risk or risk shifting. See, e.g., Clougherty, 811

F.2d at 1300 n.5. Despite the attempts of Consolidated to make its transactions

look like traditional insurance and take advantage of the apparent loophole at the

intersection of section 831 and captive-insurance caselaw, the premiums paid to
- 49 -

[*49] Consolidated and deducted by the Caylor entities are not “insurance” for

federal tax purposes. See, e.g., Avrahami, 149 T.C. at 197. As in Avrahami, as in

Syzygy, and as in Reserve, we find that the microcaptive didn’t actually provide

insurance because it failed to distribute risk and didn’t act as an insurer commonly

would. 

III. Penalties

Our last issue is whether any of this justifies accuracy-related penalties

under section 6662(a). We now know that if the Commissioner wants penalties,

he himself must have laid the foundation by complying with section 6751. The

parties have settled this issue here with a stipulation that the Commissioner

complied with section 6751(b) in only seven of these cases. 

With that in place, we can put up a framework for the merits. Section

6662(a) imposes a 20% penalty on the portion of an underpayment of tax

attributable to any substantial understatement of income tax, sec. 6662(b)(2), or

negligence or disregard of rules or regulations, sec. 6662(b)(1). An

understatement is substantial if it exceeds the greater of $10 million or “10 percent

of the tax required to be shown on the return for the taxable year (or, if greater,

$10,000).” Sec. 6662(d)(1)(B). Negligence includes any failure to make a
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[*50] reasonable attempt to comply with the provisions of the Code; and disregard

includes any careless, reckless, or intentional disregard. Sec. 6662(c). 

Almost all the taxpayers--as a matter of arithmetic--substantially

understated their tax liabilities.

25

 And we find in the alternative that the taxpayers

were also negligent. Negligence includes failure to keep adequate books and

records. See sec. 6662(c); sec. 1.6662-3(b)(1), Income Tax Regs. It also includes

failure to do what a reasonable and prudent person would do under the

circumstances. See sec. 1.6662-3(b)(1), Income Tax Regs.; Neely v.

Commissioner, 85 T.C. 934, 947 (1985). Negligence is strongly indicated when a

taxpayer fails to reasonably attempt to “ascertain the correctness of a deduction

* * * on a return which would seem to a reasonable and prudent person to be ‘too

good to be true’ under the circumstances.” Sec. 1.6662-3(b)(1)(ii), Income Tax

Regs. 

Rob was pitched the idea of a microcaptive as a “tax planning solution” and

a “tax planning tool.” The presentation he attended stated that this scheme would

provide “a tax deduction of up to $1,200,000 * * * per year.” A sophisticated

businessman like Rob should have seen this as “too good to be true.” Kennedy

25

 The Commissioner concedes there are no substantial understatements for

Caylor Land for 2010 and Data Wave for 2009 and 2010.
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[*51] even told Rob that this scheme seemed “too good to be true.” This impels us

to find that Rob didn’t make reasonable attempts to ensure his and his businesses’

entitlements to these deductions. We do find that Kennedy and Gadarian did some

research into captive insurance for Rob, and we do find that both told Rob that a

microcaptive insurance company is a legitimate concept. They’re right about that. 

But they’re also right that it’s a legitimate concept only if “established correctly

and operated correctly.” Neither advised Rob that this microcaptive was

established and operated correctly. And other than Tribeca--which is unable to

offer an unbiased opinion--Rob never investigated if this scheme was operated

correctly. Rob didn’t even follow Tribeca’s advice--which was to invest in the

insurance pool to ensure risk distribution--which itself is unreasonable. And apart

from the deductions of Consolidated’s premiums, Caylor Construction failed to

keep adequate records of its deductions for “consulting” payments. Those were

negligent too. See sec. 6662(c). 

The Caylors try to shore up this position with section 6664(c)--the

reasonable-cause-and-good-faith defense. See sec. 1.6664-4(a), Income Tax Regs. 

We make our determinations about this defense on a case-by-case basis. Sec.

1.6664-4(b), Income Tax Regs. And here we look to see if it applies to either the

consulting payments or the microcaptive scheme. The Caylors argue that they
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[*52] relied on professionals to advise them on how to report these items on their

returns. The Caylors argue that they can establish this defense through the advice

of Gadarian and Kennedy.

We must first determine if these parties gave the Caylor entities any

“advice”. Advice is “any communication * * * setting forth the analysis or

conclusion of a person * * * provided to (or for the benefit of) the taxpayer and on

which the taxpayer relies.” Sec. 1.6664-4(c)(2), Income Tax Regs. 

We specifically find that the Caylor entities received no advice from

Gadarian or Kennedy regarding Consolidated or its insurance scheme. Gadarian

credibly testified that he never offered any advice about the organization and

operation of Consolidated. Kennedy credibly testified that he never offered any

advice about the organization or operation of Consolidated. This finding is

different from those we made in our other microcaptive cases. In Avrahami, 149

T.C. at 207, the taxpayers received actual advice from a tax professional whom

they relied on in good faith. In Syzygy, 117 T.C.M. (CCH) at 1177, the taxpayers

again received actual advice from a tax professional that they relied on in good

faith. The Caylor entities can, in contrast, not rely on advice that was not given.

We find that they had no reasonable cause and did not take their position in good

faith.
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[*53] Caylor Construction also cannot shelter in place behind section 6664(c) for

the consulting payments. Again, the taxpayers argue that Kennedy prepared their

returns and therefore the defense applies. Employing a tax return preparer,

however, doesn’t allow taxpayers to avoid penalties. Neonatology Assocs., P.A.

v. Commissioner, 115 T.C. 43, 100 (2000), aff’d, 299 F.3d 221 (3d Cir. 2002). 

Kennedy simply copied information handed to him on a general ledger onto a tax

return. Kennedy and the Caylors never discussed these payments, which means

the Caylors did not get advice or a professional’s judgment that they could have

reasonably relied upon. See Flume v. Commissioner, T.C. Memo. 2020-80, 119

T.C.M. (CCH) 1545 (2020); Yapp v. Commissioner, T.C. Memo. 2018-147, 116

T.C.M. (CCH) 270 (2018), aff’d, 818 F. App’x 743 (9th Cir. 2020). 

Penalties apply across the board. There will be some calculations needed

from the parties, and because this involves some TEFRA cases, 

Appropriate orders will be issued.