
Vol. 76, No. 3, March 
2003
Tax Deductions for Settlements
with Government Agencies
Depending on the circumstance, companies that 
pay settlements to government agencies may be eligible for a tax 
deduction. Learn what circumstances may lead to a deduction and the 
attorney's role in drafting settlements with the tax issues in mind.
 by Douglas H. Frazer & Karen M. Schapiro
 
by Douglas H. Frazer & Karen M. Schapiro
The Wall Street Journal recently reported that the slew of 
companies caught in chicanery might soften the resultant financial 
impact by getting huge tax breaks from Uncle Sam. "Corporations that pay 
large sums to atone for their sins," said the paper, "usually can write 
off the money on their tax returns, substantially softening the 
financial blow.... Even settlements with government regulators can be 
deducted in many circumstances."1
But what are those circumstances? This article explores the issue of 
the deductibility of settlements with government agencies and the 
attorney's role in drafting settlements with the tax issues in mind. The 
article also addresses the related questions of timing: whether it 
matters that a proceeding is pending or whether a court has ordered or 
confirmed a settlement.2
The Legal Authority for the Deduction
The principal federal code provision authorizing the deductibility of 
settlement payments to government agencies is 26 U.S.C. § 162 
(1986). Section 162(a) allows a deduction of "all the ordinary and 
necessary expenses paid or incurred during the taxable year in carrying 
on any trade or business...." Settlement payments most often are 
characterized in this way. The principle, however, contains an important 
limitation. Under section 162(f), a deduction is disallowed for a "fine 
or similar penalty paid to a government for the violation of any 
law."
Alternatively, deductions for settlement payments to government 
agencies could fall under 26 U.S.C. § 165 (losses on transactions 
entered into for profit). Unlike section 162, however, section 165 does 
not have a parallel limitation that disallows a deduction for a fine or 
similar penalty paid to a government for the violation of any law.
Allowance of the Deduction: The IRS Position
The Internal Revenue Service most recently addressed the issue of the 
deductibility of settlement payments to the government in Field Service 
Advice (FSA) 2002-10011. The FSA involved a taxpayer that had pleaded 
guilty to a Sherman Antitrust Act violation in connection with a Defense 
Department contract for producing image converter tubes. Section 162(f) 
clearly barred the deduction of the criminal fine. The government, 
however, also believed it could recover civil damages under the Lanham 
Trademark Act from the company for filing a false claim, breach of 
contract or warranty, fraudulent or negligent misrepresentation, unjust 
enrichment, or payment by mistake. The taxpayer and the government 
entered into a financial settlement of the claims. The FSA concerned the 
deductibility of a payment under that settlement.
A civil penalty, explained the FSA, "even if it is labeled a penalty, 
may be deductible if it is imposed to encourage compliance with the law 
or as a remedial measure to compensate the party." There is no deduction 
for penalties, however, "imposed for the purpose of enforcing the law or 
as punishment for violation of the law."
Therefore, the determination of the character of a given payment 
involves an interpretation of the statute giving rise to the potential 
or actual litigation (the "origin of the claim") and the specific facts 
of the settlement itself. This is particularly true when a statute 
serves both punitive and compensatory purposes. In such a situation, 
said the FSA, it may be helpful to compare "the payment amount with the 
actual damages caused by the conduct at issue. If a payment exceeds the 
amount needed to compensate the victim, or if it is in addition to a 
separate compensatory payment, it can often be inferred that the payment 
had a punitive purpose."
The potential claims discharged by the settlement included claims 
under the Lanham Trademark Act, which recognizes both compensatory and 
punitive remedies. Section 35(a) of the Act provides that any recovery 
under that part of the Act "shall constitute compensation and not a 
penalty."3 Section 35(b) of the act, on the 
other hand, provides for monetary recovery in the amount of three times 
the defendant's profits or damages, whichever is greater.
The FSA noted that "it is possible for payments pursuant to section 
35(b) of the Lanham Trademark Act to be covered by section 162(f)." 
Thus, the FSA suggested that an attempt be made to ascertain "the intent 
of the parties as to what purpose the payment was designed to serve." 
The FSA observed that "the fact [that] the settlement amount is 
significantly larger than the total contract amount suggests that some 
portion of the settlement payment is likely punitive and subject to 
section 162(f)."
The Deduction in Practice: Case Studies
Government Contract Settlements. The deductibility 
issue frequently arises in government contract litigation settlements. A 
good illustration of this is Talley Industries Inc. v. 
Commissioner.4
A Talley subsidiary, Stencel Aerow Engineering Co., had charged 
certain costs to the wrong government contracts. Talley and the federal 
government settled the case for $2.5 million.
Talley tried to deduct the full settlement amount. The IRS denied the 
deduction in part. The IRS argued that $940,000 of the total was a 
payment of double damages under the Federal Contracts Act and therefore 
was a nondeductible payment of a "fine or similar penalty" under section 
162(f). Talley, on the other hand, contended that the $940,000 was 
intended to compensate the government for any unknown losses. The tax 
court found for the government. Talley appealed.5
The Ninth Circuit Court of Appeals observed that "[i]f the $940,000 
represents compensation to the government for its losses, the sum is 
deductible. If, however, the $940,000 represents a payment of double 
damages, it may not be deductible. If the $940,000 represents a payment 
of double damages, a further genuine issue of fact exists as to whether 
the parties intended the payment to compensate the government for its 
losses (deductible) or to punish or deter Talley and Stencel 
(nondeductible)." Having framed the issue, the court remanded the case 
for a determination of the purpose of the $940,000 payment - and thus 
its deductibility.
On remand, the tax court noted that because the settlement agreement 
did not evidence an intention by the parties that the $940,000 be 
compensatory, the burden of proof was on Talley to establish that it 
was. The company failed to carry that burden. Consequently, the tax 
court disallowed the deduction for the $940,000 portion of the 
settlement.
Environmental Contamination Settlements. Cases 
involving government contracts are not the only situations in which 
deductions may be denied for amounts paid as the result of actual or 
potential litigation. Environmental contamination actions also raise 
this issue.
In Allied-Signal Inc. v. Commissioner,6 a divided court affirmed the tax court's denial of 
any deduction for the $8 million that Allied-Signal paid to an endowment 
set up to eradicate Kepone, a highly toxic chemical pesticide. The 
court, echoing the trial judge's opinion, concluded that the $8 million 
was paid "with the virtual guaranty that the district court would reduce 
the criminal fine by at least that amount."7 
Thus, "the payment was for punishment and deterrence of environmental 
crimes."8
The court found that the parties carefully crafted the transaction so 
that part of the payments would remain in Virginia, where the endowment 
was expected to carry out its activity. "This transaction," concluded 
the court, "did indeed take Allied out of the literal language of 
section 162(f) and provided Allied an arguable basis for claiming an 
ordinary and necessary business expense deduction."9 That, however, was not enough. The court held that 
the payment was in the nature of a criminal fine diverted from the U.S. 
Treasury to the endowment and was thus nondeductible.10
The dissent conceded that the $8 million payment to the endowment 
"was not made from the goodness of Allied-Signal's heart, nor out of an 
overwhelming humanitarian concern, nor from some ecological passion for 
the environment." The payment was made in lieu of a fine and with the 
expectation that it would not be allowed as a deduction if the $8 
million were a fine paid to the government. "Allied's argument to the 
contrary is ridiculous." Nevertheless, concluded the dissent, section 
162(f) applies only if the payment is made to a government. "I cannot 
contort the plain language of section 162(f) that the payment must be 
'to a government,' to arrive at a result that, were I a legislator, I 
would intend. I am not impressed with the arguments about what Congress 
intended to say, because what they did say is clear and 
unambiguous."11
In light of the dissent, Allied-Signal's settlement technique likely 
will be attempted in other circuits.
Colt Industries Inc. v. United States12 also involved the environment, but with civil 
rather than criminal penalties at issue and with the payments going to 
government-operated clean-up funds. Through a subsidiary, Crucible, Colt 
Industries received EPA notices of violations of the Clean Air Act. 
Ultimately, the EPA sought both an injunction and the imposition of 
civil penalties for violations of both the Clean Air Act and the Clean 
Water Act. To settle this, Crucible and the EPA entered into a consent 
agreement. Part of the consent agreement required Crucible to pay $1.6 
million to the Pennsylvania Clean Air and Clean Water funds administered 
by the Pennsylvania Department of Environmental Resources. In turn, Colt 
deducted the payments on its consolidated corporate tax return.
The IRS disallowed the $1.6 million deduction. On appeal, Colt argued 
that section 162(f) "only bars deduction of those civil penalties that 
serve a punitive or criminal purpose." According to Colt, the EPA 
penalties did neither.
The court declined to address the merits of this position. Rather, 
the court found against Colt on the basis that its position was 
administratively impractical. Accepting Colt's interpretation, stated 
the court, would require an analysis of the purpose of each penalty at 
issue "to ascertain whether the payment is barred from deduction." The 
court decided it did not want to get involved with such an inquiry. "The 
role of the judiciary in cases of this sort begins and ends with 
assurance that the Commissioner's regulations fall within his authority 
to implement the congressional mandate in some reasonable manner."
A similarly situated party may want to try again. Simply labeling 
something a penalty does not necessarily make it so. The IRS's recent 
FSA makes this point explicitly.
Colt also argued that the penalty should be deductible 
because it fit within the "compensatory damages" exception set forth in 
Treas. Reg. § 1.162-21(b)(2). In Colt's view, the $1.6 million it 
paid was intended to reflect the economic benefit Crucible had derived 
from noncompliance with the pollution control law.
| 
 
|  |  |  
| Frazer | Schapiro |  Douglas H. Frazer, Northwestern 1985, and 
Karen M. Schapiro, Northwestern 1985, are shareholders 
with Frazer & Schapiro S.C., Milwaukee. 
 | 
The court, however, had a different understanding of compensatory 
damages. It viewed the compensatory damages as being limited to an 
amount paid to a victim to make the victim whole. "Colt," said the 
court, "does not explain how penalties designed to return Crucible to 
the status quo ante compensate the government.... Colt's own argument 
confirms that this was not the purpose of the penalty it paid."
In addition, stated the court, neither the Clean Air Act nor the 
Clean Water Act authorizes the EPA to seek compensatory damages.13
Settlements of Section 165 Losses on For-profit 
Transactions. While section 162(f) controls deductions claimed 
under section 162, a somewhat different set of rules exists as to 
deductions claimed under other sections, such as section 165 (losses on 
transactions entered into for profit). The question is whether public 
policy considerations come into play as to deductions under other 
sections.
Before 1969, the courts had created a "public policy" doctrine 
disallowing a deduction if it frustrated defined national or state 
policies. Section 162(f) codified that area of the law. "It was designed 
to narrow and make more specific the situations in which fines and 
penalties would be nondeductible by implicitly acknowledging that some 
fines and penalties are really more user fees than they are law 
enforcement tools. While that eliminated the public policy doctrine, as 
such, being applicable for section 162 deductions, the codification had 
no direct impact on deductions falling within other sections."14
In Stephens v. Commissioner,15 
the taxpayer was convicted of defrauding the Raytheon Company by 
conspiring with Raytheon personnel and others to overcharge on shipments 
of prefabricated housing to Saudi Arabia. The trial court sentenced the 
taxpayer to either probation or prison, depending on whether the 
taxpayer made restitution to Raytheon.
Stephens had placed part of the proceeds from the crime in an annuity 
account in a Bermuda bank. Stephens allowed $530,000 of the funds in the 
Bermuda account to be applied as partial restitution of the amounts owed 
to Raytheon.
The tax question before the court was the deductibility of that 
$530,000 in the year of repayment. The tax court held that the deduction 
was not properly claimed as a section 162 deduction. It was not an 
ordinary and necessary business expense. Rather, if there were to be a 
deduction, it would be for a loss incurred in a transaction entered into 
for profit under section 165(c)(2).
Because the deduction was not under section 162, then section 162(f) 
would not, by its terms, be applicable. "However," stated the tax court, 
"it does not follow that the standards, which have been established for 
the application of section 162(f) to payments which would otherwise be 
allowable under section 162(a), should not be utilized to determine 
whether a taxpayer should be denied a deduction for a payment which 
might otherwise be allowable under section 165(c)(2)."
The court concluded that at a minimum, "the considerations involved 
in applying section 162(f) extend to the determination of deductibility 
under section 165(c)(2)." Stephens' $530,000 payment as the result of 
the criminal conviction was a probation condition and was in lieu of an 
additional prison term. "That the payment had the effect of reimbursing 
Raytheon for all or part of its loss and, therefore, had a civil aspect, 
does not detract from this overriding fact." The court saw the 
restitution payments as a "similar penalty." The court thus incorporated 
the animating principles of section 162(f) into section 165 and denied 
any deduction. The Second Circuit disagreed with the tax court's 
conclusion. Where the tax court saw the restitution as a trade-off for a 
lighter punishment, the appeals court saw the heavier punishment that 
would be incurred if restitution were not made as a way of assuring that 
Stephens made the restitution. Compensatory payments, which are 
deductible, return the parties to the position they were in; the 
payments that are nondeductible are those imposed to serve a law 
enforcement purpose. Stephens' payments to Raytheon looked compensatory 
to the appeals court, and thus deductible.
The Second Circuit also did not think that allowing the deduction 
would frustrate public policy. Interestingly, the reviewing court agreed 
with the tax court as to the relevance of section 162(f) to deductions 
under other sections, such as section 165. "Congress can hardly be 
considered to have intended to create a scheme where a payment would not 
pass muster under section 162(f), but would still qualify for deduction 
under section 165." The court, however, declined to comment on whether 
the converse was true: whether a payment that would be deductible under 
the narrow constraints of section 162(f) would always be deemed to pass 
the public policy test that might still apply to section 165. This 
leaves open the question of the applicability of pre-1969 public policy 
law to deductions not under section 162.
Foreshadowing the dissent in Allied-Signal, the Second 
Circuit also emphasized that Stephens' payment was made to Raytheon and 
not to a government. It disagreed with the tax court's conclusion that 
Stephens' distinction was irrelevant. "To the extent that ... a 
restitution payment, ordered in addition to punishment and paid directly 
to a victim, would not be a deductible loss, we respectfully disagree. 
In codifying the public policy exception to deductibility of expenses 
under section 162, Congress was clear and specific, limiting the 
exception to bribes, kickbacks and other illegal payments; a portion of 
treble damage payments; and fines and similar penalties paid to a 
government. That codification was intended to be 
'all-inclusive.'"16
Other Issues and Strategies
Payments to a Government. The IRS in recent years 
has generally accepted the significance of the requirement that punitive 
payments, to be nondeductible, must be made to a government. Thus, the 
IRS in FSA 1999-1054 indicated that an insurance company was not barred 
by section 162(f) from taking a deduction for punitive damages it paid 
to an insured employer to settle a civil lawsuit. The IRS, however, has 
taken an expansive view of what constitutes "a government."
In FSA 1999-1006, the Federal Reserve Bank (FRB) assessed a 
deficiency penalty on a member bank. The FSA found the penalty not 
deductible under section 162(f). The bank had deducted the penalty on 
the theory that it was a compensatory or remedial penalty. In 
disagreeing, the IRS relied on the facts that 1) the reserves were not 
interest-bearing and thus there was no loss necessitating compensation 
to the FRB; and 2) the FRB could waive the penalty, which is a feature 
of punitive fines. Was the payment to the FRB a payment to a government 
agency? Implicitly, the IRS answered "yes" - given that the FRB is an 
independent watchdog of federal government fiscal policy.
FSA 1997-26, in contrast, dealt with fines imposed on a member of a 
regulated trading exchange for violating exchange rules and faced 
squarely the question of the limitations of the requirement under 
section 162(f) that payments be made to a government. To "insure fair 
trading practices and honest dealing and provide a measure of control 
over speculative activity," explained the FSA, regulation is 
accomplished through a federally mandated duty of self-policing by 
exchanges.
The FSA then observed that "[a]ccordingly, for purposes of section 
162(f), we could argue that pursuant to this statutory scheme, exchanges 
in the performance of their mandatory self-regulatory duties are acting 
as delegatees of the CFTC [and SEC].... Under this congressional design, 
exchanges are imbued with quasi-governmental power that transforms them 
from private trade associations into organizations sharing 
responsibility for the maintenance of an orderly and fair 
market."17 "Accordingly, when an exchange 
conducts disciplinary proceedings under self-regulatory power conferred 
upon it, it may be considered, under certain circumstances, to be 
engaged in governmental action, federal in character.... [A] strong 
argument exists that when engaged in the enforcement of federally 
mandated rules and regulations the actions of these hybrid organizations 
are sufficiently governmental in nature to trigger application of 
section 162(f)."
In other words, the IRS position is that penalties imposed by what it 
deems self-regulating organizations are imposed by a government for 
section 162(f) purposes.
Settlements Ahead of Government (or other Claimant) 
Action. Codification of another part of the public policy 
doctrine is contained in section 162(g). This section addresses 
settlements made under the federal antitrust laws. Two-thirds of any 
amounts paid for damages are rendered nondeductible by this provision, 
which, like section 162(f), was enacted in 1969. The question in FSA 
2001-43006 was what happens when the taxpayer beats a claimant to the 
punch.
FSA 2001-43006 involved a taxpayer that pleaded guilty to Sherman Act 
violations. The taxpayer entered into a settlement with a claimant who 
had not yet filed a civil suit against it but who presumably could have 
sued for triple damages. If the suit had been filed, and then settled, 
the payments made would have been allowed only to the extent of 
one-third of the damages, explained the FSA. However, because no suit 
was ever filed, section 162(g) did not apply.
The government previously lost on that point in Fisher Cos. v. 
Commissioner.18 In Fisher, 
the tax court read the plain language of the statute as requiring that 
an action be brought under the triple damages provision to trigger the 
two-thirds disallowance rule. Without the filing of a complaint, 
therefore, the mere fact that the antitrust violation was the basis for 
settlement makes no tax difference. This clearly is a situation in which 
settlement before the claimant gets
to the courthouse can be good tax planning.
A similar case can be made in connection with IRS trust fund recovery 
penalties. Such penalties, equal to the unpaid trust fund portion of 
employment-related taxes, can be assessed against the responsible 
officers of an entity.19 The law is clear 
that after such an assessment, the responsible officer cannot deduct 
those payments because the payments are treated as a nondeductible 
penalty under section 162(f).20
Although no reported cases on the issue appear to exist, a potential 
responsible officer who is entitled to indemnification from the entity 
and who pays the tax on behalf of the entity before the IRS assesses the 
trust fund recovery penalty may be entitled to a business or nonbusiness 
bad debt deduction under section 165(c).21
Conclusion
The outcome of government claims usually involves negotiation of some 
sort of settlement, often without any court-level proceeding ever 
commencing. For section 162(f) purposes, the fact that something is paid 
under a settlement does not, standing alone, make it any more deductible 
than if it is paid under a court order. When sections 162(g) or 6672 are 
involved, however, deductibility may turn on whether a settlement or 
payment was made before any litigation or payment was commenced.
The likelihood of a tax deduction is increased if language in the 
settlement documents recites that the payments to be made are 
compensatory and not punitive and that the government representatives 
agree that a tax deduction should not be barred under section 162(f) or 
on public policy grounds. If the amount being paid in a settlement 
exceeds damages actually sustained, an explanation of the difference 
ought to be made; for example, that it is intended to reimburse the 
government for its investigative costs and for interest on the 
underlying amount. The possibility should always be explored of crafting 
a settlement so that compensatory payments are made - such as to victims 
of an alleged securities fraud - rather than punitive payments being 
made to government agencies.
The stakes are huge. Ask Merrill Lynch & Co., or Exxon, or 
Salomon Brothers. Merrill Lynch's recent $100 million dollar settlement 
with the New York attorney general's office is probably - by virtue of a 
well-crafted agreement - deductible. So was almost all of Exxon's $1 
billion Exxon Valdez oil spill settlement. So was $100 million of a 
Salomon Brothers settlement in the early 1990s with the SEC over 
manipulation of the U.S. Treasury bond market. A company confronting 
this issue is almost always better served with early planning.
Endnotes
1McKinnon, 
Firms Accused of Chicanery Could Get IRS Tax Break, Wall St. 
J., Sept. 3, 2002, at A4. See also Zuckerman, Wall Street's 
Settlement Will Be Less Taxing, Wall. St. J., Feb. 13, 2003, at C1 
("Wall Street firms are getting ready to pay out billions of dollars to 
resolve alleged stock research abuses. But the pain will be much easier 
to take, thanks to U.S. taxpayers. The reason: Most of the payments 
likely will be tax deductible for the companies.").
2This article was 
inspired by an excellent discussion of the subject by Burgess J.W. Raby 
and William L. Raby appearing in 34 Tax Practice 109 (May 3, 2002).
315 U.S.C. § 
1125(c).
468 T.C.M. (CCH) 
1412 (1994).
5116 F.3d 382 (9th 
Cir. 1997).
695-1 U.S.T.C. 
(CCH) ¶50,151 (3d Cir. 1995).
7Id. at 
p. 87,540.
8Id. at 
p. 87,541.
9Id. at 
p. 87,542.
10Id. 
at p. 87,543.
11Id.
12880 F.2d 1311 
(Fed. Cir. 1989).
13See 
42 U.S.C. § 7413 (authorizing civil penalties and injunctive relief 
for violations of the Clean Air Act) and 33 U.S.C. § 1319 
(authorizing civil penalties and injunctive relief for violations of the 
Clean Water Act). The standard form EPA consent decree contains explicit 
language that the payment is nondeductible. In environmental cases in 
which the EPA and a state environmental tax authority exercise 
concurrent jurisdiction, a private party may wish to investigate whether 
a better tax result might be gained by settling with the state 
enforcement authority under a state statute.
14Raby, 
supra note 2, at 114.
15905 F.2d 667 
(2d Cir. 1990).
16Id. 
at 674. Note that the tax court in Stephens held that losses 
under section 165(c)(2) were still subject to a broad public policy 
test. While the Second Circuit reversed, it made clear that it agreed 
with the tax court that the standard for a deduction under section 165 
is no less demanding than under section 162(f). That, of course, leaves 
open for future cases the possibility of the IRS disallowing deductions 
claimed under sections other than 162 on public policy grounds even 
broader than those set forth in section 162(f).
17Sacks v. 
Reynolds Securities Inc., 593 F.2d 1234, 1244 (D.C. Cir. 1978).
1884 T.C. 1319 
(1985), aff'd, 806 F.2d 263 (9th Cir. 1986).
1926 U.S.C. 
§ 6672 (1986).
20Elliott v. 
Commissioner, 73 T.C.M. (CCH) 3197 (1997).
21Presumably, 
the same theory would apply to the payment of Wisconsin trust fund taxes 
ahead of a responsible officer assessment under, for example, Wis. Stat. 
section 71.83(1)(b)2. or 77.60(9).
Wisconsin Lawyer