1 

 UNITED STATES DISTRICT COURT 

 NORTHERN DISTRICT OF INDIANA 

 SOUTH BEND DIVISION 

UNITED STATES OF AMERICA 

 VS. 

JAMES A. SIMON

) 

) 

) 

) 

)

CAUSE NO.:3:14-CV-2025-RLM

(ARISING FROM 3:10-CR-0056-RLM)

 

 OPINION AND ORDER 

In November 2010, a jury found James A. Simon guilty of filing false tax 

returns, failing to report his interest in foreign bank accounts, mail fraud, and 

federal financial aid fraud. The court sentenced Mr. Simon to a total of 72 months 

imprisonment to be followed by three years of supervised release, and the court 

of appeals affirmed the conviction and sentence. Mr. Simon now moves to vacate, 

set aside, or correct his sentence under 28 U.S.C. § 2255. For the reasons that 

follow, the court denies Mr. Simon’s motion. 

I. BACKGROUND

The factual background underlying Mr. Simon’s conviction is set out in 

detail in the court of appeals’ opinion denying Mr. Simon’s direct appeal. United 

States v. Simon, 727 F.3d 682 (7th Cir. 2013). Because Mr. Simon’s “business 

dealings require a flowchart to unravel,” id. at 683, the court recites only the 

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facts needed to resolve the specific arguments Mr. Simon raises in his § 2255 

motion. 

Mr. Simon was a certified accountant, professor of accounting, and 

entrepreneur with interests in several businesses and entities. One of those 

ventures was JAS Partners, a domestic limited partnership in which Mr. Simon 

and his wife each had a one percent partnership stake and the Cook Islandsbased Simon Family Trust owned the other 98 percent. Another of Mr. Simon’s 

ventures was Elekta Ltd., a corporation chiefly owned by Mr. Simon’s retired 

sisters but entrusted wholly to Mr. Simon’s management. Elekta owned nineteen 

percent of a third venture that Mr. Simon managed, JS Elekta. JS Elekta in turn 

owned 75 percent of a fourth business, Ichua Company, also managed by Mr. 

Simon. Of those four businesses over which Mr. Simon had signature authority, 

three – Elekta, JS Elekta, and Ichua – were foreign entities possessing foreign 

bank accounts. 

This case is about money that Mr. Simon paid to himself from those four 

entities and from another domestic venture, William R. Simon Farms. Between 

2003 and 2006, Mr. Simon (or his immediate family members) received about 

$1.8 million combined from the businesses, which Mr. Simon spent on personal 

and family expenses and recorded as loans in his personal financial records. No 

promissory notes existed for these purported loans, and Mr. Simon paid no 

interest to the companies that made them. He repaid a small portion of the 

principal to JAS Partners after becoming aware of the government’s investigation 

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into his finances. He reported none of this money as income on his tax returns. 

In 2005 Mr. Simon paid less than $400 in taxes, and in each of the other three 

years between 2003 and 2006 he paid no taxes at all and claimed a refund. None 

of the tax returns disclosed that Mr. Simon had interests in or control over 

foreign bank accounts. Mr. Simon prepared and filed these tax returns himself. 

During these years, Mr. Simon filled out need-based financial aid 

applications for the private schools his children attended. On these applications, 

he reported that he had no or very little income, suffered large debts or losses, 

spent no money on clubs or vacations, had only a few thousand dollars of assets, 

was in a precarious financial situation due to business failures and litigation, 

and had enough money to keep him “afloat but barely.” These representations 

were all false: Mr. Simon had the payments from his businesses, spent lavishly 

on several expensive club memberships, and could afford vacations to Europe 

and Disney World in addition to a comfortable lifestyle for himself and his family. 

Based solely on these applications and the tax forms Mr. Simon submitted, the 

schools gave the Simon family a total of $120,000 in need-based financial aid. 

Mr. Simon also filled out federal “FAFSA” financial aid applications for one of his 

daughters to attend college. As he did on his private financial aid applications, 

Mr. Simon reported minimal gross income and assets on the FAFSA application. 

In November 2007, IRS agents searched Mr. Simon’s house pursuant to a 

warrant. Mr. Simon hired attorneys soon after that and began preparing a 

defense to possible charges. His attorneys hired a team of investigators and 

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conducted their own investigation into Mr. Simon’s finances, including 

interviewing the people already interviewed by government agents. Mr. Simon’s 

defense team also met with prosecutors to discuss the probable charges, to guide 

their planning of colorable defenses. 

In April 2010, Mr. Simon was charged in a 23-count indictment. Counts 

1-4 alleged that Mr. Simon filed false tax returns for the years 2003-2006. The 

tax returns were allegedly false in that they underreported income, and in that 

they didn’t check the “yes” box of Line 7a on Schedule B to IRS Form 1040. The 

question associated with Line 7a asked whether Mr. Simon had any interest in 

or authority over foreign accounts. Counts 5-8 charged Mr. Simon with failing to 

file forms called Reports of Foreign Bank and Financial Account, or “FBARs,” for 

the years 2004-2007. FBARs concern foreign financial accounts, and a person 

is required to file them if he or she has an interest in or signature authority over 

foreign accounts worth more than $10,000. Counts 9-19 charged Mr. Simon with 

mail fraud related to the need-based financial aid applications he made to the 

private schools his children attended. Those counts alleged that Mr. Simon 

underreported his income on the forms, and that the tax returns he attached 

were fraudulent for the same reasons as alleged in counts 1-4. Counts 20-23 

charged Mr. Simon with federal financial aid fraud based on the FAFSA forms he 

filled out on his daughter’s behalf. The FAFSA application required Mr. Simon to 

include information from his tax returns; if the tax returns were false (as alleged 

in counts 1-4), the aid applications were fraudulent as well. 

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At trial, Mr. Simon’s defense to the tax fraud counts was generally that the 

$1.8 million he received from his business entities wasn’t taxable income. He 

primarily characterized the money as funds loaned to him legitimately by his 

businesses, and which he intended to pay back. He suggested in the alternative 

that the payments could be considered nontaxable partnership distributions 

rather than taxable income. With regard to not checking the “yes” box on the 

part of Schedule B of his tax returns asking whether he had interest in or control 

over any foreign bank accounts, Mr. Simon’s defense was that he used TurboTax 

software to automatically fill out his tax forms. Based on how he answered the 

program’s questions, the program didn’t ask him anything about foreign 

accounts. His defense as to the FBAR reporting requirements was that the 

requirements were confusing, and in any case filing or not filing them had no 

effect on tax liability so there would be no reason for him to intentionally conceal 

his control over the foreign accounts. With regard to the mail fraud and financial 

aid fraud counts, Mr. Simon’s defense was that if the jury accepted his 

explanations on the tax and FBAR issues – that the money wasn’t taxable income 

and he didn’t think he had to file the FBARS – then none of the statements on 

the financial aid applications were false. In addition, for the private financial aid 

applications, even if his statements about his income and assets were false they 

weren’t materially so; because his children were high-performing academically, 

the schools wanted them to attend and essentially made price concessions on 

tuition. He argued that the schools themselves had instructed him to just 

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estimate the information on the forms, because the answers wouldn’t really affect 

the amount of tuition his family would have to pay. 

After a six-day trial, the jury mostly rejected these explanations. The jury 

found Mr. Simon not guilty of three of the mail fraud counts but guilty as to the 

other twenty counts in the indictment. The court sentenced Mr. Simon to an 

aggregate term of 72 months imprisonment and an aggregate term of 3 years of 

supervised release.1 The court of appeals affirmed the conviction in all respects, 

and Mr. Simon timely filed this motion to vacate under § 2255. 

A federal prisoner can challenge his sentence on the ground that the 

sentence was “imposed in violation of the Constitution or laws of the United 

States, or that the court was without jurisdiction to impose such sentence, or 

that the sentence was in excess of the maximum authorized by law, or is 

otherwise subject to collateral attack.” 28 U.S.C. § 2255. Mr. Simon is entitled 

to relief under § 2255 only if he can show a “fundamental defect which inherently 

results in a complete miscarriage of justice,” United States v. Addonizio, 442 U.S. 

178, 185 (1979), or “an omission inconsistent with the rudimentary demands of 

fair procedure,” Hill v. United States, 368 U.S. 424, 428 (1962). 

Issues not argued and decided on direct appeal can’t ordinarily be raised 

in a § 2255 petition unless the petitioner can show good cause and actual 

 

1 Mr. Simon notified the court that he anticipated being released to home confinement on June 

1, 2016 and so may no longer be in custody. Nonetheless, he has notified the court that he 

intends to pursue relief under § 2255 despite his release, and he is entitled to do so because he 

was in custody when he filed his petition. See Virsnieks v. Smith, 521 F.3d 707, 717-718 (7th 

Cir. 2008).

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prejudice for the procedural default. Galbraith v. United States, 313 F.3d 1001, 

1006 (7th Cir. 2002). Claims of ineffective assistance of counsel are an exception, 

and can still be argued in a § 2255 petition even if not raised on direct appeal. 

See Massaro v. United States, 538 U.S. 500, 504 (2003) (holding that “an 

ineffective-assistance-of-counsel claim may be brought in a collateral proceeding 

under § 2255, whether or not the petitioner could have raised the claim on direct 

appeal.”). 

The court in which a § 2255 motion is brought must hold an evidentiary 

hearing if affidavits or other competent proof establishes a dispute as to a 

material factual issue. See Taylor v. United States, 287 F.3d 658, 660 (7th Cir. 

2002). An evidentiary hearing isn’t required if “the motion and files and records 

of the case conclusively show that the petitioner is entitled to no relief,” 28 U.S.C. 

§ 2255 (2012), or if the petitioner’s factual allegations are purely speculative. See 

Gallo-Vasquez v. United States, 402 F.3d 793, 797 (7th Cir. 2005) (“[A] hearing 

is not necessary if the petitioner makes conclusory or speculative allegations 

rather than specific factual allegations.”) (alteration in original) (internal 

quotation marks omitted). 

Based on Mr. Simon’s § 2255 motion and the record of this case, the court 

concludes that the factual and legal issues raised can be resolved on the record 

and no hearing is necessary. See Menzer v. United States, 200 F.3d 1000, 1006 

(7th Cir. 2000) (holding that a hearing is not required where the record 

conclusively demonstrates that a petitioner is entitled to no relief on his § 2255 

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motion). Even accepting all relevant facts as Mr. Simon alleges them, he hasn’t 

shown that he is entitled to relief. 

II. DISCUSSION

 Mr. Simon brings two general claims, both grounded in the allegation that 

his trial counsel provided constitutionally ineffective assistance. The Sixth 

Amendment guarantees criminal defendants the right to constitutionally 

sufficient representation by an attorney. This right provides for only “a 

professionally competent defense, not for the best possible defense.” Rutledge v. 

United States, 230 F.3d 1041, 1053 (7th Cir. 2000) (quoting Holman v. Gilmore, 

126 F.3d 876, 883 (7th Cir. 1997)). To prevail on an ineffective assistance of 

counsel claim, Mr. Simon must show both that his attorneys’ performance “fell 

below an objective standard of reasonableness” and that there is a reasonable 

probability that, but for his attorneys’ errors, the result of the proceeding would 

have been different. Strickland v. Washington, 466 U.S. 668, 688-693 (1984). 

This is a difficult standard to meet; to prevail, Mr. Simon must show both “that 

counsel made errors so serious that ‘counsel’ was not functioning as the counsel 

guaranteed the defendant by the Sixth Amendment” and “that counsel’s errors 

were so serious as to deprive [Mr. Simon] of a fair trial, a trial whose result is 

reliable.” Strickland v. Washington, 466 U.S. at 687; see also Kimmelman v. 

Morrison, 477 U.S. 365, 374 (1986) (“The essence of an ineffective-assistance 

claim is that counsel’s unprofessional errors so upset the adversarial balance 

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between defense and prosecution that the trial was rendered unfair and the 

verdict rendered suspect.”). 

With regard to the performance prong of the Strickland inquiry, there is a 

strong presumption that counsel performed effectively. See Berkey v. United 

States, 318 F.3d 768, 772 (7th Cir. 2003). “A court’s scrutiny of an attorney’s 

performance is ‘highly deferential’ to eliminate as much as possible the distorting 

effects of hindsight, and we ‘must indulge a strong presumption that counsel’s 

conduct falls within the wide range of reasonable professional assistance.’” 

Vinyard v. United States, 804 F.3d at 1225 (quoting Strickland v. Washington, 

466 U.S. at 687). The reasonableness of counsel’s performance must be 

evaluated “from counsel’s perspective at the time of the alleged error and in light 

of all the circumstances” known to counsel at the time. Kimmelman v. Morrison, 

477 U.S. at 381. An attorney’s performance is judged holistically, and even a 

clear mistake doesn’t amount to constitutionally ineffective assistance where the 

attorney’s performance was competent on the whole. See Dahler v. United States, 

143 F.3d 1084, 1086 (7th Cir. 1998) (noting that “it is essential to examine the 

attorney’s entire work product; an isolated slip-up in an otherwise competent 

representation does not violate the sixth amendment”). Because reviewing courts 

shouldn’t second-guess counsel’s strategic choices, the burden of showing that 

counsel’s decisions fell outside the wide range of reasonable strategic choices 

“rest[s] squarely on the defendant.” Burt v. Titlow, 134 S. Ct. 10, 12, 187 L. Ed. 

2d 348 (2013). “The question is whether an attorney’s representation amounted 

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to incompetence under prevailing professional norms, not whether it deviated 

from best practices or most common custom.” Makiel v. Butler, 782 F.3d 882, 

897 (7th Cir. 2015) (internal quotation marks omitted). 

“Even if counsel’s performance was deficient, a petitioner must also show 

that ‘there is a reasonable probability that, but for counsel’s unprofessional 

errors, the result of the proceeding would have been different,’ meaning ‘a 

probability sufficient to undermine confidence in the outcome.’” Eckstein v. 

Kingston, 460 F.3d 844, 848 (7th Cir. 2006) (quoting Strickland, 466 U.S. at 

694). While a petitioner must do more than just show that counsel’s errors had 

some conceivable effect on the outcome, he “need not show that counsel’s 

deficient conduct more likely than not altered the outcome in the case.” 

Strickland, 466 U.S. at 693. “In weighing the effect of counsel's errors, the court 

must consider the totality of the evidence. . . A verdict or conclusion that is 

overwhelmingly supported by the record is less likely to have been affected by 

errors than one that is only weakly supported by the record.” Eckstein v. 

Kingston, 460 F.3d at 848 (quoting Hough v. Anderson, 272 F.3d 878, 891 (7th 

Cir. 2001)). 

Both the performance and prejudice prongs of the Strickland inquiry must 

be satisfied before a prisoner is entitled to relief, and if a claim fails under either 

prong the claim fails and the court need not address the remaining prong. See

United States v. Taylor, 569 F.3d 742, 748 (7th Cir. 2009) (“Courts may deny 

ineffective assistance of counsel claims for lack of prejudice without ever 

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considering the question of counsel’s actual performance.”); Milone v. Camp, 22 

F.3d 693, 703 (7th Cir. 1994) (“The Court need not address both Strickland 

prongs if it is clear that [the petitioner] cannot satisfy one of them”). 

As an initial matter, both Mr. Simon and the government focus heavily on 

matters that aren’t actually material to resolving the claims in the § 2255 motion. 

The government points extensively to outward indicia of diligence on the part of 

Mr. Simon’s lawyers – the number of attorneys Mr. Simon had, the quantity of 

investigators and experts they hired, the sheer volume of pretrial, mid-trial and 

post-trial motions, and the extensive presentation of evidence at trial and 

sentencing. The government is correct that the constitutional effectiveness of 

trial counsel should be examined holistically. “Isolated errors do not constitute 

ineffective assistance if the attorney’s work product taken as a whole 

demonstrates competence.” Rutledge v. United States, 230 F.3d 1041, 1053 (7th 

Cir. 2000). 

But sheer activity doesn’t equate to constitutional effectiveness. A large, 

expensive defense team filing a flurry of motions might still be ineffective if their 

decision making on a critical point falls below an objective standard of 

reasonableness, just as a single attorney doing nothing other than negotiating a 

quick plea can be constitutionally effective. See Premo v. Moore, 562 U.S. 115, 

123-125 (2011). Pointing to all the dust Mr. Simon’s attorneys kicked up before 

and during trial doesn’t resolve the question of whether some specific acts or 

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omissions fell below a professional standard of reasonableness such that Mr. 

Simon was denied the effective assistance of counsel. 

At the same time, Mr. Simon makes voluminous factual allegations and 

arguments about the defense team’s pre-trial game plan and whether his 

attorneys followed it. Mr. Simon insists that his pretrial agreement with his 

attorneys as to what defense they would pursue is relevant because it shows his 

counsel knew the agreed-on defense to be the best available one. Even if Mr. 

Simon is correct that he and counsel agreed on a strategy before trial and that 

the strategy eventually pursued at trial deviated from that plan, that doesn’t 

show ineffectiveness. For one thing, whether his attorneys provided the “best” 

available defense isn’t the issue in a § 2255 motion, because “[t]he Constitution 

calls for a professionally competent defense, not for the best possible defense.” 

Rutledge v. United States, 230 F.3d 1041, 1053 (7th Cir. 2000). For another 

thing, which strategy appears optimal might shift over time. “Trial tactics are a 

matter of professional judgment” and a reviewing court “will not play ‘Monday 

morning quarterback’ when reviewing claims that an attorney rendered 

constitutionally deficient representation in making decisions on how to best 

handle a case.” United States v. Malone, 484 F.3d 916, 920 & n. 1 (7th Cir. 

2007). 

There are countless legitimate strategic reasons an attorney might plan 

out a particular theory of the case before trial yet abandon it once proceedings 

are underway. A competent criminal defense attorney must adjust as the 

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government’s case unfolds and as government witnesses tell their story and 

experience cross examination. The need to see and experience those 

developments usually prevents pretrial plans from being set in stone. See Blake 

v. United States, 723 F.3d 870, 879 (7th Cir. 2013) (“Counsel’s performance is 

to be evaluated in light of the discretion properly accorded an attorney to develop 

appropriate trial strategies according to the attorney’s independent judgment, 

given the facts of the case, at least some of which may not be reflected in the 

trial record.”). Concerns such as these occasionally lead experience criminal 

defense counsel to waive or defer opening statements. 

In short, whether Mr. Simon got the defense he expected isn’t at issue – 

the court asks only whether the defense he actually got passes constitutional 

muster. For this reason, the “factual disputes” that Mr. Simon believes entitle 

him to an evidentiary hearing don’t. His affidavit and his counsel’s affidavit 

present different stories about how and why various defense decisions were 

made, but resolving those disputes isn’t necessary. In ruling on a § 2255 motion, 

the court looks at constitutional effectiveness from an “objective standard of 

reasonableness” – the question is whether there could have been any sound 

strategic reason for a particular act or decision, not what an attorney was 

actually thinking when making the choice. See Cullen v. Pinholster, 563 U.S. 

170, 196 (2011) (emphasizing that Strickland mandates a strong presumption of 

reasonableness, so a court reviewing an ineffectiveness claim is “required not 

simply to give [the] attorneys the benefit of the doubt, but to affirmatively 

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entertain the range of possible reasons [counsel] may have had for proceeding 

as they did.”) (internal quotation marks and citations omitted) (emphasis added); 

see also Harrington v. Richter, 562 U.S. 86, 110 (2011) (holding that Strickland 

“calls for an inquiry into the objective reasonableness of counsel’s performance, 

not counsel’s subjective state of mind.”). 

Mr. Simon first alleges that his counsel mistakenly thought the defense 

could call experts to testify as to principles of tax law, and so neglected to prepare 

jury instructions on the relevant legal principles. The jury therefore never heard 

a critical part of Mr. Simon’s defense, specifically that any mischaracterization 

of the payments he received wasn’t willful because other alternative tax 

treatments for the payments would have had the same result. His second claim 

alleges several different alleged errors by trial counsel which cumulatively 

impeded Mr. Simon’s attempt to present his defenses to the jury. 

A. Ineffectiveness related to Mr. Simon’s proposed willfulness-based defense 

As Mr. Simon describes it, his “primary contention is that he received 

ineffective assistance because trial counsel failed to provide timely and adequate 

law to the court.” In essence, he argues that he wanted to make a good-faith 

defense to the charge that he underreported his income on his tax returns, but 

his counsel made a fatal legal error that prevented him from presenting the legal 

basis for his planned defense to the jury. 

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According to Mr. Simon, counsel had always planned on a two-pronged 

defense to the portions of the tax fraud charges in counts 1-4 based on 

underreported income. First, counsel would argue that there was nothing false 

about the tax returns because the payments not reported as income were in fact 

legitimate nontaxable loans from the businesses to Mr. Simon. The argument 

would be that Mr. Simon honestly considered these legitimate loans, and 

intended to repay them. Second, counsel would argue that even if Mr. Simon was 

wrong to consider the payments nontaxable loans, the mistake couldn’t have 

been willful because the payments would have been untaxable no matter how 

they were characterized. If the money didn’t properly qualify as loans, it would 

have been either partnership distributions or advances on reimbursements for 

expenses that Mr. Simon paid on behalf of the businesses – and neither of those 

would have changed the tax treatment, because partnership distributions and 

reimbursements are both non-taxable. In other words, if the jury rejected his 

argument that the loans were legitimate, Mr. Simon wanted it to infer that he 

must not have intentionally lied about the payments because there would have 

been no tax benefit to doing so; at worst his mischaracterization of the money as 

loans was an honest mistake, because he would have owed no taxes on the 

payments no matter how they were classified. Mr. Simon emphasizes that he 

never intended “to present alternative or contradictory” defenses that the money 

was either loans or partnership distributions or expense reimbursements. 

Rather, he believes his attorneys should have presented the following “common 

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sense” question to the jury: “why would [Mr. Simon] willfully mischaracterize the 

money as loans, which ultimately caused him to owe significant taxes, when he 

could have characterized the money as a partnership distributions [sic] or even 

income and owed none?” 

For jurors to understand and accept that defense, they’d need to know 

how the tax laws treat all those different categories of payments. The proper way 

to educate the jury about tax law principles is by submitting timely and legally 

correct jury instructions, not by calling expert witnesses; only the court can 

instruct the jury on the law, and expert witnesses can’t generally testify as to 

what the law is or whether someone’s conduct was or wasn’t lawful. See United 

States v. Jungles, 903 F.2d 468, 477 (7th Cir. 1990). Mr. Simon’s attorneys tried 

to call tax law professionals as expert witnesses, telling the court that the 

witnesses would opine on how the tax laws treat various types of payments and 

whether the payments at issue here were taxable. The court refused to permit 

such testimony, a holding that was upheld on appeal. See United States v. 

Simon, 727 F.3d 682, 697 (7th Cir. 2013) (“The court was correct to preclude 

any witness from generally explaining the law to the jury.”). 

After the witnesses’ testimony was excluded, the only available course for 

Mr. Simon’s attorneys was to propose jury instructions supporting his theory of 

defense. Because his counsel thought they could call experts instead, Mr. Simon 

says, they were caught off guard when the experts were excluded and didn’t have 

time to formulate adequate jury instructions. Counsel submitted jury 

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instructions on how partnership distributions and expense reimbursements are 

treated under the tax laws, but didn’t do so until the final day of trial. The court 

refused to give the instructions because they were untimely, and also because 

they were inadequate; they didn’t explain to the jury how to calculate Mr. Simon’s 

basis in JAS Partners, and without knowing Mr. Simon’s basis the jury couldn’t 

have determined whether distributions from the partnership were nontaxable. 

Accordingly, the jury was left without any instruction on how the tax laws applied 

to partnership distributions and reimbursements or expense advances, and Mr. 

Simon argues that this left him without a full defense. 

“An attorney’s ignorance of a point of law that is fundamental to his case 

combined with his failure to perform basic research on that point is a 

quintessential example of unreasonable performance under Strickland.” Hinton 

v. Alabama, 134 S. Ct. 1081, 1089 (2014). Mr. Simon believes that his attorneys 

made such a fundamental misstep, erroneously believing that experts could 

testify as to what the law is and thus squandering the chance to prevent a 

meritorious defense. He argues that the attorneys clearly didn’t make a strategic 

choice to jettison the good-faith defense based on alternative characterizations 

of the payments as partnership distributions or reimbursements, because they 

tried to present this defense and were only prevented from doing so by their own 

elementary legal mistakes. He insists that his attorneys couldn’t have 

strategically chosen to call experts to testify on the law because such experts 

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would obviously be excluded by the court, and they couldn’t have strategically 

chosen to submit untimely and inadequate jury instructions. 

That Mr. Simon’s counsel wound up on the wrong side of an evidentiary 

ruling doesn’t mean that they made a fundamental legal error that prevented Mr. 

Simon from mounting a full and reasonable defense. Counsel doesn’t act 

deficiently simply by pushing the envelope. There is an obvious strategic logic in 

at least trying to admit favorable but likely inadmissible evidence, or proposing 

favorable but likely improper jury instructions; if successful such efforts might 

secure the defendant an unreviewable acquittal, and if unsuccessful there’s no 

real cost to the defendant. Mr. Simon is certainly correct that there is never a 

valid strategic reason to submit untimely jury instructions as opposed to timely 

ones, but his argument that this mistake made his trial unfair presupposes that 

there was any legally valid way to present his chosen defense to the jury. In fact, 

there was not. The court wouldn’t have permitted Mr. Simon’s preferred goodfaith defense to be presented to the jury even if his attorneys had submitted 

timely and correct jury instructions, because the defense Mr. Simon wanted to 

raise would have been wholly speculative given the evidence at trial. Even if his 

attorneys made a mistake by submitting jury instructions too late, this error 

couldn’t possibly have prejudiced Mr. Simon because the instructions would 

have been rejected even if timely. 

“A defendant is entitled to an instruction on his theory of defense only if 

‘(1) the instruction provides a correct statement of the law; (2) the theory of 

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defense is supported by the evidence; (3) the theory of the defense is not part of 

the government’s charge; and (4) the failure to include the instruction would 

deprive the defendant of a fair trial.’” United States v. Campos, 541 F.3d 735, 

744 (7th Cir. 2008) (quoting United States v. Millet, 510 F.3d 668, 675 (7th Cir. 

2007)). Mr. Simon’s theory doesn’t meet the second criterion, because it was 

wholly speculative. To convict Mr. Simon on counts 1-4, the government was 

required to prove only that he filed a return that he did not believe was true and 

correct to “every material matter.” United States v. Pansier, 576 F.3d 726, 736 

(7th Cir. 2009). Accordingly, the focus is on Mr. Simon’s own knowledge and 

intent; if he characterized the money as loans and the jury found that he knew 

the loans weren’t legitimate, it is no defense that other hypothetical 

characterizations of the money unknown to Mr. Simon might have been available 

that could have resulted in no tax liability. Wholly hypothetical or speculative 

mental state defenses such as the one Mr. Simon now insists his attorneys 

should have mounted are often raised, but routinely excluded. See, e.g., United 

States v. Zayyad, 741 F.3d 452, 460 (4th Cir. 2014) (“If the defendant wants to 

present a theory or belief that might have justified his actions, then he must 

present evidence that he in fact relied on that theory or belief.”); United States v. 

Curtis, 782 F.2d 593, 599 (6th Cir. 1986) (“Willfulness is personal. It relates to 

the defendant's state of mind. It does not exist in the abstract. Unless there is a 

connection between the external facts and the defendant’s state of mind, the 

evidence of the external facts is not relevant.”). 

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In United States v. Kokenis, 662 F.3d 919 (7th Cir. 2011), the defendant 

controlled a number of corporations and business entities and was charged with 

filing false tax returns by not reporting various payments as income. Id. at 922-

926. The defendant wanted to call tax experts to testify about an obscure “pool 

of capital” accounting theory under which the payments at issue could have been 

excluded from taxable income, and wanted to argue that the pool of capital 

theory “would have provided a layer of credibility to [his] argument that he did 

not act willfully” in characterizing the money as nontaxable. Id. at 929-930. The 

district court refused to admit this testimony and declined to give a jury 

instruction on good faith. The court of appeals affirmed, noting that whether the 

“pool of capital” theory might have been available to the defendant was irrelevant 

to whether he willfully filed false returns, because the “mere existence of the 

theory without evidence of [the defendant’s] knowledge of and reliance on the 

theory is insufficient to support the assertion of good faith.” Id. at 928. Because 

there was “no evidence that he actually relied on the pooling capital theory,” the 

defendant’s proffered evidence “would be irrelevant, confusing, and perhaps even 

misleading.” Id. 

Mr. Simon’s situation is much the same. He wanted to argue that his 

failure to list the payments as income wasn’t willful because several possible 

characterizations of the payments would have resulted in no tax liability to him. 

But there was no evidence that Mr. Simon relied on these alternate possible 

bases for escaping tax liability, and no evidence that he ever considered the 

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21 

possibility of characterizing the payments as partnership distributions or 

expense reimbursements. A defendant “only needs to demonstrate a foundation 

in evidence, ‘however tenuous,’ to support his theory, but a ‘mere scintilla of 

evidence ... is not sufficient to warrant a defense instruction.’” United States v. 

Canady, 578 F.3d 665, 672–73 (7th Cir. 2009) (quoting United States v. 

Buchmeier, 255 F.3d 415, 427 (7th Cir. 2001)). Not only could Mr. Simon point 

to nothing suggesting that he relied on the alternative income characterizations 

when deciding not to report the payments as income, there was affirmative 

evidence to the contrary. Mr. Simon consistently recorded the payments as loans 

in his own records, noted them as loans on the tax returns of the businesses 

making the alleged loans, and characterized them as loans in UCC documents 

and bankruptcy filings. This evidence that Mr. Simon exclusively categorized the 

payments as loans negates any possible inference that he might have relied on 

a good faith belief that the payments were something else. Like the defendant in 

Kokenis, Mr. Simon “seems to be asserting that just because there may be 

evidence to show that someone could have had a good-faith belief that he wasn't 

violating the law, then he should be able to present such evidence to the jury. 

Not so. Without any connection to his state of mind, such evidence is irrelevant.” 

Kokenis, 662 F.3d at 930; see also United States v. Trudeau, 812 F.3d 578, 591 

(7th Cir. 2016) (“When a defendant offers nothing but speculation to link a piece 

of evidence to his state of mind, the evidence is properly excluded unless the 

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22 

defendant offers corroboration that the evidence in fact influenced his mental 

state.”) (emphasis in original). 

Moreover, there was no prejudice to Mr. Simon. The government points 

out that there was even less justification for treating the payments as 

partnership distributions or expense reimbursements than there was for treating 

them as loans; the loan-based defense truly was the only one with even a shadow 

of support in the record. It’s unlikely the jury would have credited Mr. Simon’s 

willfulness defense had it been presented to them, because the record didn’t 

actually support characterizing the payments as the alternate forms of 

nontaxable transfers Mr. Simon proposes. It isn’t necessary to review the 

problems with a partnership or reimbursement-based defense here, however, 

because even if Mr. Simon had presented his willfulness-based defense and the 

jury had credited it against all odds, he would still have been convicted on the 

tax fraud counts. Counts 1-4 of the indictment alleged that Simon’s tax returns 

were fraudulent in two ways – underreporting income, and failing to disclose his 

interests in foreign accounts – and the jury only needed to find one willful, 

material falsehood to convict him on these counts. The willfulness-based 

argument that Mr. Simon claims was critical to his defense was only relevant to 

one of the two falsehoods, and would have provided no defense to the allegation 

that Mr. Simon’s tax returns were false because they didn’t disclose his foreign 

accounts on Schedule B of the returns. 

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The jury could have convicted on counts 1-4 based solely on the 

nondisclosure of foreign accounts and would almost certainly have done so, 

given that it convicted Mr. Simon of failing to file the required FBAR reports 

disclosing the same foreign accounts. Indeed, by convicting the FBAR counts the 

jury necessarily found that Mr. Simon had foreign accounts he was required to 

disclose. The only way the jury could have acquitted on the tax fraud counts, 

then, would be if jurors believed Mr. Simon’s failure to disclose wasn’t willful. 

Counts 5-8 also had a willfulness requirement, so this would have been highly 

unlikely; the jury would have had to find that Mr. Simon’s failure to disclose his 

foreign accounts in the FBAR reports was willful but that his failure to disclose 

those accounts on his tax returns was an honest mistake. Both at trial and on 

appeal, Mr. Simon took the position that the Schedule B accusations and the 

FBAR accusations stood or fell together. See United States v. Simon, 727 F.3d 

at 698 (“Both Simon and the government treated [the Schedule B issues] as 

coterminous with the FBAR issue. That is, if Simon prevailed on the FBAR issue, 

he could prevail on the Schedule B issue. On the other hand, if he lost on the 

FBAR issue, he also lost on his Schedule B defense.”). Because Mr. Simon lost 

on the FBAR issue, he would have lost on the Schedule B issue and the jury 

would have convicted him of tax fraud regardless of whether it believed his tax 

returns also understated his income. 

Mr. Simon isn’t entitled to relief on his “primary” claim: that his counsel’s 

elementary legal mistakes prevented him from mounting his planned defense 

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24 

that any underreporting of his income wasn’t willful, because the payments 

would still have been nontaxable if considered partnership distributions or 

expense reimbursements. He wouldn’t have been entitled to present his 

alternative tax law theories or the good-faith defense based on them to the jury 

regardless of what counsel had done, because there was no evidence Mr. Simon 

had ever actually considered or relied upon those alternate characterizations of 

the payments in preparing his returns. The law simply doesn’t support the 

willfulness-based defense Mr. Simon now insists he planned to raise, so 

counsel’s inability to present that defense to the jury couldn’t have been 

constitutionally ineffective performance. Moreover, the jury rejected Mr. Simon’s 

defense to the other alleged falsity on his tax returns – the failure to report foreign 

accounts in Schedule B. He would therefore have been convicted on the tax fraud 

counts in any case, and could have suffered no prejudice from his attorneys’ 

inability to present his willfulness-based defense regarding the characterization 

of the payments. 

B. Ineffective assistance related to the mail fraud charges 

Mr. Simon also argues that his attorneys provided constitutionally 

ineffective assistance in defending him against the mail fraud charges in the 

indictment. Counts 9-192 alleged that Mr. Simon committed mail fraud in the 

 

2 The jury convicted Mr. Simon of most of the mail fraud counts, but acquitted him with regard 

to the three specific mailings involved in counts 13, 14, and 16. 

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course of sending financial aid applications to the private schools his children 

attended or sought to attend. The indictment alleged that Mr. Simon 

underreported his income on applications for need-based financial aid in the 

same way he underreported his income on his tax returns as alleged in counts 

1-4. Mr. Simon argues that his counsel failed to adequately investigate potential 

defenses to these charges. He says his counsel missed two legal infirmities in the 

indictment that could have formed the basis for meritorious motions to dismiss 

the mail fraud counts. He also claims that apart from these legal arguments, his 

attorney neglected to locate and call witnesses that would have been favorable 

to the defense. 

“Money or property” 

When a claim of ineffective assistance is based on counsel’s failure to 

present a motion, the court looks to whether the proposed motion would have 

been meritorious. See United States v. Cieslowski, 410 F.3d 353, 360 (7th Cir. 

2005); Owens v. United States, 387 F.3d 607, 610 (7th Cir. 2004). The inquiry 

turns to whether the legal arguments for dismissal that Mr. Simon now makes 

would have been successful if raised in a pretrial motion to dismiss or a midtrial motion for judgment of acquittal. 

The first legal infirmity that Mr. Simon identifies concerns whether his 

children’s private schools had a property right in the full value of tuition. To 

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26 

convict Mr. Simon of mail fraud, the government needed to prove that he used 

the mails in furtherance of “any scheme or artifice to defraud, or for obtaining 

money or property by means of false or fraudulent pretenses, representations, 

or promises.” 18 U.S.C.A. § 1341. The “money or property” targeted by the 

scheme need not be physical, tangible property, Carpenter v. United States, 484 

U.S. 19 (1987), but the victim must actually have a recognized property right in 

the object of the scheme at the time the fraud is committed. Cleveland v. United 

States, 531 U.S. 12, 15 (2000) (“It does not suffice, we clarify, that the object of 

the fraud may become property in the recipient's hands; for purposes of the mail 

fraud statute, the thing obtained must be property in the hands of the victim.). 

Mr. Simon insists that need-based financial aid doesn’t result in the 

transfer of any money or property from a school to a student’s family; the schools 

use need-based aid awards to reduce the amount of tuition they would otherwise 

charge, so they have no cognizable “property right” in the full price of tuition. 

The government responds that the private schools had a property right to the 

full amount of tuition, and that by fraudulently pleading poverty Mr. Simon 

induced the schools to offer his family a hefty tuition discount. 

Mr. Simon’s argument blinks the fact that he isn’t constitutionally entitled 

to a perfect defense; so long as his attorneys mounted a professionally reasonable 

defense, they were under no obligation to bring every conceivably colorable 

motion Mr. Simon can identify after the fact. As Mr. Simon himself 

acknowledges, “what may constitute money or property for the purpose of the 

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27 

[mail fraud statute] has been the subject of numerous appellate court decisions” 

and “circuit court opinions vary as to when a money or property right is 

implicated.” No controlling court opinion seems to have directly addressed 

whether underreporting income on financial aid forms satisfies the “money or 

property” element of the mail fraud statute, so to determine whether the charges 

against Mr. Simon should be dismissed his attorneys needed to navigate a 

tangled web of case law and compare his conduct to dozens of not-quiteanalogous schemes. Given the imprecise contours of the “property right” 

requirement and the difficulty of harmonizing the cases, even an attorney who 

incorrectly concluded that his client’s scheme fit the statute might not 

necessarily fall below the constitutional minimum of effective assistance. Put 

simply, on such complex and unsettled legal ground a professionally reasonable 

attorney is entitled to some room for error. That Mr. Simon can now in hindsight 

point to colorable legal arguments his attorneys didn’t raise doesn’t mean his 

constitutional right to counsel was violated. 

In any event, Mr. Simon’s counsel wasn’t ineffective because his proposed 

legal argument isn’t meritorious. He relies on Cleveland v. United States, 531 

U.S. 12 (2000), for the proposition that the mail fraud statute only applies when 

a victim is deprived of property actually in its hands at the time of the fraud. 

Cleveland concerned a scheme in which the defendants made false statements 

to the State of Louisiana to obtain video poker licenses. The defendants were 

convicted of defrauding the state, but the Supreme Court held that the 

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28 

convictions had to be reversed; because the defendants paid the required 

licensing fees and a share of their revenue to the state, the state hadn’t actually 

been deprived of any “money or property.” Id. at 22-23. The Court held that the 

state had only a regulatory interest in who received the licenses, not a cognizable 

property right for purposes of the mail fraud statute. 

Cleveland differs significantly from Mr. Simon’s case. Mr. Simon is right 

that under Cleveland, gain to the defendant isn’t enough to satisfy the mail fraud 

statutes without a corresponding loss to the victim of something in which the 

victim has a property right. But unlike in Cleveland, Mr. Simon’s false 

statements about his income deprived the private schools of something of value 

– the full price of tuition – that they would otherwise have received. The private 

schools didn’t have a mere “regulatory interest” in which students received needbased financial aid, because each award of aid meant an attending student paid 

less than full tuition; a spot in the class allocated to a student attending for free 

could otherwise have been occupied by a student paying full price. 

Mr. Simon’s reliance on United States v. Adler, 186 F.3d 574 (4th Cir. 

1999) is misplaced. Adler concerned a situation in which the defendant 

controlled a business that owed a debt to the victim, and that business received 

a large settlement payment from an unrelated suit. The defendant told the victim 

that he could pay the debt once the settlement proceeds came in. Realizing that 

he would have no money left if he used the settlement money to pay the debt, 

the defendant instead paid the settlement money to himself as a bonus. When 

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the company’s creditor demanded to know where the settlement money was, the 

defendant provided a fraudulent list of transactions that left out the payment to 

himself. The Fourth Circuit held that while the creditor had a legitimate right to 

payment of the debt, it had no property right in the particular money the 

defendant received from the unrelated settlement because the defendant never 

promised to pay the debt with those specific proceeds. Id. at 579-580. Mr. Simon 

misreads Adler as holding that a defendant’s promise to pay a debt isn’t enough 

to create a property right in the creditor to whom the promise is made. The Adler 

court didn’t reach that question at all because it explicitly found that no such 

promise existed. Id. at 578 (“Mr. Adler did undoubtedly tell Printgear that Adler 

Industries would be able to pay Printgear after it received the settlement ... But 

such a claim by Mr. Adler is a far cry from a promise to Printgear of that 

particular money, and the record reveals that no such promise was ever made.”). 

In any event, the relevance of Adler isn’t clear; there is no dispute here about 

whether the schools were entitled to any particular source of funds, only whether 

they were entitled to full tuition from someone who falsely claimed eligibility for 

a discount. 

Mr. Simon insists that nothing entitled the school to the full amount of 

tuition payment. Because the school offered price discounts to some families, he 

argues, the school couldn’t have had a property interest in the full amount of 

tuition; it only acquired an entitlement to the amount of tuition actually agreed 

upon after the need-based aid was awarded. The available authority belies that 

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argument: the relevant cases hold that a defendant who uses fraud to avoid 

paying the full amount due for a good or service deprives the victim of property 

within the meaning of the mail fraud statute. 

In Pasquantino v. United States, 544 U.S. 349 (2005), the Supreme Court 

held that defendants committed fraud3 when they devised a scheme to smuggle 

liquor out of Canada without paying excise taxes. The Court noted that “[t]he 

right to be paid money has long been thought to be a species of property,” so 

avoiding paying the taxes was no different than stealing money directly from the 

Canadian treasury. Id. at 355-356 (internal citations and quotation marks 

omitted). The private schools Mr. Simon’s children attended had a right to be 

paid money – children attending the schools were obligated to pay tuition. Mr. 

Simon made fraudulent statements to the schools to avoid paying the full 

amount due, and in so doing he deprived the schools of property in the form of 

their right to payment for the educational services they provided. 

Persuasive authority from other circuits concerning even more closely 

analogous circumstances uniformly holds that a defendant who lies about his 

eligibility for a discount deprives his victim of a property right in the full price of 

the good or service bought. In United State v. Ali, 620 F.3d 1062 (9th Cir. 2010), 

 

3 Technically wire fraud, but the wire and mail fraud statutes use identical language (aside 

from the jurisdictional element) and decisions based on one are commonly consulted in 

interpreting the other. See United States v. Turner, 551 F.3d 657, 666 n.4 (7th Cir. 2008) 

(“Cases construing the mail-fraud statute are equally applicable to cases involving violations of 

the wire-fraud statute.”). 

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the Ninth Circuit held that buyers deprived a software seller of property when 

they lied about their eligibility for a discount. The court held that the seller “had 

a right to full payment for its software and was deprived of that right when 

Defendants fraudulently obtained the software for less than full payment.” Id. at 

1067. Similarly, in United States v. Stewart, 872 F.2d 957 (10th Cir. 1989), the 

defendants lied about how they intended to distribute drugs to get a discount 

from the drug wholesaler. The court held that obtaining the fraudulent discount 

deprived the seller of property, because “the effect of the scheme was to deprive 

the manufacturers of money which they should have received” on the sale. Id. at 

960. Just like the victims in Ali and Stewart, the private schools in this case 

established particular criteria a customer had to fulfill in order to obtain a price 

discount. And just like the defendants in those cases, Mr. Simon misrepresented 

that he met those criteria in order to obtain a price concession to which he wasn’t 

legitimately entitled. 

Mr. Simon tries to distinguish Ali by pointing out that in that case, the 

defendant and the victim had a contract before the fraud that entitled the victim 

to payment. He emphasizes that he had no similar contract with the private 

schools, and that the entitlement to money that forms the basis of a protected 

property right must come from a contract or statute. But the reasoning in Ali 

made no mention of the prior contract, relying instead on common law 

entitlements of a seller to payment. Mr. Simon’s argument that a contract or 

statute is necessary to create a property right seeks to import into the case law 

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32 

limitations that don’t appear in it. He also tries to distinguish Stewart based on 

its age, suggesting that its reasoning depended partly on the gain to the 

defendant and that Cleveland later held that such gain to a defendant alone can’t 

support a mail fraud conviction. Mr. Simon misreads Stewart. Its reasoning 

doesn’t hinge on gain to a defendant alone, but rather on the fact that falsely 

representing one’s eligibility for a discount is intended to “gain money or property 

at the expense of the victim.” United States v. Stewart, 872 F.3d at 960. It is 

precisely this deprivation of the victim’s property that the mail fraud statute 

punishes. Stewart remains good law, its reasoning is persuasive, and its factual 

circumstances are so close to Mr. Simon’s that it is fatal to his argument that 

his particular misstatements were outside the scope of the mail fraud statute. 

For these reasons, Mr. Simon’s misrepresentation of his financial status 

to his children’s private schools deprived the schools of “money or property” 

under the mail fraud statutes and a motion to dismiss the mail fraud counts on 

that basis would have failed. Mr. Simon’s attorneys weren’t constitutionally 

ineffective in deciding not to bring a meritless motion to dismiss. 

Timing of the mailings 

The other argument Mr. Simon thinks should have been raised in a pretrial 

motion directed at some of the mail fraud charges concerns the timing of the 

mailings at issue. Counts 9-12 of the indictment concerned one particular 

private school, Canterbury School in Fort Wayne, Indiana. Three of Mr. Simon’s 

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33 

children attended Canterbury for the 2004-2005 school year, and Mr. Simon 

applied for need-based financial aid on behalf of all three. Mr. Simon’s financial 

aid applications were demonstrably false in a number of respects, including 

reporting that he spent no money on clubs or vacations the prior year when he 

was actually a dues-paying member of numerous expensive country clubs and 

had taken a vacation to Disney World. The mailings charged in counts 9-12 

weren’t the fraudulent financial aid applications, but rather the year-end billing 

statements confirming financial aid awards for each child that Canterbury 

mailed to Mr. Simon after the school year ended. Mr. Simon argues that if his 

attorneys had investigated further, they would have discovered that the 

statements were mailed at the end of the 2004-2005 school year and so came 

after the alleged fraud was complete and played no role in furthering it. 

Mr. Simon isn’t really complaining about evidence that could have been 

located but wasn’t; he simply wishes his attorneys had mounted a particular 

defense that they chose not to. The only thing Mr. Simon says would have been 

revealed by more “investigation” was the date of the mailings relative to the 

posting of financial aid awards. No investigation is needed to know that schools 

award financial aid at the beginning of the school year, and it seems unlikely 

that Mr. Simon’s large team of lawyers and investigators all remained wholly 

ignorant of the fact that the end-of-year billing statements charged in the 

indictment were mailed at the end of the year. Mr. Simon’s real claim seems to 

be that his lawyers were constitutionally ineffective in not moving to dismiss the 

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34 

Canterbury charges based on the timing of the mailings. 

Again, nothing in the constitution required Mr. Simon’s counsel to make 

every conceivably colorable argument. Counsel reasonably chose to defend the 

mail fraud charges on materiality grounds, arguing that because the schools 

wanted Mr. Simon’s academically gifted children to enroll, they were willing to 

make price concessions and told Mr. Simon that the financial information he put 

down in the applications wouldn’t really matter. This wasn’t an indefensible 

choice; that school officials didn’t consider themselves defrauded and in fact 

continue to support the Simon family could certainly have convinced a jury that 

the government was overreaching with these particular charges. In contrast, 

moving to dismiss because of the timing of the mailings would risk wasting 

valuable trial preparation time briefing a complex legal issue – time that could 

otherwise have been spent working on issues that didn’t concern only a tiny 

fraction of the government’s case against Mr. Simon. 

Regardless, Mr. Simon’s claim – whether viewed as an attack on his 

lawyers’ strategic choices or as a criticism of the scope of their investigation – 

falls apart for the independent reason that a motion to dismiss the charges based 

on the timing of the mailings wouldn’t have succeeded. The mail fraud statute 

doesn’t punish a scheme to defraud per se, but rather punishes use of the mails 

“for the purpose of executing such scheme or artifice or attempting so to do.” 18 

U.S.C.A. § 1341. Even an innocent, routine mailing by a third party containing 

no false statements itself can satisfy the statutory mailing element, provided that 

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35 

the mailing was part of the scheme as contemplated by the schemer. See

Carpenter v. United States, 484 U.S. 19, 28 (1987); Parr v. United States, 363 

U.S. 370, 390 (1960). The mailing at issue need not itself be an essential element 

of the scheme, but must be at least “incident to an essential part of the scheme,” 

Pereira v. United States, 347 U.S. 1, 8 (1954), or “a step in [the] plot,” Badders 

v. United States, 240 U.S. 391, 394, (1916). Even a mailing that occurs after the 

money or property targeted by the scheme has been received can fall within the 

scope of the statute, if it helps to conceal the fraud from detection or facilitates 

an ongoing scheme. See Schmuck v. United States, 489 U.S. 705, 711-712 

(1989). 

Mr. Simon emphasizes that the billing statements came in June 2005, 

after the 2004-2005 school year had ended and financial aid had already been 

awarded. He insists that the statements did nothing to conceal the scheme or 

make a later step in the scheme possible; they simply confirmed that no money 

was due on the accounts of Mr. Simon’s children. While Mr. Simon is correct 

that financial aid had already been fully paid out for the 2004-2005 year by the 

time these mailings occurred, he takes too narrow a view of the fraudulent 

scheme. As the government notes, Mr. Simon’s children continued to attend 

Canterbury for years after the 2004-2005 academic year.4

 Getting confirmation 

 

4 Mr. Simon initially argued that his children never returned to Canterbury after 2004-2005, so 

there was no ongoing scheme for the mailings to further after he received the 2004-2005 

financial aid. He abandons this argument in his reply brief, admitting that his children 

continued to attend Canterbury. 

USDC IN/ND case 3:14-cv-02025-RLM document 1 filed 07/05/16 page 35 of 51
36 

from the school that he owed no money at the end of the academic year proved 

to Mr. Simon that he had gotten away with it; a full year after the financial aid 

applications, Canterbury remained unsuspecting of his true financial status. 

“The relevant question at all times is whether the mailing is part of the execution 

of the scheme as conceived by the perpetrator at the time,” even if the mailing 

later proves to be documentation of the fraud that comes back to bite the 

schemer. Schmuck v. United States, 489 U.S. 705, 715 (1989). The billing 

statements reassured Mr. Simon that he remained in the school’s good graces, 

and because he hoped to continue sending his kids there (and would fill out 

further financial aid applications to do so), a rational jury could have found that 

the mailings were part of the scheme as conceived by Mr. Simon. Mr. Simon’s 

attorneys were accordingly not ineffective in declining to bring a motion to 

dismiss based on the timing of the mailings in counts 9-12. 

Mr. Turnbull’s testimony 

Mr. Simon’s final claim about his mail fraud counts is that had his 

attorneys more thoroughly investigated the charges against him, they would 

have identified and called Michael Turnbull as a witness. Mr. Turnbull was the 

director of admissions at Culver Academies, another private school Mr. Simon’s 

children attended, and oversaw the school’s financial aid committee during the 

years in question. Mr. Simon presents an affidavit from Mr. Turnbull, in which 

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37 

Mr. Turnbull says he doesn’t recall Mr. Simon’s investigators or attorneys 

contacting him and was never asked to testify as a witness at trial. Mr. Turnbull 

also states that Culver exercises discretion in awarding financial aid and uses it 

as a tool to offer price concessions, that when asked by parents about how to fill 

out spending information on the applications Mr. Turnbull would tell them to 

give their best guess, and that he sometimes encouraged parents to write “0” on 

the part of the forms asking how much the family could pay or to leave that 

question blank. Mr. Simon argues that had his attorneys interviewed Mr. 

Turnbull, Mr. Turnbull would have corroborated certain elements of Mr. Simon’s 

general defense that (1) his answers on the financial aid application weren’t 

materially false because the school doesn’t care much about those answers, and 

(2) he filled out the forms exactly as the school directed him to. 

An attorney representing a criminal defendant has a duty to make “some 

investigation into the prosecution’s case and into various defense strategies” or 

to “make a reasonable decision that makes particular investigations 

unnecessary.” Brown v. Sternes, 304 F.3d 677, 691 (7th Cir. 2002) (quoting 

Kimmelman v. Morrison, 477 U.S. 365, 384 (1986)). Accordingly, whether an 

attorney’s decision not to investigate a particular witness constitutes ineffective 

assistance depends on factors such as “counsel’s overall diligence, the likely 

relevance of the witness’s testimony, whether alternative ways of proving the 

point exist, and the strength of the government’s case.” United States v. Best, 

426 F.3d 937, 945 (7th Cir. 2005). As Mr. Simon’s own affidavit shows, his 

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38 

counsel conducted an extensive investigation that included interviewing the 

many people who had been interviewed by government agents. Critically, his 

attorneys interviewed Scott Joyner, Culver’s director of financial aid, four times 

before trial. Because Mr. Joyner sat on Culver’s financial aid committee and was 

familiar with Mr. Simon’s specific case, Mr. Simon’s attorneys could very 

reasonably have determined that a fishing expedition for other Culver employees 

who might have relevant testimony wasn’t an efficient use of their time. Even if 

Mr. Simon’s attorneys had missed a more favorable Culver witness, that doesn’t 

mean that the decision not to interview other Culver employees was 

unreasonable. 

Moreover, even if the limited investigation of Culver employees constituted 

deficient performance, Mr. Simon hasn’t met his burden of proving prejudice. A 

defendant raising an ineffective assistance of counsel claim regarding the failure 

to call a witness is only entitled to relief on such a claim if he makes a specific, 

affirmative showing as to what the missing evidence would have been, United 

States ex rel. McCall v. O'Grady, 908 F.2d 170, 173 (7th Cir. 1990), and proves 

that the witness’s testimony would have produced a different result, United 

States ex rel. Cross v. DeRobertis, 811 F.2d 1008, 1014 (7th Cir. 1987). Mr. 

Turnbull’s testimony, as reflected in his affidavit, falls far short of that showing. 

Mr. Turnbull says he can’t recall anything about what he did or didn’t discuss 

with Mr. Simon, and offers only general testimony about what he sometimes told 

other parents. He doesn’t say that he gave Mr. Simon specifically any 

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39 

instructions at all on how to fill out the aid applications. Mr. Simon complains 

that if interviewed at the time of trial Mr. Turnbull’s memory might have been 

clearer, but it is Mr. Simon’s burden of showing that testimony favorable to him 

wasn’t presented. A petitioner who claims his attorney’s failure to investigate 

violated his Sixth Amendment rights must “provide the court sufficiently precise 

information, that is, a comprehensive showing as to what the investigation would 

have produced.” Richardson v. United States, 379 F.3d 485, 488 (7th Cir. 2003). 

Mr. Simon’s speculation that an uncalled witness might have been able to 

corroborate his story isn’t enough to meet the exacting standards for habeas 

relief. 

In addition, even if Mr. Turnbull testified at trial and recalled giving Mr. 

Simon instructions on how to fill out the aid forms, that testimony wouldn’t have 

materially changed the outcome on the mail fraud counts. Even if Mr. Turnbull 

had told Mr. Simon to give a “best guess” as to his spending and encouraged him 

to write “0” for the amount of tuition he could pay, that wouldn’t excuse Mr. 

Simon from making specific false statements about his financial situation (such 

as complaining of phantom “major business failures”). The jury heard a wealth 

of evidence from which it could conclude that Mr. Simon’s financial aid form 

responses were not his “best guess” as to the previous year’s spending, given the 

wholesale disconnect between his actual lifestyle and his answers on the 

application. To the extent that Mr. Simon wanted to call Mr. Turnbull to testify 

that Culver wanted his children to attend and was willing to make concessions 

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to ensure that, the jury already heard such evidence from other witnesses. 

Mr. Simon can’t show either that his counsel’s decision not to interview 

Mr. Turnbull was unreasonable nor that it prejudiced his defense. 

C. Ineffective assistance related to the Schedule B filing requirements 

Next, Mr. Simon claims that his attorneys were ineffective in failing to 

investigate the filing requirements related to reporting foreign accounts on a tax 

return. Counts 1-4 of the indictment alleged that Mr. Simon filed false tax 

returns for the years 2003-2006. One of the ways the government argued Mr. 

Simon’s returns were false was that Mr. Simon hadn’t checked the “yes” box on 

Line 7a of IRS form 1040 Schedule B, which asks whether the filer has control 

over foreign financial accounts. Mr. Simon argues that his counsel was unaware 

that Line 7a doesn’t simply ask if the filer has control over any foreign account; 

rather, it asks whether the filer has control over one or more accounts with a 

combined value exceeding $10,000. Had his attorneys adequately investigated 

this requirement, Mr. Simon argues, they would have requested jury instructions 

concerning the $10,000 limit. The jury instructions actually given at trial didn’t 

inform the jury that they had to find Mr. Simon’s accounts totaled over $10,000 

to find that his not checking “yes” on the Schedule B forms was a falsehood. 

Alternately, Mr. Simon argues that if his attorneys were aware of the filing 

requirement they could have moved to dismiss based on a lack of proof that the 

accounts held over $10,000. 

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Given that Mr. Simon’s responses on the Schedule B forms wouldn’t have 

been false if his accounts totaled under $10,000, it was professionally 

unreasonable not to ensure that the jury was instructed on that point. But Mr. 

Simon isn’t entitled to relief because he can’t show prejudice from counsel’s 

error. For three of the four years at issue, the government proved at trial that 

Mr. Simon’s accounts did exceed $10,000 – no rational jury could have found 

otherwise, and a motion to dismiss those counts would have been dead in the 

water. Notably, the jury instructions for counts 5-8 (concerning Mr. Simon’s 

failure to file FBAR reports for the foreign accounts) did include the $10,000 

requirement, so in convicting Mr. Simon on those counts the jury necessarily 

found that his accounts met the minimum balance. And while the jury 

instructions didn’t mention the $10,000 limit specifically, the jury was still well 

aware of that limit; the government offered as an exhibit the IRS instructions for 

Schedule B, which clearly state that a taxpayer can check “no” on Line 7a if the 

combined value of the foreign accounts is under $10,000. The government’s 

closing argument explicitly directed the jury to consult these instructions during 

deliberations. 

For 2004, the situation is different. The government concedes that there 

was no evidence that Mr. Simon’s accounts met the minimum balance in that 

year – in fact, the government agreed to dismiss the 2004 FBAR count on that 

basis. Once the government made that admission, there was no excuse for Mr. 

Simon’s attorneys not moving to dismiss count 2 (the 2004 Schedule B count) 

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on the same basis; as both sides maintained throughout trial, the Schedule B 

and FBAR issues for each year stood or fell together. Still, the court agrees with 

the government that this error was a minor one in the context of the entire trial. 

No attorney is perfect, and the Sixth Amendment doesn’t entitle Mr. Simon to a 

flawless defense. His attorneys vigorously put the government to its burden of 

proof on every charge, and mounted colorable defenses on every issue. That they 

missed a clear winning argument on an issue relating to one part of a single 

count in a complex 23-count trial doesn’t mean they fell so far below professional 

standards of reasonableness that they weren’t functioning as counsel within the 

meaning of the Sixth Amendment. 

More importantly, Mr. Simon ignores that count 2 alleged two falsehoods 

on the tax return: checking “no” on Schedule B and underreporting income. Even 

had his attorneys noticed the $10,000 issue as to the 2004 Schedule B and 

successfully moved to dismiss, it wouldn’t have resulted in dismissal of count 2 

entirely because the allegations about income underreporting would survive. Mr. 

Simon could still be convicted on count 2 if the jury found that he underreported 

his income on his 2004 tax return. Mr. Simon’s defense to the income 

underreporting for 2004 was exactly the same as his defense to the alleged 

underreporting in every other year: he argued that the money he received 

constituted loans and didn’t need to be reported. The government’s evidence was 

strong that the money Mr. Simon considered loans actually wasn’t. And the jury 

convicted Mr. Simon on every other count that depended on his misrepresenting 

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his financial status, so it would be somewhat bizarre for the jurors to decide the 

payments from the 2004 returns were legitimate untaxable loans but all the 

other purported loans in the case were fraudulent. 

There simply isn’t a reasonable probability that the jury would have 

acquitted Mr. Simon on count 2 even if his attorneys had succeeded in getting 

the Schedule B allegations to that count dismissed, because the jury would have 

found that Mr. Simon’s 2004 tax return was false in underreporting his taxable 

income. Even if his attorneys provided ineffective assistance by not investigating 

the filing requirements of Schedule B, Mr. Simon hasn’t carried his burden of 

showing that such a deficiency prejudiced him. 

D. Ineffective assistance related to the TurboTax program 

Mr. Simon next claims that his attorneys conducted an inadequate 

investigation of the workings of the TurboTax software that Mr. Simon used to 

prepare his tax returns. As already discussed, counts 1-4 alleged that Mr. Simon 

didn’t disclose his control of foreign financial accounts totaling over $10,000 on 

Line 7a of Schedule B to the tax forms. Mr. Simon had such accounts, and for 

three of the four years charged his accounts met the $10,000 threshold requiring 

disclosure. Accordingly, his only available defense concerned his mental state: 

he didn’t realize he needed to disclose the accounts, and failed to check “yes” on 

Line 7a purely by mistake. 

According to Mr. Simon, he used a computer program called TurboTax to 

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prepare his tax returns for the years in question. He says he told his attorneys 

before trial that he didn’t think TurboTax asked him about foreign accounts and 

so didn’t prepare a Schedule B form for him. His attorneys subpoenaed a 

TurboTax representative to talk about what the version of the program Mr. Simon 

used would and wouldn’t have asked a user when automatically filling in Form 

1040, but apparently TurboTax never responded and no representative testified 

at trial. Mr. Simon insists that had his attorneys diligently followed up, a 

TurboTax representative could have testified in support of Mr. Simon’s defense 

that the program didn’t automatically prepare a Schedule B form because he 

never reported over $1,500 in interest income. Alternatively, his attorneys could 

simply have asked an expert witness to recreate Mr. Simon’s 2003-2006 tax 

returns using the versions of TurboTax from those years. He believes his 

attorneys provided ineffective assistance when they didn’t diligently pursue and 

develop his TurboTax-based defense. 

The decision by Mr. Simon’s counsel not to go into greater depth on the 

TurboTax program was very reasonable. The evidence Mr. Simon says should 

have been presented actually might have been fatal to his willfulness defense. 

The expert affidavit he attaches to his § 2255 motion makes absolutely clear that 

had he answered the programs’ questions truthfully, it would have prepared a 

Schedule B form and asked him about foreign accounts. This is so because there 

are two independent things that prompted TurboTax to print a Schedule B form: 

a user reporting over $1,500 in interest income or the user answering “yes” to 

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questions about whether the user “[had] an interest in a foreign account” (in the 

2003-2005 version of TurboTax) or “owned or signed on a foreign bank or broker 

or other financial account” (in the 2006 version). The evidence at trial clearly 

established that Mr. Simon had interests or signature authority over such foreign 

accounts; even now he doesn’t claim that he could have truthfully answered “no” 

to those questions. Had he answered those questions truthfully, TurboTax would 

have prepared a Schedule B form asking about the accounts regardless of the 

amount of interest income Mr. Simon reported. 5 His attorneys reasonably 

decided not to press the issue and stopped investigating the workings of 

TurboTax. When an attorney begins investigating an issue and correctly 

surmises that it won’t come out in his client’s favor, that attorney’s decision to 

cease the investigation is itself a strategic choice entitled to deference. 

Even if Mr. Simon’s lawyers could be said to have been professionally 

unreasonable in not following up on the subpoena to the TurboTax 

representative or having an expert recreate the returns, the error didn’t prejudice 

Mr. Simon. First and foremost, the jury heard this defense. Evidence was 

presented that Mr. Simon used TurboTax, and one of Mr. Simon’s expert 

witnesses testified that if an individual doesn’t report $1,500 of interest income 

in a particular year, “TurboTax doesn’t even print out the Schedule B.” The jury 

 

5 Mr. Simon’s only response on this point is that “any questions regarding an interest in a 

foreign account, distribution from a foreign trust, or owning or signing on a foreign account are 

asked at a different time in a catchall list of questions that are unrelated to interest income.” 

That is of course irrelevant; whenever the program asked the questions, Mr. Simon had an 

obligation to answer them truthfully.

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had Mr. Simon’s tax returns for the years in question, and could readily see that 

he didn’t report over $1,500 in interest income for any of the years between 2003 

and 2006. While Mr. Simon’s attorneys didn’t emphasize the defense by asking 

an expert to actually recreate Mr. Simon’s tax returns with the program, they 

nonetheless presented every necessary piece of the defense to the jury; the 

government even made clear in its closing argument that Mr. Simon’s defense to 

the Schedule B issue was that TurboTax didn’t print out Schedule B’s for him. 

Mr. Simon complains that his attorneys didn’t emphasize this defense enough, 

but doesn’t identify any specific part of the defense that wasn’t actually 

presented. 

The aborted investigation into a possible TurboTax-based defense didn’t 

constitute ineffective assistance of counsel, and even if it did there was no 

conceivable prejudice to Mr. Simon. Mr. Simon insists he is entitled to an 

evidentiary hearing on this issue, but doesn’t identify any factual disputes 

whatsoever on this point so no hearing is necessary. 

E. Ineffective assistance related to Mr. Simon’s testimony 

Lastly, Mr. Simon complains about the decision that he wouldn’t testify at 

trial. Mr. Simon suggests several pieces of evidence that he claims could only 

have come in through his own testimony, and several pieces of evidence admitted 

at trial that he claims could only have been rebutted by his testimony. Through 

an affidavit attached to his motion, Mr. Simon relates in detail his recollection of 

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how he and his attorneys discussed the prospect of Mr. Simon testifying. He 

identifies two errors that he believes constituted ineffective assistance: (1) his 

attorneys didn’t adequately prepare him and didn’t call him as a witness, and (2) 

they never explicitly informed him that the decision whether to testify was his 

alone. 

Anthony LaSpada, Mr. Simon’s lead defense counsel, submitted his own 

affidavit disputing essentially all the allegations in Mr. Simon’s affidavit about 

how the defense team approached the possibility of Mr. Simon testifying. One 

expert and one investigator who were both part of Mr. Simon’s defense team also 

submitted affidavits that generally corroborate Mr. LaSpada’s story and refute 

Mr. Simon’s. Mr. Simon believes these factual disputes necessitate an 

evidentiary hearing. 

Mr. Simon isn’t entitled to a hearing, for two reasons. The first is that a 

habeas petitioner can’t ensure himself an evidentiary hearing simply by 

providing an affidavit saying that his lawyer stopped him from testifying. “[T]his 

barebones assertion by a defendant, albeit made under oath, is insufficient to 

require a hearing or other action on his claim that his right to testify in his own 

defense was denied him. It just is too facile a tactic to be allowed to succeed.” 

Underwood v. Clark, 939 F.2d 473, 476 (7th Cir. 1991). Because of the ease of 

making such a claim and the waste of judicial resources that would occur if every 

defendant were entitled to a hearing by saying the magic words “my lawyer kept 

me off the stand,” pragmatic considerations require that someone other than the 

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defendant back up his story. See id. (holding that “some substantiation is 

necessary, such as an affidavit from the lawyer who allegedly forbade his client 

to testify” in order to “give the claim sufficient credibility to warrant a further 

investment of judicial resources in determining the truth of the claim.”). 

Second, even taking his version of events as true, he isn’t entitled to relief. 

With regard to Mr. Simon’s argument that his counsel was constitutionally 

ineffective for not preparing him to testify and not calling him as a witness, Mr. 

Simon asserts that: (1) he and his attorneys initially planned for him to take the 

stand; (2) his attorneys spent no time preparing him to testify; and (3) on the 

morning of the last day of trial, his attorneys told him they didn’t want to call 

him to testify and gave reasons. The decision about whether Mr. Simon would 

testify was his alone; his attorneys couldn’t have prevented him from testifying 

and couldn’t have forced him to testify against his will. To the extent that Mr. 

Simon is challenging not the decision to avoid calling him but rather the extent 

to which his attorneys prepared him for his testimony, whether they prepared 

him was irrelevant because he chose not to testify. Mr. Simon doesn’t assert in 

his affidavit or his § 2255 motion that the alleged inadequacy of the preparation 

influenced his decision not to take the stand, so whether his attorneys spent 

enough time going over his testimony with him is a moot point. 

Mr. Simon admits in his affidavit that his attorneys discussed the prospect 

of Mr. Simon testifying, and explained that having him testify would be a bad 

idea. He recalls them giving him two reasons for that recommendation: that the 

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trial judge “did not like” him and that if he testified he risked an obstruction of 

justice enhancement at sentencing. Accurate or not, those are exactly the kind 

of strategic considerations Strickland insulates from hindsight review. And there 

were many other excellent reasons his attorneys may have had for advising Mr. 

Simon not to take the stand. Chief among these was that a federal judge in a 

separate bankruptcy proceeding had made several formal findings that Mr. 

Simon’s testimony wasn’t credible. The trial court might have allowed the 

government to cross-examine Mr. Simon about those findings. See United States 

v. Dawson, 434 F.3d 956, 959 (7th Cir. 2006). Reasonable counsel could 

certainly have concluded that Mr. Simon’s testimony wasn’t worth the risk that 

the jury would hear about a federal judge essentially calling Mr. Simon a liar. 

The second facet of Mr. Simon’s claim – that he is entitled to relief because 

his attorneys never let him know that the decision to testify was his alone – fares 

no better. For one thing, it is belied by Mr. Simon’s own affidavit. He admits that 

his attorneys told him he had the right to testify. While he insists that he 

misinterpreted this statement (believing it meant that the government couldn’t 

prevent him from testifying, but his own lawyer still could), he doesn’t allege that 

his attorneys actually said anything that could be fairly construed as suggesting 

that interpretation. Mr. Simon’s attorneys can’t be blamed for assuming a client 

as educated and worldly as Mr. Simon would understand a clear statement in 

plain English that he had the right to testify. Mr. Simon also admits that on the 

last day of trial, his attorney asked him whether he would testify. Even if Mr. 

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Simon wrongly believed that he had no choice before that, the question alone 

should have sufficed to correct his thinking. Mr. Simon tries to explain why he 

didn’t infer from this question that the choice was his to make, but his 

explanations are too weak to warrant discussion. Even taking his affidavit as 

true, Mr. Simon’s attorneys said enough to put him on notice that it was up to 

him whether to testify in his own defense. 

Finally, failing to inform an client of the right to decide whether to testify 

doesn’t fall below an objective standard of reasonableness. Mr. Simon concedes 

in his motion that “[t]he Seventh Circuit has indicated that the failure to inform 

a defendant that the right to testify is his alone is not ineffective assistance of 

counsel.” He is correct. See Taylor v. United States, 287 F.3d 658, 661 (7th Cir. 

2002) (“There may be a factual dispute about whether counsel told [the 

defendant] in so many words that the accused alone makes the decision whether 

to testify, but this dispute is not material.”). Mr. Simon argues that other courts 

of appeal have held otherwise, and suggests that they take the better position. 

But the law of this circuit governs decisions by this court, and this court lacks 

the power to overrule opinions by the court of appeals. 

 Accordingly, Mr. Simon’s attorneys didn’t provide ineffective assistance 

regarding Mr. Simon’s decision whether to testify. Because Mr. Simon hasn’t 

identified any material factual dispute, he isn’t entitled to an evidentiary hearing. 

 III. CONCLUSION

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For these reasons, the court DENIES Mr. Simon’s § 2255 motion to vacate 

his sentence (Doc. No. 194). Moreover, because Mr. Simon hasn’t made a 

substantial showing of the denial of a constitutional right, the court declines to 

issue a certificate of appealability. See 28 U.S.C. § 2253(c). 

SO ORDERED. 

 ENTERED: July 5, 2016 

 /s/ Robert L. Miller, Jr. 

 Judge 

 United States District Court 

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