United States Court of Appeals

For the Eighth Circuit 

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No. 21-3683

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Thomas A. Connelly, in his Capacity as Executor of the Estate of Michael P. 

Connelly, Sr.

 Plaintiff - Appellant

v.

United States of America, Department of Treasury, Internal Revenue Service

 Defendant - Appellee

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Appeal from United States District Court 

for the Eastern District of Missouri - St. Louis

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Submitted: December 14, 2022

Filed: June 2, 2023 

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Before SMITH, Chief Judge, GRUENDER and STRAS, Circuit Judges. 

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GRUENDER, Circuit Judge.

Brothers Michael and Thomas Connelly were the sole shareholders of a 

corporation. The corporation obtained life insurance on each brother so that if one 

died, the corporation could use the proceeds to redeem his shares. When Michael 

died, the Internal Revenue Service assessed taxes on his estate, which included his

stock interest in the corporation. According to the IRS, the corporation’s fair market 
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value includes the life insurance proceeds intended for the stock redemption. 

Michael’s estate argues otherwise and sued for a tax refund. The district court1

agreed with the IRS, and so do we.

I.

Before Michael died, he and Thomas owned Crown C Corporation, a

building-materials company in St. Louis. Michael owned 77.18 percent of the 500 

shares outstanding (385.9 shares); Thomas owned 22.82 percent (114.1 shares). To 

provide for a smooth transition of ownership upon either’s death, the brothers and 

Crown together entered into a stock-purchase agreement. If one brother died, the 

surviving brother had the right to buy his shares. If the surviving brother declined, 

Crown itself had to redeem the shares. In this way, control of the company would 

stay within the family. The brothers always intended that Crown, not the surviving 

brother, would redeem the other’s shares. 

The stock-purchase agreement provided two mechanisms for determining the 

price at which Crown would redeem the shares. The principal mechanism required 

the brothers to execute a new Certificate of Agreed Value at the end of every tax 

year, which set the price per share by “mutual agreement.” If they failed to do so, 

the brothers were supposed to obtain two or more appraisals of fair market value. 

The brothers never executed a Certificate of Agreed Value or obtained appraisals as 

required by the stock-purchase agreement. At any rate, to fund the redemption, 

Crown purchased $3.5 million of life insurance on each brother. 

After Michael died in 2013, Crown received the life insurance proceeds and 

redeemed his shares for $3 million. The actual redemption transaction was part of a 

larger, post-death agreement between Thomas and Michael’s son, Michael Connelly, 

Jr., resolving several estate-administration matters. No appraisals were obtained 

1

The Honorable Stephen R. Clark, Chief Judge, United States District Court

for the Eastern District of Missouri. 
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pursuant to the stock-purchase agreement. Instead, the Connellys declared that they 

had “resolved the issue of the sale price of [Michael’s] stock in as amicable and 

expeditious [a] manner as is possible” and that they “have agreed that the value of 

the stock” was $3 million. That figure effectively valued Crown, based on Michael’s 

77.18 percent share, at $3.89 million. The rest of the proceeds, about $500,000, went 

to fund company operations. 

Thomas is the executor for Michael’s estate. In 2014, the estate filed a tax 

return reporting that Michael’s shares were worth $3 million. To value the shares, 

Thomas relied solely on the redemption payment, rather than treating the life 

insurance proceeds as an asset that increased the corporation’s value and hence the 

value of Michael’s shares. All told, this resulted in an estate tax of about $300,000, 

which was paid.

The IRS audited the estate’s return. It concluded that the estate had 

undervalued Michael’s shares by simply relying on the $3 million redemption 

payment instead of determining the fair market value of Crown, which should 

include the value of the life insurance proceeds. Taking the proceeds into account, 

Crown was worth $3 million more than the estate had determined—about $6.86 

million.2

 So according to the IRS, just before redemption, Michael’s estate actually 

had a 77.18 percent stake in a $6.86 million company—worth about $5.3 million. 

As a result, the IRS sent a notice of deficiency to the estate for $1 million in 

additional tax liability. The estate paid the deficiency and sued for a refund. See 26 

U.S.C. § 7422; 28 U.S.C. § 1346(a)(1). 

2

This figure comes from the IRS’s own valuation of Michael’s interest in 

Crown plus the $3 million in proceeds used for redemption. The IRS independently 

determined that Michael’s shares were worth $2,982,000 exclusive of the proceeds. 

At Michael’s 77.18 percent share, that represents a company value of $3.86 

million—slightly less than the $3.89 million figure arrived at by deeming Michael’s 

shares to be worth $3 million as the redemption transaction effectively did. Because 

the estate does not challenge this sans-proceeds value on appeal, we accept it for our 

purposes. In any event, it does not affect the issue of how to treat the life insurance 

proceeds used for stock redemption. 
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The estate claims that the redemption transaction, made in furtherance of the 

stock-purchase agreement, determined the value of Crown for estate-tax purposes, 

so there is no need to conduct a fair-market-value analysis. Alternatively, the estate 

argues that Crown’s fair market value should not include the life insurance proceeds 

used to redeem Michael’s shares because, although the proceeds were an asset, they 

were immediately offset by a liability—the redemption obligation. In other words, 

the proceeds added nothing to Crown’s value. By contrast, the IRS argues that the 

stock-purchase agreement should be disregarded and that any calculation of Crown’s 

fair market value must account for the proceeds used for redemption. 

The district court granted summary judgment to the IRS. The court first 

concluded that the stock-purchase agreement did not affect the valuation. The court 

then determined that a proper valuation of Crown must include the life insurance 

proceeds used for redemption because they were a significant asset of the company. 

In doing so, the district court declined to follow Estate of Blount v. Commissioner, 

428 F.3d 1338 (11th Cir. 2005), relying instead on the tax code, Treasury 

regulations, and customary valuation principles. The estate appeals. 

II.

A federal tax applies to the transfer of a decedent’s estate, which comprises 

the gross estate minus applicable deductions. 26 U.S.C. §§ 2001, 2051; Comm’r v. 

Est. of Hubert, 520 U.S. 93, 99-100 (1997). A decedent’s gross estate includes “the 

value at the time of his death of all property, real or personal, tangible or intangible, 

wherever situated” in which he had an interest. §§ 2031(a), 2033. Property includes 

stocks. See 26 C.F.R. §§ 20.2031-1, 20.2031-2. For Michael’s gross estate, the only 

issue on appeal is the value of his Crown shares. 

The parties dispute whether Crown’s value, and hence the value of Michael’s 

shares, should include the life insurance proceeds used for redemption. If not, then 

the estate is entitled to a refund. If the proceeds should be included, as the district 

court determined, then the IRS is correct and summary judgment was proper. With 
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this in mind, we review the district court’s grant of summary judgment de novo. 

Westerman v. United States, 718 F.3d 743, 746 (8th Cir. 2013). In refund actions, 

“[t]he [IRS’s] determination of a tax deficiency is presumptively correct, and the 

taxpayer bears the burden of proving that the determination is arbitrary or 

erroneous.” Day v. Comm’r, 975 F.2d 534, 537 (8th Cir. 1992). 

We first consider whether the stock-purchase agreement controls how the 

company should be valued. Finding that it does not, we then consider whether a 

fair-market-value analysis of Crown must include the life insurance proceeds used 

for redemption. It must. 

A.

Generally, the value of any property for tax purposes is determined “without 

regard to any option, agreement, or other right to acquire . . . the property at a price 

less than the fair market value” or to “any other restriction on the right to sell or use 

such property.” 26 U.S.C. § 2703(a). These sorts of agreements are commonly used 

by closely held corporations to keep control among a small group of people. See 3 

James D. Cox & Thomas Lee Hazen, Treatise on the Law of Corporations § 18:13

(3d ed. Dec. 2022 update). Section 2703(a) tells us to ignore these agreements unless 

they meet the criteria in subsection (b). Under § 2703(b), to affect valuation, the 

agreement must (1) be a bona fide business arrangement, (2) not be a device to 

transfer property to members of the decedent’s family for less than full and adequate 

consideration, and (3) have terms that are comparable to other similar arrangements 

entered into in arm’s length transactions. Here, the estate argues that we should look 

to the stock-purchase agreement to value Michael’s shares because it satisfies these

criteria. 

But the estate glosses over an important component missing from the stockpurchase agreement: some fixed or determinable price to which we can look when

valuing Michael’s shares. After all, if § 2703 tells us when we may “regard” 

agreements to acquire stock “at a price less than the fair market value,” we naturally 
-6- 

would expect those agreements to say something about value in a definite or 

calculable way. See Est. of Lauder v. Comm’r, 64 T.C.M. (CCH) 1643, 1656 (1992) 

(“It is axiomatic that the offering price must be fixed and determinable under the 

agreement.”); see also Est. of Amlie v. Comm’r, 91 T.C.M. (CCH) 1017, 1027 (2006) 

(reviewing the comparability of price terms to determine whether the agreement 

satisfied § 2703(b)(3)). Otherwise, why look to the agreement to value the shares? 

Further, the Treasury regulation that clarifies how to value stock subject to a 

buy-sell agreement refers to the price in such agreements and “[t]he effect, if any, 

that is given to the . . . price in determining the value of the securities for estate tax 

purposes.” 26 C.F.R. § 20.2031-2(h). The regulation also states that “[l]ittle weight 

will be accorded a price” in an agreement where the decedent was “free to dispose 

of” the securities at any price during his lifetime. Id. Courts thus recognize that an 

agreement must contain a fixed or determinable price if it is to be considered for 

valuation purposes. Est. of Blount v. Comm’r, 428 F.3d 1338, 1342 (11th Cir. 2005);

Est. of True v. Comm’r, 390 F.3d 1210, 1218 (10th Cir. 2004); Est. of Gloeckner v. 

Comm’r, 152 F.3d 208, 213 (2d Cir. 1998); see also St. Louis Cnty. Bank v. United 

States, 674 F.2d 1207, 1210 (8th Cir. 1982) (describing when restrictive buy-sell 

agreements “may fix the value of property for estate-tax purposes” (emphasis 

added)). Congress enacted § 2703 against the backdrop of 26 C.F.R. § 20.2031-

2(h), which has remained substantially unchanged, and courts have since interpreted 

the two in tandem. See Amlie, 91 T.C.M. (CCH) at 1024 (“[R]egardless of whether 

section 2703 applies to a restrictive agreement, the agreement must satisfy the 

requirements of pre-section-2703 law to control value for Federal estate tax 

purposes.”); Blount, 428 F.3d at 1343 n.4 (“[C]ourts generally agree that the 

limitation in . . . § 2703 should be read in conjunction with the court-created rule.”); 

True, 390 F.3d at 1231 (describing § 2703 as “essentially codif[ying] the rules laid 

out in § 20.2031-2(h)” that had existed before § 2703 was added in 1990). 

We need not resolve the precise contours of what counts as a fixed or 

determinable price because, wherever that line may be, the stock-purchase 

agreement here falls short given that the brothers and Crown ignored the agreement’s 
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pricing mechanisms. It suffices for our purposes to think of a determinable price as 

one arrived at by “formula,” see Gloeckner, 152 F.3d at 213, as by a “fair, objective 

measure,” see Lauder, 64 T.C.M. (CCH) at 1659, or “calculation,” see True, 390 

F.3d at 1213. 

Here, the stock-purchase agreement fixed no price nor prescribed a formula 

for arriving at one. It merely laid out two mechanisms by which the brothers might

agree on a price. One was the Certificate of Agreed Value, which appears to be 

nothing more than price by “mutual agreement”—essentially, an agreement to agree. 

The other was an appraisal process for determining the fair market value of Crown. 

Although this second mechanism seems to carry more objectivity, there is nothing 

in the stock-purchase agreement, aside from minor limitations on valuation factors, 

that fixes or prescribes a formula or measure for determining the price that the 

appraisers will reach. Instead, the agreement required only that the appointed 

appraisers “independently determine and submit” their “appraisal[s] of the fair 

market value of the Company.” The brothers were then supposed to average the 

results or consult a third appraiser as a tiebreaker. None of this was ever done. See 

St. Louis Cnty. Bank, 674 F.2d at 1211 (noting that upon death, the provisions of the 

stock-purchase agreement were not invoked and that post-death conduct may be 

relevant to understanding the nature of the agreement). Thus, “under the 

circumstances of th[is] particular case,” neither price mechanism constituted a fixed 

or determinable price for valuation purposes. See 26 C.F.R. § 20.2031-2(h). If 

anything, the appraisal mechanism calls for a rather ordinary fair-market-value 

analysis, which § 2031 and § 2073(a) essentially require anyway. Nothing therefore 

can be gleaned from the stock-purchase agreement.3

 

3

The estate does not argue that the stock-purchase agreement otherwise 

controls the fair market value of Crown by virtue of its restriction on the transfer of 

shares (i.e., through non-price-related means). Compare § 2703(a)(2), with 

§ 2703(a)(1). And even if we understood the estate to make this argument, we find 

it indistinguishable from the estate’s fair-market-value argument that we address in 

Part II.B below. 
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Thomas tries to get around this problem by directing us to the price fixed by 

the redemption transaction—the $3 million that Crown actually paid for Michael’s 

shares. In his view, this is an appropriate valuation because the redemption 

transaction links back to the stock-purchase agreement and was done pursuant to it. 

We are not convinced. For one, the $3 million price was chosen after Michael’s 

death. See 26 U.S.C. § 2031(a) (requiring that value be determined “at the time of 

[the decedent’s] death”); True, 390 F.3d at 1218 (noting that “the terms of the 

agreement [must be] binding throughout life and death”). And second, the $3 

million price came not from the mechanisms in the stock-purchase agreement but 

rather from Thomas and Michael Connelly, Jr.’s “amicable agreement” resolving 

outstanding estate-administration matters. Thus, Crown’s value must be determined 

“without regard” to the stock-purchase agreement. See § 2703(a). 

B. 

We now consider the fair market value of Michael’s shares. The key question 

is whether the life insurance proceeds received by Crown and intended for 

redemption should be taken into account when determining the corporation’s value

at the time of Michael’s death.

4

 Two principles guide the analysis. The first deals 

with valuing property in general, and the second addresses companies whose stock 

prices cannot be readily determined from an exchange, as is the case with closely 

held corporations. 

4

We focus on this moment in time—after Michael’s death but before his 

shares are redeemed. See Bright’s Est. v. United States, 658 F.2d 999, 1006 (5th Cir. 

1981) (en banc) (“[T]he estate tax is an excise tax on the transfer of property at death 

and accordingly . . . the valuation is to be made as of the moment of death and is to 

be measured by the interest that passes, as contrasted with the interest held by the 

decedent before death or the interest held by the legatee after death.”). Regardless

of the timing, no one argues that the proceeds were ever in doubt. Crown expected 

to receive $3.5 million from the policy, most of which would be used to buy 

Michael’s shares. 
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Generally, the value of property in the gross estate is “the price at which the 

property would change hands between a willing buyer and a willing seller, neither 

being under any compulsion to buy or to sell and both having reasonable knowledge 

of relevant facts.” 26 C.F.R. § 20.2031-1(b); see also United States v. Cartwright, 

411 U.S. 546, 551 (1973) (“The willing buyer-willing seller test of fair market value 

is nearly as old as the federal income, estate, and gifts taxes themselves . . . .”). 

To this end, for closely held corporations, the share value “shall be determined 

by taking into consideration, in addition to all other factors, the value of stock or 

securities of corporations engaged in the same or a similar line of business which are 

listed on an exchange.” 26 U.S.C. § 2031(b). Treasury regulations have interpreted

this as a “fair market value” analysis. 26 C.F.R. § 20.2031-2(a). The fair market 

value depends on the company’s net worth, prospective earning power and dividendpaying capacity, and other relevant factors like “the good will of the business; the 

economic outlook in the particular industry; the company’s position in the industry 

and its management; [and] the degree of control of the business represented by the 

block of stock to be valued.” 26 C.F.R. § 20.2031-2(f)(2); see also Est. of Huntsman 

v. Comm’r, 66 T.C. 861, 876 (1976) (“[W]e . . . determine the fair market value of 

the decedent’s stock . . . by applying the customary principles of valuation . . . .”). 

Setting aside for the moment the life insurance proceeds used to redeem Michael’s 

shares, so far as Crown’s operations, revenue streams, and capital are concerned, we 

know its value—about $3.86 million. See supra n.2. 

But in valuing a closely held corporation, “consideration shall also be given 

to nonoperating assets, including proceeds of life insurance policies payable to or 

for the benefit of the company, to the extent such nonoperating assets have not been 

taken into account in the determination of net worth, prospective earning power and 

dividend-earning capacity.” 26 C.F.R. § 20.2031-2(f)(2). This need to “take[] into 

account” life insurance proceeds appears again in a nearby regulation, 26 C.F.R. 

§ 20.2042-1(c)(6). That regulation clarifies 26 U.S.C. § 2042, which has to do with 

life insurance proceeds that go to beneficiaries other than the decedent’s estate. 

Understanding the relationship between § 2031 (defining the gross estate) and 
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§ 2042, along with their corresponding regulations, helps further illuminate what it 

means to “take[] into account” life insurance proceeds. 

Section 2042 says that the value of a decedent’s gross estate includes life 

insurance proceeds received directly by the estate as well as proceeds received by 

other beneficiaries under insurance policies in which the decedent “possessed at his 

death any of the incidents of ownership.” For example, if Michael obtained a life 

insurance policy for the benefit of Crown, the value of that policy’s proceeds would 

be included in Michael’s gross estate. See § 2042(2). Yet here, Crown obtained the 

policy for its own benefit. 

Now, there might be a plausible argument that under § 2042 Michael

possessed “incidents of ownership” in the life insurance policy through his 

controlling-shareholder status. If that were the case, then § 2042 would require that 

Michael’s gross estate include the proceeds used for his stock redemption. But that 

is not the case. Treasury regulation § 20.2042-1(c)(6) clarifies that a decedent does 

not possess the “incidents of ownership” described in § 2042 merely by virtue of 

being a controlling shareholder in a corporation that owns and benefits from the 

policy. 

Still, although § 2042 does not require that the proceeds be included here, it 

does not exclude them either. We are cautioned to “[s]ee § 20.2031-2(f) for a rule 

providing that the proceeds of certain life insurance policies shall be considered in 

determining the value of the decedent’s stock.” 26 C.F.R. § 20.2042-1(c)(6). Thus, 

although the life insurance proceeds intended for redemption do not directly 

augment Michael’s gross estate by way of § 2042, they may well do so indirectly

through a proper valuation of Crown. Indeed, the $500,000 of proceeds not used to 

redeem shares and which simply went into Crown’s coffers undisputedly increased 

Crown’s value according to the principles in § 2031 and 26 C.F.R. § 20.2031-2(f)(2). 

We must therefore consider the value of the life insurance proceeds intended 

for redemption insofar as they have not already been taken into account in Crown’s 
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valuation and in light of the willing buyer/seller test. In this sense, the parties agree 

that this case presents the same fair-market-value issue as Estate of Blount v. 

Commissioner, 428 F.3d at 1345-46, from the Eleventh Circuit. But they disagree 

on whether Blount was correctly decided. Like here, Blount involved a stockpurchase agreement for a closely held corporation. Although the court referenced 

the requirement in 26 C.F.R. § 20.2031-2(f)(2) that proceeds be “taken into 

account,” it concluded that the life insurance proceeds had been accounted for by 

the redemption obligation, which a willing buyer would consider. 428 F.3d at 1345. 

In balance-sheet terms, the court viewed the life insurance proceeds as an “asset” 

directly offset by the “liability” to redeem shares, yielding zero effect on the 

company’s value.5

 The court summarized its conclusion with an appeal to the 

willing buyer/seller concept: “To suggest that a reasonably competent business 

person, interested in acquiring a company, would ignore a $3 million liability strains 

credulity and defies any sensible construct of fair market value.” Id. at 1346.

Like the estate in Blount, Thomas argues that life insurance proceeds do not 

augment a company’s value where they are offset by a redemption liability. In his 

view, the money is just passing through and a willing buyer and seller would not 

account for it. The IRS counters that this assumption defies common sense and 

customary valuation principles, as reflected in Treasury regulations. 

The IRS has the better argument. Blount’s flaw lies in its premise. An 

obligation to redeem shares is not a liability in the ordinary business sense. See 6A 

Fletcher Cyclopedia of the Law of Corporations § 2859 (Sept. 2022 update) (“The 

redemption of stock is a reduction of surplus, not the satisfaction of a liability.”). 

5

Blount cited favorably the Ninth Circuit’s decision in Estate of Cartwright v. 

Commissioner, 183 F.3d 1034, 1038 (9th Cir. 1999), which employed similar 

reasoning. Like the Eleventh Circuit in Blount, the Ninth Circuit’s analysis was 

limited—one paragraph citing 26 C.F.R. § 20.2031-2(f)(2) and the tax-court 

decision in Estate of Huntsman v. Commissioner, 66 T.C. at 875, which merely 

emphasized that life insurance proceeds are to be considered according to § 20.2031-

2(f)(2). 
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Treating it so “distorts the nature of the ownership interest represented by those 

shares.” See Est. of Blount v. Comm’r, 87 T.C.M. (CCH) 1303, 1319 (2004), aff’d 

in part and rev’d in part, 428 F.3d at 1338. Consider the willing buyer at the time 

of Michael’s death. To own Crown outright, the buyer must obtain all its shares. At 

that point, he could then extinguish the stock-purchase agreement or redeem the 

shares from himself. This is just like moving money from one pocket to another. 

There is no liability to be considered—the buyer controlsthe life insurance proceeds. 

A buyer of Crown would therefore pay up to $6.86 million, having “taken into 

account” the life insurance proceeds, and extinguish or redeem as desired. See 26 

C.F.R. § 20.2031-2(f)(2). On the flip side, a hypothetical willing seller of Crown 

holding all 500 shares would not accept only $3.86 million knowing that the 

company was about to receive $3 million in life insurance proceeds, even if those 

proceeds were intended to redeem a portion of the seller’s own shares. To accept 

$3.86 million would be to ignore, instead of “take[] into account,” the anticipated 

life insurance proceeds. See id. 

To further see the illogic of the estate’s position, consider the resulting 

windfall to Thomas. If we accept the estate’s view and look to Crown’s value 

exclusive of the life insurance proceeds intended for redemption, then upon

Michael’s death, each share was worth $7,720 before redemption.

6

 After 

redemption, Michael’s interest is extinguished, but Thomas still has 114.1 shares 

giving him full control of Crown’s $3.86 million value. Those shares are now worth 

about $33,800 each.7

 Overnight and without any material change to the company, 

Thomas’s shares would have quadrupled in value.8

 This view of the world

6

$3.86 million divided by 500 shares.

7

$3.86 million divided by 114.1 shares.

8

No one has argued that Michael’s death and Thomas’s subsequent sole 

ownership of Crown accounts for such an increase. Cf. Huntsman, 66 T.C. at 879 

(“The decedent was the dominant force in both businesses, and his untimely death 

obviously reduced the value of the stock in the two corporations.”).
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contradicts the estate’s position that the proceeds were offset dollar-by-dollar by a 

“liability.” A true offset would leave the value of Thomas’s shares undisturbed. See 

Cox & Hazen, supra, § 21:2 (“When a corporation purchases its own stock, it has 

depleted its assets by whatever amount of money or property it gave in exchange for 

the stock. There is, however, an increase in the proportional interest of the 

nonselling shareholders in the remaining assets of the corporation.”). In sum, the 

brothers’ arrangement had nothing to do with corporate liabilities. The proceeds 

were simply an asset that increased shareholders’ equity. A fair market value of 

Michael’s shares must account for that reality.

III.

For the foregoing reasons, we affirm the district court’s grant of summary 

judgment to the IRS. 

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