Richard E. and Mary Ann Hurst v. Commissioner

124 T.C. No. 2

UNITED STATES TAX COURT

RICHARD E. AND MARY ANN HURST, Petitioners v.
COMMISSIONER OF INTERNAL REVENUE, Respondent

Docket No. 15792-02. Filed February 3, 2005.

In 1997, as part of their retirement planning, Ps
sold their stock in R Corp. to H Corp. H Corp.
redeemed 90 percent of P-husband’s stock in H Corp.,
and P-husband sold the remainder to his son and two
third parties. Both the redemption and stock sales
provided for payment over 15 years and were secured by
the shares of stock being redeemed or sold. Ps
continued to own H Corp.’s headquarters building, which
they leased back to H Corp. P-wife continued to be an
employee of H Corp. after the redemption, and she and
her husband continued to receive medical insurance
through her employment. All the agreements--stock
purchase and redemption, lease, and employment
contract--were cross-collateralized by P-husband’s H
Corp. stock and contained cross-default provisions.

Held:
1. The sale and redemption of the H Corp. stock
qualifies as a termination redemption under sec.
 - 2 -

302(b)(3), I.R.C. None of the cross-default and cross-
collateralization provisions made P-husband’s post-
transaction interest one “other than an interest as a
creditor.”
2. R’s contention that Ps’ sale of their R Corp.
stock should be analyzed under sec. 304’s rules
governing sales of stock between corporations under
common control must be rejected for lack of evidence
because it was raised only in posttrial briefing and is
a “new matter” rather than a “new argument.”
3. P-wife is a “2-percent shareholder” under
section 1372, I.R.C., because the rules of section 318,
I.R.C., attribute to her the ownership of the H Corp.
stock of both her husband and son during 1997;
accordingly, the H Corp. health insurance premiums are
includible in her income, subject to a deduction of a
percentage of their amount under section 162(l)(1)(B),
I.R.C.

Terry L. Zabel, for petitioners.

Bryan E. Sladek, for respondent.

HOLMES, Judge: Richard Hurst founded and owned Hurst Mecha-

nical, Inc. (HMI), a thriving small business in Michigan that re-

pairs and maintains heating, ventilating, and air conditioning

(HVAC) systems. He bought, with his wife Mary Ann, a much small-

er HVAC company called RHI; and together they also own the

building where HMI has its headquarters.

When the Hursts decided to retire in 1997, they sold RHI to

HMI, sold HMI to a trio of new owners who included their son, and

remained HMI’s landlord. Mary Ann Hurst stayed on as an HMI

employee at a modest salary and with such fringe benefits as

health insurance and a company car.
 - 3 -

The Hursts believe that they arranged these transactions to

enable them to pay tax on their profit from the sale of HMI and

RHI at capital gains rates over a period of fifteen years. The

Commissioner disagrees.

FINDINGS OF FACT

The Hursts were married in 1965, and have two children. Mr.

Hurst got his first job in the HVAC industry during high school,

working as an apprentice in Dearborn. He later earned an associ-

ate’s degree in the field from Ferris State College. After ser-

ving in the military, he moved back to Detroit, and eventually

gained his journeyman’s card from a local union. In 1969, he and

his wife made the difficult decision to move their family away

from Detroit after the unrest of the previous two years, and they

settled in Grand Rapids where he started anew as an employee of a

large mechanical contractor.

In April 1979, the Hursts opened their own HVAC business,

working out of their basement and garage. Mr. Hurst handled the

technical and sales operations while Mrs. Hurst did the bookkeep-

ing and accounting. The business began as a proprietorship, but

in November of that year they incorporated it under Michigan law,

with Mr. Hurst as sole shareholder of the new corporation, named

Hurst Mechanical, Inc. (HMI). In 1989, HMI elected to be taxed

under subchapter S of the Code, and that election has never
 - 4 -

changed.1 The firm grew quickly, and after five years it had

about 15 employees; by 1997, it had 45 employees and over $4

million in annual revenue.

After leaving the Hursts’ home, HMI moved to a converted

gas station, and then to a building in Comstock Park, Michigan.

When the State of Michigan bought the Comstock Park building in

the mid-1990s, the company moved again to Belmont, Michigan, in a

building on Safety Drive. The Hursts bought this building in

their own names and leased it to HMI. In early 1994, the Hursts

bought another HVAC business, Refrigerator Man, Inc., which they

renamed R.H., Inc. (RHI). Each of the Hursts owned half of RHI’s

stock.

In 1996, with HMI doing well and settled into a stable

location, the Hursts began thinking about retirement. Three

employees had become central to the business and were to become

important to their retirement plans. One was Todd Hurst, who had

grown up learning the HVAC trade from his parents. The second

was Thomas Tuori. Tuori was hired in the mid-1980s to help Mary

Ann Hurst manage HMI’s accounting, and by 1997 he was the chief

financial officer of the corporation. The last of the three was

Scott Dixon, brought on in 1996, after Richard Hurst came to

believe that HMI was big enough to need a sales manager. Dixon

1
All references to sections and the Code are to the
Internal Revenue Code in effect for 1997, unless otherwise noted.
 - 5 -

anticipated the potential problems posed by the Hursts’ eventual

retirement so, before joining the firm, he negotiated an

employment contract that included a stock option. His attorney

also negotiated stock option agreements for Tuori and Todd Hurst

at about the same time. These options aimed to protect Dixon and

the others if HMI were sold.

In late 1996, Richard Hurst was contacted by Group

Maintenance American Corporation (GMAC). GMAC was an HVAC

consolidator--a company whose business plan was to buy small HVAC

businesses and try to achieve economies of scale--and it offered

to buy HMI for $2.5 million. Mr. Hurst told Tuori, Dixon, and

Todd about GMAC’s offer, and they themselves confirmed it--only

to learn that GMAC had no interest in keeping them on after a

takeover. Convinced they were ready to run the business, they

approached Mr. Hurst in May 1997 with their own bid to buy his

HMI stock, matching the $2.5 million offered by GMAC. Mr. Hurst

accepted the offer, confident that the young management team he

had put together would provide a secure future for the

corporation he had built up over nearly twenty years.

Everyone involved sought professional advice from lawyers

and accountants who held themselves out as having expertise in

the purchase and sale of family businesses. The general outline

of the deal was soon clear to all. The Hursts would relinquish

control of HMI and RHI to Tuori, Dixon, and Todd Hurst, and
 - 6 -

receive $2.5 million payable over fifteen years. HMI, Inc. would

continue to lease the Safety Drive property from the Hursts. The

proceeds from the sale of the corporations and the rent from the

lease would support the Hursts during their retirement. Mrs.

Hurst would continue to work at HMI as an employee, joining the

firm’s health plan to get coverage for herself and her husband.

Tuori, Dixon, and Todd Hurst would own the company, getting the

job security they would have lacked had HMI been sold.

Everything came together on July 1, 1997: HMI bought 90

percent of its 1000 outstanding shares from Mr. Hurst for a $2

million note. Richard Hurst sold the remaining 100 shares in HMI

to Todd Hurst (51 shares), Dixon (35 shares), and Tuori (14

shares). The new owners each paid $2500 a share, also secured by

promissory notes. HMI bought RHI from the Hursts for a $250,000

note.2 (All these notes, from both HMI and the new owner, had an

interest rate of eight percent and were payable in 60 quarterly

installments.) HMI also signed a new 15-year lease for the

Safety Drive property, with a rent of $8,500 a month, adjusted

for inflation. The lease gave HMI an option to buy the building

from the Hursts, and this became a point of some contention--

described below--after the sale. And, finally, HMI also signed a

2
Trial testimony amply demonstrated that an extra $25,000
loan repayment was mistakenly included in the sale price of RHI,
and the Commissioner now agrees that RHI’s price was $250,000.
 - 7 -

ten-year employment contract with Mrs. Hurst, giving her a small

salary and fringe benefits that included employee health

insurance.

If done right, the deal would have beneficial tax and nontax

effects for the Hursts. From a tax perspective, a stock sale

would give rise to long-term capital gain, taxed at lower rates

than dividends.3 And by taking a 15-year note, rather than a

lump sum, they could qualify for installment treatment under

section 453, probably letting them enjoy a lower effective tax

rate.

There were also nontax reasons for structuring the deal this

way. HMI’s regular bank had no interest in financing the deal,

and the parties thought that a commercial lender would have

wanted a security interest in the corporations’ assets. By

taking a security interest only in the stock, the Hursts were

allowing the buyers more flexibility should they need to encumber

corporate assets to finance the business.

But this meant that they themselves were financing the sale.

And spreading the payments over time meant that they were faced

with a lack of diversification in their assets and a larger risk

3
This was an important consideration to the Hursts--
although HMI was an S corporation at the time of these transac-
tions, and thus subject only to a single tier of tax, secs. 1363,
1366, it had been a C corporation until 1989 and still had
$383,000 in accumulated earnings from those years that had not
been distributed to Mr. Hurst. Without careful planning, these
earnings might end up taxed as dividends under section 1368(c).
 - 8 -

of default. To reduce these risks, the parties agreed to a

complicated series of cross-default and cross-collateralization

provisions, the net result of which was that a default on any one

of the promissory notes or the Safety Drive lease or Mrs. Hurst’s

employment contract would constitute a default on them all.

Since the promissory notes were secured by the HMI and RHI stock

which the Hursts had sold, a default on any of the obligations

would have allowed Mr. Hurst to step in and seize the HMI stock

to satisfy any unpaid debt.

As it turned out, these protective measures were never used,

and the prospect of their use seemed increasingly remote. Under

the management of Todd Hurst, Dixon, and Tuori, HMI boomed. The

company’s revenue increased from approximately $4 million

annually at the time of the sale to over $12 million by 2003.

Not once after the sale did any of the new owners miss a payment

on their notes or the lease.

The Hursts reported the dispositions of both the HMI and RHI

stock on their 1997 tax return as installment sales of long-term

capital assets. The Commissioner disagreed, and recharacterized

these dispositions as producing over $400,000 in dividends and

over $1.8 million in immediately recognized capital gains. In

the resulting notice of deficiency for the Hursts’ 1997 tax year,

he determined that this (and a few much smaller adjustments) led

to a total deficiency of $538,114, and imposed an accuracy-
 - 9 -

related penalty under section 6662 of $107,622.80. The Hursts

were Michigan residents when they filed their petition, and trial

was held in Detroit.

OPINION

Figuring out whether the Hursts or the Commissioner is right

requires some background vocabulary. In tax law, a corporation’s

purchase of its own stock is called a “redemption.” Sec. 317(b).

The Code treats some redemptions as sales under section 302, but

others as a payment of dividends to the extent the corporation

has retained earnings and profits, with any excess as a return of

the shareholder’s basis, and any excess over basis as a capital

gain. Distributions characterized as dividends, return of basis,

or capital gains are commonly called “section 301 distributions,”

after the Code section that sets the general rules in this area.

The rules for redemptions and distributions from S corpora-

tions, which are found in section 1368 and its regulations, add a

layer of complexity, especially when the corporation has accumu-

lated earnings and profits (as both HMI and RHI did). These

rules require computation of an “accumulated adjustments ac-

count,” an account which tracks the accumulation of previously

taxed, but undistributed, earnings of an S corporation. Distri-

butions up to the amount of the accumulated adjustments account

are generally tax free to the extent they do not exceed a share-
 - 10 -

holder’s basis in his stock. (Some of the Hursts’ proceeds from

their sales of their stock benefited from these rules, but that

was not a point of contention in the case.)

For much of the Code’s history (including 1997), noncorpor-

ate sellers usually preferred a redemption to be treated as a

sale because that offered the advantage of taxation at capital

gains rates and the possible recognition of that gain over many

years under section 453’s provisions for installment sales. This

preference led to increasingly elaborate rules for determining

which redemptions qualify as sales and which are treated as divi-

dends or other section 301 distributions. The Code has three

safe harbors: redemptions that are substantially disproportion-

ate with respect to the shareholder, sec. 302(b)(2); redemptions

that terminate a shareholder’s interest, sec. 302(b)(3); and

redemptions of a noncorporate shareholder’s stock in a corpora-

tion that is partially liquidating, sec. 302(b)(4). Each of

these safe harbors comes with its own regulations and case law.

The Code also allows redemption treatment if a taxpayer can

meet the vaguer standard of proving that a particular redemption

is “not essentially equivalent to a dividend.” Sec. 302(b)(1).

The relevant regulation notes that success under this standard

turns “upon the facts and circumstances of each case.” Sec.

1.302-2(b), Income Tax Regs.
 - 11 -

Given the stakes involved, the Hursts and their advisers

tried to steer this deal toward the comparatively well-lit safe

harbor of section 302(b)(3)--the “termination redemption.”

Reaching their destination depended on redeeming the HMI stock in

a way that met the rules defining complete termination of owner-

ship. And one might think that a termination redemption would be

easy to spot, because whether a taxpayer did or didn’t sell all

his stock looks like a simple question to answer. Congress,

however, was concerned that taxpayers would manipulate the rules

to get the tax benefits of a sale without actually cutting their

connection to the management of the redeeming corporation. The

problem seemed especially acute in the case of family-owned

businesses, because such businesses often don’t have strict lines

between the roles of owner, employee, consultant, and director.

The Code addresses this problem by incorporating rules

attributing stock ownership of one person to another (set out in

section 318) in the analysis of transactions governed by section

302. Section 318(a)(1)(A)(ii), which treats stock owned by a

child as owned by his parents, became a particular obstacle to

the Hursts’ navigation of these rules because their son Todd was

to be one of HMI’s new owners. This meant that the note that Mr.

Hurst received from HMI in exchange for 90 percent of his HMI

stock might be treated as a section 301 distribution, because he
 - 12 -

would be treated as if he still owned Todd’s HMI stock--making

his “termination redemption” less than “complete”.

But this would be too harsh a result when there really is a

complete termination both of ownership and control. Thus, Con-

gress provided that if the selling family member elects to keep

no interest in the corporation other than as a creditor for at

least ten years, the Commissioner will ignore the section 318 at-

tribution rules. Sec. 302(c)(2); sec. 1.302-4, Income Tax Regs.4

By far the greatest part of the tax at issue in this case

turns on whether Richard Hurst proved that the sale of his HMI

stock was a termination redemption, specifically whether he kept

an interest “other than an interest as a creditor” in HMI. There

are also two lesser questions--whether the Hursts can treat the

sale of their stock in RHI, the smaller HVAC company, as a sale

or must treat it as a section 301 distribution; and whether the

Hursts owe tax on the health insurance premiums that HMI paid for

Mrs. Hurst.

We examine each in turn.

4
There are other requirements for a termination redemption
to be effective, notably that a taxpayer has to file a timely
election. Sec. 1.302-4, Income Tax Regs. Mr. Hurst filed such
an election for his HMI stock, having received permission from
the District Director to file it late.
 - 13 -

A. Complete Termination of Interest in HMI

The Hursts’ argument is simple--they say that Richard (who

had owned all the HMI stock) walked completely away from the com-

pany, and has no interest in it other than making sure that the

new owners keep current on their notes and rent. The Commission-

er’s argument is more complicated. While acknowledging that each

relationship between the Hursts and their old company--creditor

under the notes, landlord under the lease, employment of a non-

owning family member--passes muster, he argues that the total

number of related obligations resulting from the transaction gave

the Hursts a prohibited interest in the corporation by giving

Richard Hurst a financial stake in the company’s continued

success.

In analyzing whether this holistic view is to prevail, we

look at the different types of ongoing economic benefits that the

Hursts were to receive from HMI: (a) The debt obligations in the

form of promissory notes issued to the Hursts by HMI and the new

owners, (b) their lease of the Safety Drive building to HMI; and

(c) the employment contract between HMI and Mrs. Hurst.

1. Promissory Notes

There were several notes trading hands at the deal’s clos-

ing. One was the $250,000 note issued by HMI to the Hursts for

their RHI stock. The second was the $2 million, 15-year note,

payable in quarterly installments, issued to Mr. Hurst by HMI in
 - 14 -

redemption of 90 percent (900 of 1000) of his HMI shares. Mr.

Hurst also received three 15-year notes payable in quarterly in-

stallments for the remaining 100 HMI shares that he sold to Todd

Hurst, Dixon, and Tuori. All these notes called for periodic

payments of principal and interest on a fixed schedule. Neither

the amount nor the timing of payments was tied to the financial

performance of HMI. Although the notes were subordinate to HMI’s

obligation to its bank, they were not subordinate to general

creditors, nor was the amount or certainty of the payments under

them dependent on HMI’s earnings. See Dunn v. Commissioner, 615

F.2d 578, 582-583 (2d Cir. 1980), affg. 70 T.C. 715, 726-727

(1978); Estate of Lennard v. Commissioner, 61 T.C. 554, 563 & n.7

(1974). All of these contractual arrangements had cross-default

clauses and were secured by the buyers’ stock. This meant that

should any of the notes go into default, Mr. Hurst would have the

right to seize the stock and sell it. The parties agree that the

probable outcome of such a sale would be that Mr. Hurst would

once again be in control of HMI.

Respondent questions the cross-default clauses of the vari-

ous contractual obligations, and interprets them as an effective

retention of control by Mr. Hurst. But in Lynch v. Commissioner,

83 T.C. 597 (1984), revd. on other grounds 801 F.2d 1176 (9th

Cir. 1986), we held that a security interest in redeemed stock

does not constitute a prohibited interest under section 302. We
 - 15 -

noted that “The holding of such a security interest is common in

sales agreements, and * * * not inconsistent with the interest of

a creditor.” Id. at 610; see also Hoffman v. Commissioner, 47

T.C. 218, 232 (1966), affd. 391 F.2d 930 (5th Cir. 1968). Fur-

thermore, at trial, the Hursts offered credible evidence from

their professional advisers that these transactions, including

the grant of a security interest to Mr. Hurst, were consistent

with common practice for seller-financed deals.

2. The Lease

HMI also leased its headquarters on Safety Drive from the

Hursts. As with the notes, the lease called for a fixed rent in

no way conditioned upon the financial performance of HMI. Attor-

ney Ron David, who was intimately familiar with the transaction,

testified convincingly that there was no relationship between the

obligations of the parties and the financial performance of HMI.

The transactional documents admitted into evidence do not indi-

cate otherwise. There is simply no evidence that the payment

terms in the lease between the Hursts and HMI vary from those

that would be reasonable if negotiated between unrelated parties.

And the Hursts point out that the IRS itself has ruled that an

arm’s-length lease allowing a redeeming corporation to use pro-

perty owned by a former owner does not preclude characterization

as a redemption. Rev. Rul. 77-467, 1977-2 C.B. 92.
 - 16 -

The Commissioner nevertheless points to the lease to bolster

his claim that Mr. Hurst kept too much control, noting that in

2003 he was able to persuade the buyers to surrender HMI’s option

to buy the property. Exercising this option would have let HMI

end its rent expense at a time of low mortgage interest rates,

perhaps improving its cashflow--and so might well have been in

the new owners’ interest. But the Hursts paid a price when the

new owners gave it up. Not only did the deal cancel the option,

but it also cut the interest rate on the various promissory notes

owed to the Hursts from eight to six percent. So we think the

Commissioner is wrong in implicitly asserting that the buyers

should have engaged in every behavior possible that would be

adverse to the elder Hursts’ interest, and focus on whether the

elder Hursts kept “a financial stake in the corporation or con-

tinued to control the corporation and benefit by its operations.”

Lynch, 83 T.C. at 604. Ample and entirely credible testimony

showed that the discussions about HMI’s potential purchase of the

Safety Drive location were adversarial: The Hursts as landlords

wanted to keep the rent flowing, and the new owners wanted to

reduce HMI’s cash outlays. Though the Hursts kept their rents,

the new owners did not give up the option gratuitously--making

this a negotiation rather than a collusion.
 - 17 -

3. Employment of Mrs. Hurst

At the same time that HMI redeemed Mr. Hurst’s stock and

signed the lease, it also agreed to a ten-year employment con-

tract with Mrs. Hurst. Under its terms, she was to receive a

salary that rapidly declined to $1000/month and some fringe

benefits--including health insurance, use of an HMI-owned pickup

truck, and free tax preparation.

In deciding whether this was a prohibited interest, the

first thing to note is that Mrs. Hurst did not own any HMI stock.

Thus, she is not a “distributee” unable to have an “interest in

the corporation (including an interest as officer, director, or

employee), other than an interest as a creditor.” Sec.

302(c)(2)(A)(i). The Commissioner is thus forced to argue that

her employment was a “prohibited interest” for Mr. Hurst. And he

does, contending that through her employment Mr. Hurst kept an

ongoing influence in HMI’s corporate affairs. He also argues

that an employee unrelated to the former owner of the business

would not continue to be paid were she to work Mrs. Hurst’s

admittedly minimal schedule. And he asserts that her employment

was a mere ruse to provide Mr. Hurst with his company car and

health benefits, bolstering this argument with proof that the

truck used by Mrs. Hurst was the same one that her husband had

been using when he ran HMI.
 - 18 -

None of this, though, changes the fact that her compensation

and fringe benefits were fixed, and again--like the notes and

lease--not subordinated to HMI’s general creditors, and not sub-

ject to any fluctuation related to HMI’s financial performance.

Her duties, moreover, were various administrative and clerical

tasks--some of the same chores she had been doing at HMI on a

regular basis for many years. And there was no evidence whatso-

ever that Mr. Hurst used his wife in any way as a surrogate for

continuing to manage (or even advise) HMI’s new owners. Cf.

Lynch, 801 F.2d at 1179 (former shareholder himself providing

post-redemption services).

It is, however, undisputed that her employment contract had

much the same cross-default provisions that were part of the

lease and stock transfer agreements. The Commissioner questions

whether, in the ordinary course of business, there was reason to

intertwine substantial corporate obligations with the employment

contract of only one of 45 employees. He points to this special

provision as proof that the parties to this redemption contempla-

ted a continuing involvement greater than that of a mere credi-

tor.

In relying so heavily on the cross-default provisions of the

Hursts’ various agreements, though, the Commissioner ignores the

proof at trial that there was a legitimate creditor’s interest in

the Hursts’ demanding them. They were, after all, parting with a
 - 19 -

substantial asset (the corporations), in return for what was in

essence an IOU from some business associates. Their ability to

enjoy retirement in financial security was fully contingent upon

their receiving payment on the notes, lease, and employment con-

tract. As William Gedris, one of the Hursts’ advisers, credibly

testified, it would not have been logical for Mr. Hurst to relin-

quish shares in a corporation while receiving neither payment nor

security.

The value of that security, however, depended upon the

financial health of the company. Repossessing worthless shares

as security on defaulted notes would have done little to ensure

the Hursts’ retirement. The cross-default provisions were their

canary in the coal mine. If at any point the company failed to

meet any financial obligation to the Hursts, Mr. Hurst would have

the option to retrieve his shares immediately, thus protecting

the value of his security interest instead of worrying about

whether this was the beginning of a downward spiral. This is

perfectly consistent with a creditor’s interest, and there was

credible trial testimony that multiple default triggers are

common in commercial lending.

We find that the cross-default provisions protected the

Hursts’ financial interest as creditors of HMI, for a debt on

which they had received practically no downpayment, and the

collection of which (though not “dependent upon the earnings of
 - 20 -

the corporation” as that phrase is used in section 1.302-4(d),

Income Tax Regs.) was realistically contingent upon HMI’s con-

tinued financial health. The buyers likewise had a motivation to

structure the transaction as they did--their inability to obtain

traditional financing without unduly burdening HMI’s potential

for normal business operations. Even one of the IRS witnesses

showed this understanding of Mr. Hurst’s relationship to the new

owners after the redemption--the revenue agent who conducted the

audit accurately testified that Mr. Hurst was “going to be the

banker and wanted his interests protected.”

The number of legal connections between Mr. Hurst and the

buyers that continued after the deal was signed did not change

their character as permissible security interests. Even looked

at all together, they were in no way contingent upon the finan-

cial performance of the company except in the obvious sense that

all creditors have in their debtors’ solvency.

Moreover, despite the Commissioner’s qualms, we find as a

matter of fact that Mr. Hurst has not participated in any manner

in any corporate activity since the redemptions occurred--not

even a Christmas party or summer picnic. His only dealing with

HMI after the sale was when, as noted above, he dickered with the

buyers over their purchase option on the Safety Drive property.

These facts do not show a continuing proprietary stake or control

of corporate management.
 - 21 -

B. Treatment of the RHI Sale

Analyzing the Hursts’ disposition of their interest in the

smaller HVAC company, RHI, turns out to be more complicated than

analyzing the redemption of their HMI stock. The notice of defi-

ciency was clear in stating that the Commissioner was disallowing

the Hursts’ treatment of the HMI redemption as a sale because

that sale was to a “related party.” And both the Hursts and the

Commissioner understood this to mean that the disposition of Mr.

Hurst’s HMI stock implicated section 302(b)(3). That’s the way

both parties approached trial preparation and then tried the

case. But the notice of deficiency cited no authority in disal-

lowing capital gains treatment for the Hursts’ sale of their RHI

stock, simply including it as a disallowed subitem within the

overall disallowance of Mr. Hurst’s treatment of his HMI stock

sale. The Commissioner’s answer did assert that “both petition-

ers retained prohibited interests, within the meaning of I.R.C.

§ 302(c)(2)(A), in the corporation referred to by petitioners as

‘RH, Inc.’” And though the answer makes no more specific allega-

tion about Mr. Hurst’s alleged “prohibited interest” in RHI, it

does specifically allege that Mrs. Hurst had “an employment con-

tract with that corporation, which is a prohibited interest.”

The issue did not get much attention at trial, because the

stipulated evidence showed that the answer simply got it wrong--

Mrs. Hurst’s employment contract was with HMI, not RHI. And
 - 22 -

neither side showed that either of the elder Hursts had any con-

tinuing involvement in whatever business RHI had left. (Indeed,

the trial left unclear what, if anything, was left of RHI by the

time HMI bought it.)

Relying on section 302 alone to upset the Hursts’ character-

ization of their RHI stock sale under these circumstances seemed

mistaken for another reason: That section governs stock redemp-

tions, and the RHI stock was sold to HMI, not redeemed by RHI.

As already noted, the trial focused almost entirely on HMI, and

the Hursts’ continuing connection to it. Both parties seemed to

assume that if the Hursts won the battle for treating the redemp-

tion of their HMI stock as a sale, they would win as well on RHI.

Now the Commissioner urges us to rely on a different section

of the Code--section 304–-to support his position on RHI. This

section is a more promising ground for him, because it allows him

to treat some stock sales to related corporations as redemptions

under section 302. The problem, however, is that he raised

section 304 for the first time only in his answering brief. The

Hursts object to the introduction of an issue so late in the

proceedings, invoking Aero Rental v. Commissioner, 64 T.C. 331

(1975), and Theatre Concessions v. Commissioner, 29 T.C. 754

(1958). Aero Rental and Theatre Concessions are part of a line

of cases beginning at least with Nash v. Commissioner, 31 T.C.
 - 23 -

569 (1958), in which we have refused to allow a party to raise an

issue for the first time in posttrial briefing.5

To decide whether the Commissioner can do this so late in

the game, we first outline our rules on putting issues in play.

We then analyze section 304 as it might apply here to decide

whether the Commissioner can rely on it.

1. Raising Arguments and Issues After Trial

We begin by noting that we share the Hursts’ dim view of

raising an issue for the first time in a posttrial answering

brief. Numerous procedural safeguards built into the Code and

our own rules are designed to prevent such late-in-the-day maneu-

vering. Section 7522(a) requires the Commissioner to “describe

the basis for” any increase in tax due in the notice of deficien-

cy. After a case in this Court has begun, Rule 142(a) places the

burden of proof on the Commissioner “in respect of any new

5
The Commissioner does argue that the Hursts must have
known that section 304 applied because they both filed waivers of
family attribution for their sale of RHI stock. A close look at
the waiver request shows, however, that it is based on the clear-
ly faulty representation that RHI itself issued the $250,000 note
in redemption of the RHI stock. This appears, then, to be just a
markup of the waiver request filed at the same time by Mr. Hurst
for the actual redemption of his HMI stock. Whether it was filed
out of an abundance of caution by the Hursts’ former adviser or
out of a misunderstanding of the deal, it nowhere mentions the
fact that RHI and HMI might be affected by section 304. And, of
course, the failure of the Commissioner even to raise this point
at trial means that the Hursts didn’t provide any explanation of
their own.
 - 24 -

matter, increases in deficiency, and affirmative defenses,

pleaded in the answer.”

The difficulty for the Hursts is that we do distinguish

between new matters and new theories--“we have held that for

respondent to change the section of the Code on which he relies

does not cause the assertion of the new theory to be new matter

if the section relied on is consistent with the determination

made in the deficiency notice relying on another section of the

Code.” Barton v. Commissioner, T.C. Memo. 1992-118 (citing

Estate of Emerson v. Commissioner, 67 T.C. 612, 620 (1977)),

affd. 993 F.2d 233 (11th Cir. 1993). In short, a “new matter” is

one that reasonably would alter the evidence presented. A “new

theory” is just a new argument about the existing evidence and is

thus allowed.

We therefore describe how section 304 works, how it might

apply to the Hursts’ sale of RHI, and most importantly whether it

would alter the evidence the Hursts might reasonably have wanted

and been able to introduce.

2. Section 304 and the Sale of the RHI Stock

As noted above, the best individual taxpayers can hope for

when disposing of their stock is for it to be treated as a sale

of a capital asset. But this might create an opportunity for a

creative taxpayer in command of two companies to sell his stock

in one to the other, gaining the benefit of sale treatment,
 - 25 -

avoiding any tax on receiving a dividend, all without relinquish-

ing effective ownership. Congress squelches this opportunity

with section 304. It addresses both parent/child situations--the

acquisition by a subsidiary of stock in the parent corporation

that owns it, sec. 304(a)(2); and brother/sister situations-–the

acquisition of one corporation’s stock by another when both are

under common control, sec. 304(a)(1). The Commissioner contends

that the RHI sale to HMI is one of the latter.

What makes this contention look more like a new theory, and

less like a new matter, is the truth that sections 302 and 304

are linked--if section 304 applies to a stock sale, the conse-

quence is that it is treated as a redemption under section 302

and its regulations. And so we begin with the text of section

304(a)(1):

SEC. 304(a). Treatment of Certain Stock Purchases.--

(1) Acquisition by Related Corporation (Other Than
Subsidiary).--For purposes of sections 302 and 303,
if--
(A) one or more persons are in control of each
of two corporations, and

(B) in return for property, one of the
corporations acquires stock in the other
corporation from the person (or persons) in
control,

then * * * such property shall be treated as a
distribution in redemption of the stock of the
corporation acquiring such stock.[6] * * *

6
The Hursts argue that one reason the Commissioner’s argu-
(continued...)
 - 26 -

Section 304(b) then helpfully sets out six paragraphs, ten

subparagraphs, and dozens of clauses and subclauses to explain

section 304(a). If these weren’t clear enough, there are also

seven columns of single-spaced regulations. Secs. 1.304-1

through 1.304-5, Income Tax Regs. The result is a rococo fugue

of tax law.7

To begin de-composing this fugue, we note that section

304(c) and section 1.304-5(b), Income Tax Regs., define “con-

trol,” a term of critical importance in this case. The regula-

tion tells us that in deciding whether section 304(a)(1) applies,

we look to see if the taxpayers involved (1) control both the

issuing and acquiring corporation, (2) transfer stock in the

6
(...continued)
ment should fail is that section 304 was amended effective June
8, 1997 and had a transition provision that exempted binding
deals already reduced to writing even if not yet closed. Howev-
er, the amending language that the Hursts cite did not affect the
first sentence of section 304 quoted above, which has been in the
Code and unchanged for a half century at least. See Internal Re-
venue Code of 1954, ch. 736, sec. 304, 68A Stat 89. It is this
sentence that might affect the tax treatment of the RHI stock
sale.
7
There is a custom of referring to the interplay of section
302 and section 318’s family attribution rules as a “baroque
fugue,” traceable to 1 Bittker & Eustice, Federal Income Taxation
of Corporations and Shareholders, par. 9.04[3] at 9-35 (7th ed.
2002) (so many points and counterpoints as to be a “baroque
fugue”). See also W. Rands, “Corporate Tax: The Agony and the
Ecstasy,” 83 Neb. L. Rev. 39, 69 (2004) (“This provides some
relief in class. We take a five minute break from our work to
discuss whatever a ‘fugue’ is. Usually, most of us do not know,
but occasionally a classical music enthusiast tries to enlighten
us.”). Adding section 304 makes the fugue rococo.
 - 27 -

issuing corporation to the acquiring corporation for property,

and then (3) still control the acquiring corporation thereafter.

We also listen to section 304(c)(3) and section 1.304-5(a), In-

come Tax Regs., which tell us to look at section 318’s attribu-

tion rules to determine who controls what under section 304. See

Gunther v. Commissioner, 92 T.C. 39, 49 n.12 (1989), affd. 909

F.2d 291 (7th Cir. 1990).

In this case, RHI was the “issuing corporation” and HMI was

the “acquiring corporation.” Before the sale, RHI was owned

entirely by Richard and Mary Ann Hurst. Under section

318(a)(1)(A)(i), a taxpayer is considered to own shares of stock

held by his spouse. Thus, we treat HMI and RHI as being under

common control, in that HMI was actually owned by Mr. Hurst and

RHI was constructively owned by Mr. Hurst (since he actually

owned 50 percent and the 50 percent his wife owned is construc-

tively owned by him as well). Moreover, Mrs. Hurst also con-

structively controlled both corporations, in that her husband’s

50-percent interest in RHI was attributed to her (thus putting

her at 100-percent ownership) as was his 100-percent interest in

HMI. Section 304(a)(1)(A) is met.

HMI also acquired the RHI stock in exchange for property,

as the Code makes painfully clear by defining “property” to

include “money”. Sec. 317(a). The accompanying regulation

helpfully clarifies that definition by including as “property” a
 - 28 -

promise to pay money in the future. Sec. 1.317-1, Income Tax

Regs. Thus, section 304(a)(1)(B) is met.

The next issue is whether the Hursts were in “control” of

HMI (the “acquiring corporation”) for section 304 purposes after

the transaction as they were before. Under section

318(a)(1)(A)(ii), a taxpayer constructively owns any stock owned

by his children. Thus, the Hursts are considered to own Todd’s

51-percent interest in HMI. As all three elements of section

1.304-5(b) are met, section 304(a) applies.

Because section 304(a) applies,

determinations as to whether the acquisition
is, by reason of section 302(b), to be
treated as a distribution in part or full
payment in exchange for the stock shall be
made by reference to the stock of the issuing
corporation. * * *

Sec. 304(b)(1).

The consequence of applying section 304 is thus to send us

back to section 302, treating the Hursts’ sale of their RHI stock

to HMI as if it were a redemption by RHI. For the Commissioner,

this deemed redemption analysis under section 302(b) turns on the

uncontested fact that Mrs. Hurst remained an employee of HMI

after the sale. He argues that HMI’s purchase of RHI made RHI

into an HMI subsidiary. Section 1.302-4(c), Income Tax Regs.,

would then govern: “If stock of a subsidiary corporation is

redeemed, section 302(c)(2)(A) shall be applied with reference to

an interest both in such subsidiary corporation and its parent.”
 - 29 -

Thus, despite section 304(b)’s command to treat the RHI sale as a

redemption by RHI, the Commissioner contends that post-sale em-

ployment by either RHI or HMI is a prohibited interest.

So far, so good, for the Commissioner. This analysis looks

as if it is purely legal, and so only a new “theory”. In ana-

lyzing the RHI sale under section 304, it seems, there is no

different evidence that the Hursts could have introduced that

would change the analysis.

But this is where the Commissioner’s failure to raise the

deemed redemption analysis before filing his answering brief be-

gins to look less like a tardy-though-forgivable new theory, and

more like an unforgivable-if-unaccompanied-by-evidence introduc-

tion of a new matter. The Commissioner may well be right that

the Hursts’ sale of their RHI stock couldn’t steer into the safe

harbor of section 302(b)(3). However, there are several other

paragraphs of section 302(b), and if the Commissioner had raised

his section 304 argument earlier, it seems likely that the Hursts

would have counterpunched by exploring whether one of those other

paragraphs would have helped their cause.

Consider, for example, section 302(b)(1), which allows for

exchange treatment of a redemption not essentially equivalent to

a dividend. In order to qualify for exchange treatment under

this provision, a transaction needs to satisfy the “meaningful

reduction * * * [in] proportionate interest” test set out in
 - 30 -

United States v. Davis, 397 U.S. 301, 313 (1970). In this case,

Mrs. Hurst did in fact experience a reduction in her constructive

RHI interest, even after applying section 318’s attribution

rules, because her interest was reduced from 100 percent (her 50-

percent interest plus Mr. Hurst’s 50-percent interest) to 51

percent (her son’s interest in RHI after the deal was done.8

To find that the 49-percent reduction in ownership was

meaningful, we would then have “to examine all the facts and

circumstances to see if the reduction was meaningful for the

purposes of section 302.” Metzger Trust v. Commissioner,

76 T.C. 42, 61 (1981), affd. 693 F.2d 459 (5th Cir. 1982). This

would have allowed the trial to focus upon the practical differ-

ences, if any, which exist between a 51-percent interest and a

100-percent interest in RHI after the sale.

It is true that redemptions in which the 50-percent thresh-

old is not passed will generally be considered essentially equi-

valent to a dividend. Bittker & Eustice, Federal Income Taxation

of Corporations and Shareholders, par. 9.05[3][d] at 9-41 (7th

ed. 2002). Yet an exception exists when a threshold has been

8
Under section 318(a)(2)(C), Todd Hurst’s 51-percent owner-
ship of HMI stock after the sale also makes him constructive ow-
ner of 51 percent of RHI. Section 318(a)(1)(A)(ii) then makes
the elder Hursts constructive owners of 51 percent of RHI even
after they actually sold all of it to HMI. See sec.
318(a)(5)(A).
 - 31 -

passed which alters the practical control of the taxpayer under

State corporate law. Id. ; see also Wright v. United States, 482

F.2d 600, 608-609 (8th Cir. 1973); Patterson Trust v. United

States, 729 F.2d 1089, 1095 (6th Cir. 1984).

Due to the Commissioner’s tardiness in raising the section

304 issue, the parties offered no evidence as to whether the

passage from 100 percent to 51 percent passes any thresholds in

Michigan corporate law that might affect RHI. The record is

similarly bereft of indicators about the rights over RHI held by

Todd Hurst, Tuori, and Dixon. At trial, Tuori and others did

testify that corporate decisions at HMI were made by a majority

vote of himself, Todd Hurst, and Dixon, and that 2-to-1 votes

were regular occurrences. This issue was not fleshed out in the

manner we assume counsel for each party would have, had they

focused upon clarifying the section 304 issue, and we are thus at

a loss to analyze how it would affect a proper section 302(b)(1)

analysis.

At the end of this long digression through sections 304 and

parts of section 302 not raised before or during trial, we need

not reach any firm conclusion on the issue. It is enough to

observe that raising section 304 in an answering brief is in this

case not just making a new argument, but raising a new matter.

The Hursts’ case thus ends up looking like Shea v. Commis-

sioner, 112 T.C. 183 (1999). Here, as in Shea, there is an ob-
 - 32 -

viously applicable law newly relied upon by the Commissioner to

support a portion of the original deficiency. Id. at 197. Here,

as there, ”Respondent failed to offer any evidence that indicated

that respondent considered the application of * * * [that law] in

making his determination.” Id. at 192. We thus view the lack of

evidence on the section 304 question as the Commissioner’s fail-

ure to meet his burden, and we do not rule against the Hursts on

this issue.9

C. The Taxability of Mrs. Hurst’s Medical Benefits

The final issue is the Commissioner’s assertion that the

cost of Mrs. Hurst’s medical insurance paid by HMI is taxable to

her. On this issue, the Commissioner is right. Under section

1372(a), an S corporation (and, remember, HMI elected to be an S

corporation) is treated as a partnership, and any employee who is

a “2-percent shareholder” is treated as a partner when it comes

to deciding whether an employee fringe benefit (like an employ-

er’s share of health insurance premiums) is includible in his

gross income. Amounts paid by a partnership to (or for the bene-

fit of) one of its partners are called “guaranteed payments” un-

9
The Commissioner also contends that the Hursts should have
understood that section 304 was at issue, because “[t]he only
legal theory upon which the respondent could have relied to dis-
allow the installment sale or exchange treatment for the redemp-
tion of the RHI stock is I.R.C. § 304.” Respondent’s Response to
Petitioner’s Motion to Strike A Portion of Respondent’s Brief
par. 2. Our rules do not force taxpayers into such guesswork.
 - 33 -

der section 707(c) of the Code, if they are made without regard

to the partnership’s income. Like a partner, a 2-percent share-

holder is required by section 61(a) to include the value of such

guaranteed payments in his gross income and is not entitled to

exclude them under the Code sections that otherwise allow the

exclusion of employee fringe benefits. See Rev. Rul. 91-26,

1991-1 C.B. 184.

The only question left, then, is whether Mrs. Hurst is a “2-

percent shareholder.” Section 1372(b) defines the term:

SEC. 1372(b). 2-Percent Shareholder Defined.--For
purposes of this section, the term “2-percent sharehol-
der” means any person who owns (or is considered as
owning within the meaning of section 318) on any day
during the taxable year of the S corporation more than
2 percent of the outstanding stock of such corporation
* * *.

And Mrs. Hurst fits within the definition because through

her husband she was a 100-percent shareholder of HMI for

part of the year; through her son, she was a 51-percent

shareholder for the remainder. Owning, even by attribution,

two percent “on any day during the taxable year of the S

corporation” would have sufficed. Thus, the employer’s cost

of her health insurance is clearly includible in her gross

income.

The Hursts are correct, however, that section 1372

gives Mrs. Hurst a deduction for a percentage of the health
 - 34 -

insurance premiums that HMI paid on her behalf. And in

1997, section 162(l)(1)(B) set that percentage at 40.10

To reflect the foregoing and incorporate other

stipulated issues,

Decision will be entered

under Rule 155.

10
The Commissioner also contends that the Hursts are liable
for a penalty under section 6662--either for negligence under
sections 6662(b)(1) and (c) or for substantial understatement un-
der sections 6662(b)(2) and (d). Because we find almost entirely
in the Hursts’ favor, there is no substantial understatement.
The Hursts’ partial victory on the minor issue of calculating
the taxable portion of Mrs. Hurst’s medical insurance premiums
showed no failure in reasonably complying with the Code on that
score, either. The penalty is not sustained. See sec. 6664(c);
sec. 1.6664-4(b)(1), Income Tax Regs.