In the

United States Court of Appeals

For the Seventh Circuit

No. 09-1891

UNITED STATES OF AMERICA,

Plaintiff-Appellant,

v.

EDWARD R. VRDOLYAK,

Defendant-Appellee.

Appeal from the United States District Court

for the Northern District of Illinois, Eastern Division.

No. 07 CR 298—Milton I. Shadur, Judge.

ARGUED DECEMBER 10, 2009—DECIDED JANUARY 29, 2010

Before POSNER, MANION, and HAMILTON, Circuit Judges.

POSNER, Circuit Judge. Edward Vrdolyak pleaded

guilty to conspiracy to commit mail and wire fraud and

agreed in the plea agreement that the loss intended by

his fraud was between $1 million and $2.5 million. He

was sentenced to five years of probation, with a

community-service obligation but no confinement, and

to pay a $50,000 fine (a modest amount, because the

defendant has a high income, and a net worth in excess
2 No. 09-1891

of $1 million if his large loans to members of his family

are included). The government appeals, contending that

the judge miscalculated the sentencing-guidelines range

applicable to the defendant’s crime and committed other

errors. Although a judge is no longer required to give a

guidelines sentence, he is required to make a correct

determination of the guidelines sentencing range as the

first step in deciding what sentence to impose. Gall v.

United States, 552 U.S. 38, 50 (2007); United States v.

Gibbs, 578 F.3d 694, 695 (7th Cir. 2009).

The Chicago Medical School (as it was then known)

wanted to sell a property in Chicago that it owned consisting of a lot with a building on it. Stuart Levine was a

trustee of the medical school and the chairman of the

board’s real estate committee, and he agreed with the

defendant to use his position as a trustee to steer the

sale of the property to a buyer of the defendant’s

choice. The defendant lined up Smithfield Properties to

be the favored buyer in exchange for a $1.5 million fee

that Smithfield agreed to pay him, and he in turn agreed

to give Levine half the fee. The medical school was not

told about this corrupt arrangement. Levine like the

defendant has pleaded guilty to his part in the fraud

and has agreed not to contest a prison sentence of up to

67 months that the sentencing judge might impose.

Smithfield’s initial offer for the building—$9.5 million—was lower than two other potential buyers—the

Farley Group and Loyola University—were willing to

pay. The defendant advised Smithfield to up its offer, and

it did, to $15 million. Farley and Loyola remained inter-
No. 09-1891 3

ested in buying the property. To head them off, Levine

arranged for an “emergency” meeting of the medical

school’s board of trustees to consider offers for the property. At the meeting, although Farley had offered

$15 million and Loyola $15.5 million for the property,

the board, persuaded by Levine, decided to accept Smithfield’s offer and negotiate no further with Farley or

Loyola. The board discounted Loyola’s bid because

Loyola had not actually inspected the property before

bidding—Levine had seen to that. The board rejected

Farley’s bid because Levine strongly urged approval of

Smithfield’s bid, noting that Farley’s was lower because

it included a 4 percent brokerage fee that would be deducted from the amount paid to the school. This was

misleading, because Smithfield’s bid was contingent on

obtaining zoning approvals and Farley’s was not. And a

week later Farley upped its bid to $16 million, which

in pure dollar terms was higher than Smithfield’s even

after deduction of the brokerage fee. Farley was told that

it was too late.

The government was prepared to offer an affidavit

from Loyola’s broker that Loyola would have increased

its offer had it been given an opportunity to do so. And a

representative from Farley was prepared to testify that if

necessary Farley would have increased its offer to somewhere between $18 and $20 million. By convening the

emergency meeting Levine had made sure that Smithfield’s bid would be accepted and that he and the defendant would split the finder’s fee. Although we use “bid”

and “bidder” as synonyms for “offer” and “offeror,”
4 No. 09-1891

no formal auction was ever contemplated and so there

was no reason to consider Farley’s higher bid untimely.

The district judge concluded that the defendant’s fraud

had inflicted neither actual nor intended loss on the

medical school. His finding that it had inflicted no

actual loss was based on the fact that Smithfield’s bid was

the highest one considered at the “emergency” meeting.

The judge gave no weight to Farley’s week-later offer of

$16 million and refused to consider the evidence that

Farley would have bid $18 million to $20 million if

given the chance and that Loyola was also prepared to

offer more than $15.5 million. These rulings were erroneous. No emergency required the medical school’s board

of trustees to act with haste to award the sale contract.

The “emergency” was a ruse to preclude competition

with Smithfield.

The judge’s refusal to consider the evidence of what

Loyola or Farley would have done if given the chance to

sweeten their bids was based on his belief that uncommunicated intentions are unworthy of consideration by a

finder of fact. That is not correct. No rule of evidence

or principle of common sense makes a person’s testimony about his own intentions—testimony uniquely

based on his personal knowledge—inadmissible in a

sentencing proceeding any more than in any other proceeding in which intention is material. United States v.

Young, 247 F.3d 1247, 1252–53 (D.C. Cir. 2001). Who better

than a potential buyer knows what he would bid for a

property?

The judge himself speculated at the sentencing hearing

about the defendant’s uncommunicated intentions in
No. 09-1891 5

conspiring with Levine to defraud the medical school—

that he had acted out of friendship for Levine. A defendant’s testimony about his uncommunicated intentions

is no more credible than the testimony of an honest

third party about his uncommunicated intentions. To

believe the former and refuse even to listen to the

latter is error.

The weight to be given a piece of evidence is one thing,

and is ordinarily within the discretion of the trier of fact

to determine. Admissibility is another matter. A judge

is not permitted to have his own rules of admissibility—to

say for example that “[i]n my court no exceptions to the

hearsay rule will be recognized.” As we shall be emphasizing throughout this opinion, our concern is not with

the leniency of the defendant’s sentence as such but

with procedural errors committed by the judge en route

to the determination of the sentence.

The judge’s refusal to listen to the evidence of the

potential buyers was an egregious error because the

evidence was corroborated. The medical school’s

property had recently been appraised for $15 million on

the assumption that its best use was as a luxury

residential development, a use that would require

tearing down the building on the property. If the

building was not torn down (an expensive undertaking),

the land alone, according to the appraisal, was worth

$16.5 million. Loyola didn’t want to tear the building

down; it wanted to use it for student housing. It had

every reason therefore to offer more than Smithfield.

Farley had no intention of demolishing the building
6 No. 09-1891

either, and its intention to top Smithfield’s bid was corroborated by the $16 million offer that it made for the

property.

The judge was impressed by the fact that the defendant

had told Smithfield that $9.5 million was too low an

offer. By doing so, the judge reasoned, he had conferred

a benefit on the school. But that was not the defendant’s

intention. His intention was to make sure that Smithfield was the winning bidder, since the finder’s fee was

contingent on Smithfield’s getting the property. Whether

in an honest bidding process the school would have

obtained more than $15 million from Farley or Loyola or

perhaps from some other potential buyer can’t be determined with certainty because Levine prevented Farley

and Loyola from keeping the bidding going and prevented

everyone else who had expressed interest from even

making offers.

The judge thought the defendant’s interests perfectly

aligned with the school’s—thought that the more Smithfield bid, the more the school would receive, as well as the

defendant. That is not true. The defendant did want

Smithfield to be the high bidder, but he also wanted the

bidding process to be rigged, to make sure Smithfield

was the high bidder so that he would get his fee. The

result of the rigging was to prevent the medical school

from considering higher bids from Farley and Loyola

and perhaps others.

In determining pecuniary loss for purposes of calculating a sentencing-guidelines range, the judge is required

to determine the loss that the defendant “reasonably
No. 09-1891 7

should have known, was a potential result of the offense.” U.S.S.G. § 2B1.1, Application Note 3(A)(iv). That

potential loss in this case was the amount above

$15 million that another bidder might have decided to

pay for the property had the bidding been fair and open.

As an experienced lawyer and businessman, the

defendant must have known that a fair and open bidding

process might well yield a higher price than Smithfield

offered. In fact he knew that both Loyola and Farley

wanted to pay more than Smithfield, which made sense

because, as we said, both bidders wanted to use the

building on the property rather than tear it down.

The judge’s finding that the defendant had caused

no loss blocked the alternative measure of loss in cases

in which there is a loss but the precise amount of the

loss cannot be determined: in such a case the criminal’s

gain is treated as the measure of loss. U.S.S.G. § 2B1.1,

Application Note 3(B); United States v. Serpico, 320 F.3d

691, 698 (7th Cir. 2003); United States v. Bhutani, 266 F.3d

661, 668 (7th Cir. 2001); United States v. Chatterji, 46 F.3d

1336, 1340 (4th Cir. 1995). That makes good sense in

this case. Smithfield was willing to pay $1.5 million to

the defendant to obtain the property, and it must have

thought that if it didn’t pay that amount it would have

to up its bid by at least that much to win an unrigged

bidding contest. Only on that assumption did the kickback make sense from Smithfield’s standpoint. From the

defendant’s standpoint, the more Smithfield paid, the

better; but from Smithfield’s standpoint, the goal of

paying a finder’s fee was to enable Smithfield to obtain
8 No. 09-1891

the property for a smaller total outlay (price plus finder’s

fee) than it would have had to pay otherwise.

There was at the very least a probable loss, and that is

“loss” within the meaning of the guideline. United States v.

Johnson, 16 F.3d 166, 170 (7th Cir. 1994); United States v.

Schneider, 930 F.2d 555, 558 (7th Cir. 1991); United States v.

Stanley, 12 F.3d 17, 21 (2d Cir. 1993). It is true that cases

involving probable loss usually are ones in which the

illegal scheme is interrupted, so that its consequences

cannot be determined with certainty. Here it was not

interrupted. But the consequences still cannot be determined with certainty, and it would be even more anomalous to give the defendant a sentencing break when

there is no interruption by some outside force but

instead the very nature of the scheme precludes a

certain determination of loss.

The gain (and thus alternative measure of the loss) was

the $1.5 million finder’s fee. It is true that when

originally negotiated, the fee was contingent on certain

factors. But by the time of the defendant’s sentencing,

the contingencies had been dispelled and the defendant

would have been entitled, had the scheme not been

detected, to the full $1.5 million. That the fee was to be

split with a coconspirator is of no significance. U.S.S.G.

§ 1B1.3(a); United States v. Thomas, 199 F.3d 950, 952-54

(7th Cir. 1999); United States v. Boatner, 99 F.3d 831, 834-37

(7th Cir. 1996). Dividing the gain by the number of conspirators would mean that the larger the conspiracy,

the milder the punishment of each one. Anyway the

defendant stood to gain $750,000 from his crime—not a

negligible haul.
No. 09-1891 9

The zero loss found by the district judge created a

guidelines sentencing range of zero to six months in

prison; the correct loss figure of $1.5 million (which

incidentally was within the range that the defendant

agreed in the plea agreement was the intended loss attributable to his crime) ups the sentencing range to 33 to

41 months.

Ordinarily we would stop here and remand for

resentencing. But the judge went on to rule that if he was

wrong and there was a loss of $500,000, which would

create a guidelines range of 27 to 33 months in prison,

he would give the defendant a below-guidelines sentence of no prison—in fact the identical sentence that

he imposed on the assumption of zero loss.

But $500,000 was also error. And while a judge can

give a below-guidelines sentence, the sentence cannot

stand if it is based on a legal, factual, or analytic (connecting law and fact) error that is not harmless. The

court of appeals must “ensure that the district court

committed no significant procedural error, such as

failing to calculate (or improperly calculating) the Guidelines range, treating the Guidelines as mandatory, failing

to consider the § 3553(a) factors, selecting a sentence based

on clearly erroneous facts, or failing to adequately

explain the chosen sentence—including an explanation

for any deviation from the Guidelines range.” Gall v.

United States, supra, 552 U.S. at 51. “The allowable band

of variance [in sentencing] is greater after Booker than

before, but intellectual discipline remains vital.” United

States v. Kirkpatrick, 589 F.3d 414, 416 (7th Cir. 2009); see
10 No. 09-1891

also United States v. Peña-Hermosillo, 522 F.3d 1108, 1112

(10th Cir. 2008).

The judge committed three errors in his alternative

ruling. First, the $500,000 figure was erroneous for the

reasons we’ve given already. The correct figure was

$1.5 million and the guidelines range was therefore

higher than the judge thought. Second, repeating an

error in his computation of loss, the judge thought that

the defendant deserved leniency because he had

intended no harm to the medical school, but on the contrary had intended a benefit—that the school should

receive the highest bid from Smithfield. Notice the equivocation implicit in “highest bid from Smithfield.” The

highest bid from Smithfield is the bid that gets Smithfield the property; it is not the highest bid the seller

would have obtained had the bidding process not been

contaminated by the defendant’s kickback.

The judge’s third error was to give, without adequate

articulated consideration, enormous weight to letters

urging leniency for the defendant, while virtually

ignoring the evidence that tugged the other way. There

were 48 letters in all, some from members of the defendant’s family and others from persons for whom he had

done favors of a charitable nature, including gifts of

money.

The judge committed three errors en route to

deciding that the letters weighed more heavily in favor

of leniency than the defendant’s ethical violations as a

lawyer, pointed out by the government, weighed in

favor of severity. One error was his failure to discuss
No. 09-1891 11

any of the evidence that showed the defendant’s

character in a bad light. A sentencing judge is not

required to mention every bit of evidence presented in

the sentencing hearing, but an arbitrarily one-sided

commentary on the evidence raises a warning flag. The

judge did not remark the defendant’s discussing the

kickback scheme with Levine and telling him, “If two

fucking schemers like you and I can’t figure this out,

then we got a problem.” He did not mention the conspirators’ decision to evade taxes by the defendant’s

giving Levine’s wife a “loan” at a very high interest

rate with the understanding that that there was no obligation to repay; Levine’s cut would come from the loan.

He did not mention Ridge Chrysler Jeep, LLC v.

DaimlerChrysler Financial Services Americas LLC, 516

F.3d 623 (7th Cir. 2008), where our defendant assisted in

a fraud by litigants who had, we said, “behaved like a

pack of weasels.” Id. at 627. He did not mention the lie

that the defendant had told a district judge in 2002

when he was class counsel in a successful case and the

judge had asked him whether he would be collecting

any fees other than those set aside in a special

lawyer’s fund and he replied he would not—despite

collecting $150,000 from the named plaintiffs under

his contingency-fee agreement with them. The defendant

had a history of ethical misconduct to which the judge

without explanation gave negligible weight. Official

judgments of misconduct were discounted in favor of

letters procured by the defendant.

Second, the judge appears to have given no weight to

the fact that the defendant is by normal standards (not
12 No. 09-1891

Warren Buffett or Bill Gates standards) wealthy; his

annual income in recent years has sometimes exceeded

$1 million. Wealthy people commonly make gifts to

charity. They are to be commended for doing so but

should not be allowed to treat charity as a get-out-of-jail

card. United States v. Repking, 467 F.3d 1091, 1095-96 (7th

Cir. 2006) (per curiam); United States v. Ali, 508 F.3d 136,

149 (3d Cir. 2007); United States v. Cooper, 394 F.3d 172, 176-

77 (3d Cir. 2005). As the court in Repking put it (quoting

Cooper), “charitable works must be exceptional before

they will support a more-lenient sentence, for . . . ’it is

usual and ordinary, in the prosecution of similar whitecollar crimes involving high-ranking corporate executives . . . to find that a defendant was involved as a leader

in community charities, civic organizations, and church

efforts.’ ” 467 F.3d at 1095. People “who donate large

sums because they can should not gain an advantage

over those who do not make such donations because

they cannot.” United States v. Thurston, 358 F.3d 51, 80

(1st Cir. 2004), vacated on other grounds, 543 U.S. 1097

(2005); cf. United States v. Stefonek, 179 F.3d 1030, 1038

(7th Cir. 1999). “To allow any affluent offender to point

to the good his money has performed and to receive a

downward departure from the calculated offense level on

that basis is to make a mockery of the Guidelines.

Such accommodation suggests that a successful criminal

defendant need only write out a few checks to charities

and then indignantly demand that his sentence be reduced. The very idea of such purchases of lower sentences

is unsavory, and suggests that society can always

be bought off, even by those whose criminal misconduct
No. 09-1891 13

has shown contempt for its well-being.” United States

v. McHan, 920 F.2d 244, 248 (4th Cir. 1990).

Third, the judge ignored the fact that the defendant

was for many years an influential Chicago alderman.

Politicians are in the business of dispensing favors; and

while gratitude like charity is a virtue, expressions of

gratitude by beneficiaries of politicians’ largesse should

not weigh in sentencing. See United States v. Wright,

363 F.3d 237, 248-49 (3d Cir. 2004); United States v. Serafini,

233 F.3d 758, 773 (3d Cir. 2000); cf. United States v. Morken,

133 F.3d 628, 630 (8th Cir. 1998).

We are not laying down rules of sentencing. The sentencing discretion of federal judges is broad and our

concern is not with the judge’s having taken account of

the defendant’s good works but with his failure to

consider the full range of evidence pertinent to a just

sentence. That was an error, just like the judge’s erroneous calculation of the applicable guidelines sentencing range. Appellate review of errors committed in

sentencing is plenary. Gall v. United States, supra, 552 U.S.

at 51; United States v. Gibbs, supra, 578 F.3d at 695 (“we

review the procedures followed by the district court

de novo”). Review turns deferential when the issue is the

substantive reasonableness rather than the procedural

regularity of the sentencing determination. The cascade

of errors and omissions that we have identified cannot

be dismissed as harmless, and so requires that the defendant be resentenced.

And in fairness to the government, which is entitled to

the same consideration as other litigants, the resentencing

should be by a different judge. (The government did not
14 No. 09-1891

ask us to order the case remanded to a different

judge; repeat litigants—litigants who expect to appear

before the same judge in the future—are for obvious

reasons reluctant to request such relief. We commonly

issue such orders, as we are authorized by our Circuit

Rule 36 to do, without a request by a litigant.) One

cannot read the 168-page transcript of the sentencing

hearing, and the two memoranda attempting to justify

the sentence that the judge issued after he had

announced the sentence at the conclusion of the hearing,

without sensing that the judge had committed himself irrevocably to a noncustodial sentence for the defendant. He pretty much announced this at the outset of the

hearing, and he repeatedly expressed his anger with the

government’s lawyers over matters that did not warrant

anger, such as the government’s reference to the fraud

as having been conducted by “insiders” (plural—Levine

and the defendant). The judge said that Levine was

indeed an insider by virtue of being a member of the

fraud victim’s board of trustees but that the defendant

was not, and he excoriated the government’s lawyer for

calling him an insider. But all the lawyer had meant

was that the defendant is a prominent “insider” in the

Chicago, legal, business, and political communities. For

the lawyer had merely said “I will use the term insider

for Mr. Vrdolyak, in the sense of someone who is connected in this City to people who are in power.” And the

judge kept hectoring the government’s lawyers about

what he viewed as their misunderstanding of the real

estate business; but we cannot fathom what that misunderstanding was.
No. 09-1891 15

Despite patient explanation by the government’s lawyers, the judge would not waver in his conviction that

the defendant had acted with the best interests of the

medical school in mind—which is untrue because the

school’s interest was to have an honest bidding process

and the defendant knew it—and that the defendant had

acted out of friendship for Levine, who had financial

problems. (That was the Robin Hood defense.) The defendant could have assisted Levine financially without

defrauding a medical school. Given the defendant’s

prominence, his affluence, and his professional status as

a lawyer, his crime was especially gratuitous. When

Levine asked for assistance in defrauding the medical

school, the defendant did not hesitate and was quickly

able to find a company willing to pay the kickback. He

did not cooperate with the government in the investigation of the crime and did not plead guilty until the eve

of trial.

The gratuity of the crime suggests that there can be no

assurance that if let off with a slap on the wrist, the defendant will not commit a future crime. He has lost his law

license, but the crime of which he has been convicted did

not require a law license. He did not benefit from

the crime—but only because he was caught.

The judge’s errors in calculating the guidelines range

are indicative of an idée fixe that the defendant was not to

receive a custodial sentence, even (as the government

urged in the alternative) home confinement. In United

States v. Peña-Hermosillo, supra, 522 F.3d at 1117, the Tenth

Circuit held that “impos[ing] the same sentence under
16 No. 09-1891

an alternative rationale” had been a “procedural error,”

explaining that “it is hard for us to imagine a case where

it would be procedurally reasonable for a district court

to announce that the same sentence would apply even

if correct guidelines calculations are so substantially

different, without cogent explanation. In the absence of

explanation, we might be inclined to suspect that the

district court did not genuinely ‘consider’ the correct

guidelines calculation in reaching the alternative rationale.” Id. See also our decision in United States v.

Anderson, 517 F.3d 953, 965-66 (7th Cir. 2007), where

we expressed concern with “blanket” sentences.

The judgment is reversed and the case remanded for

resentencing before a different judge, pursuant to 7th

Cir. Rule 36. We intimate no view on what a proper

sentence would be.

REVERSED AND REMANDED.

HAMILTON, Circuit Judge, dissenting. I agree that the

district court erred in the guideline loss calculation, but

I respectfully dissent because that error was harmless.

The record shows an experienced district judge considering a difficult case thoroughly and exercising his

discretion reasonably under 18 U.S.C. § 3553(a) to craft a

sentence to fit both the crime and the criminal. The error
No. 09-1891 17

in the guideline calculation did not affect the final

decision, and I find no abuse of discretion in the final

decision about the sentence.

As the majority explains, given the nature of Vrdolyak’s

and Levine’s crime, it is more accurate to say that there

was a loss that cannot be determined reliably than to

say that there was no loss to the victim of the crime.

Where the crime makes it so difficult to determine with

confidence the amount of the loss, the guidelines and

cases from this and other circuits establish that the intended gain for the conspirators is a useful substitute

for loss in applying the guidelines to gauge the severity

of the crime. Application Note 3(B) to U.S.S.G. § 2B1.1

provides: “The court shall use the gain that resulted

from the offense as an alternative measure of loss only

if there is a loss but it reasonably cannot be determined.”

That approach has been used, for example, in United

States v. Briscoe, 65 F.3d 576, 589-90 & n.16 (7th Cir. 1995)

(affirming sentence of union president who defrauded

union through kickback scheme with lender to union

members; loss calculation based on defendant’s gain), as

well as in United States v. Vinyard, 266 F.3d 320, 332 (4th

Cir. 2001) (affirming sentence in kickback scheme based

on defendant’s gain), and United States v. Yeager, 331

F.3d 1216, 1224-26 (11th Cir. 2003) (affirming sentence

based on defendant’s gain through scheme to divert

drug sales through unauthorized dealers at lower prices).

But the guideline calculation is only the beginning of

the story, for both the district court and this court. Pursuant to United States v. Booker, 543 U.S. 220, 259-60 (2005),
18 No. 09-1891

after calculating the applicable sentencing guideline

range, the district court was required to look beyond the

guidelines and to consider the case under 18 U.S.C.

§ 3553(a). Congress has instructed:

The court shall impose a sentence sufficient, but not

greater than necessary, to comply with the purposes

set forth in paragraph (2) of this subsection.

Paragraph (2) of subsection (a) requires the court to

consider:

the need for the sentence imposed—

(A) to reflect the seriousness of the offense, to promote

respect for the law, and to provide just punishment for the offense;

(B) to afford adequate deterrence to criminal conduct;

(C) to protect the public from further crimes of the

defendant; and

(D) to provide the defendant with needed educational

or vocational training, medical care, or other

correctional treatment in the most effective manner. . . .

18 U.S.C. § 3553(a). The district court was required to

consider the guidelines, but it was prohibited from presuming that a guideline sentence would be a reasonable

sentence. Rita v. United States, 551 U.S. 338, 351 (2007).

At the end of the lengthy sentencing hearing in this

case, the district judge addressed the factors and purposes under section 3553(a). He explained how and why

he had concluded that a sentence of five years’ probation
No. 09-1891 19

(which was above the guideline range he calculated),

plus 2500 hours of community service and a fine, was

sufficient but not greater than necessary to serve those

purposes. The defendant committed a serious crime, but

there were a number of factors that the district court

could and did consider in mitigation. The defendant is

71 years old, had no prior criminal record, and posed

little risk of repeat offenses. He had given up his law

license. The crime of fraud did not involve violence,

and there was no element of public corruption. The

defendant had agreed to help a friend by committing

the crime, but he was not the instigator of the crime

and did not actually benefit from it. The district court

was also impressed by a surprising volume of information showing the defendant’s character was very different from his public image in the media. That information showed generosity with time, money, and influence

to help people in need, especially where the defendant

had no moral or other obligation to help them and

where he received no publicity or recognition for his

kindnesses. That is not the entire picture, of course, but

those are all factors that could reasonably lead the district court to exercise its discretion under section 3553(a)

to impose the sentence that it did. See Gall v. United

States, 552 U.S. 38, 48-49 (2007) (affirming belowguideline sentence of probation and recognizing substantial restrictions on liberty imposed by sentence

of probation).

Under Booker and Gall the district court is required to

calculate the applicable sentencing guidelines for the

crime and the criminal, and an error in the calculation is
20 No. 09-1891

a procedural error in sentencing that may require a remand. Booker, 543 U.S. at 259-60; Gall, 552 U.S. at 49-51.

At the same time, however, it is clear that errors in calculating the advisory guideline calculations are subject

to harmless error analysis. E.g., United States v. Abbas,

560 F.3d 660, 666-67 (7th Cir. 2009) (holding guideline

error was harmless); United States v. Anderson, 517 F.3d

953, 965-66 (7th Cir. 2008) (same); see generally Williams

v. United States, 503 U.S. 193, 203 (1992) (stating before

Booker that guideline errors were subject to harmless

error analysis). In both Abbas and Anderson, the district

courts recognized the disputed guideline issues, stated

that their sentences would be the same regardless of

how the guideline issues were decided, and provided

thoughtful explanations of their reasoning. In such cases,

because the sentencing guidelines are no longer mandatory, appellate courts should readily find that guideline

errors are harmless.

Correct application of the guidelines can present many

difficult or esoteric questions, including many that have

little to do with the ultimate legal and moral judgment

about an appropriate sentence. Since Booker, this court

has often recognized that the sentencing judge may

impose a reasonable sentence under section 3553(a)

regardless of how a difficult guideline issue might be

resolved. “When a judge proceeds in this manner, she

must make clear that the § 3553(a) factors drive the sentence without regard as to how the prior conviction

fits under a particular guideline. Doing so will make the

often nit-picking review of issues like this under our

now advisory guideline scheme unnecessary.” United
No. 09-1891 21

States v. Sanner, 565 F.3d 400, 406 (7th Cir. 2009) (affirming

above-guideline sentence without regard for correct

resolution of guideline issue); Abbas, 560 F.3d at 666-67

(finding that district court erred in guideline calculation but holding error was harmless based on judge’s

explanation of alternative basis for same sentence).

In this case, the judge considered the relevant factors

thoughtfully and made his intentions and reasons clear.

The precise level of loss in the judge’s alternative guideline calculation did not drive the final decision.

As Abbas and Anderson make clear, this is not to say

that a district court can insulate any sentence from appellate review by saying a few magic words about

section 3553(a). Abbas, 560 F.3d at 666-67; Anderson,

517 F.3d at 965; accord, United States v. Peña-Hermosillo,

522 F.3d 1108, 1118 (10th Cir. 2008) (finding guideline

error was not harmless where district court provided

only “perfunctory” explanation for alternative rationale);

see generally United States v. Williams, 431 F.3d 767, 773-

76 (11th Cir. 2005) (Carnes, J., concurring) (encouraging

district courts to provide alternative sentencing rationales

where resolution of disputed guideline issues would not

affect sentences). But where the record shows that the

district court considered the disputed guideline issue,

considered the prospect that its decision on the issue

might be wrong, and provided a thoughtful explanation

of its reasons under section 3553(a), it should be

relatively easy to find that an error in calculating an

advisory guideline was harmless, as I believe this one

was. In some important respects, this case provides a
22 No. 09-1891

mirror-image of United States v. Spano, 476 F.3d 476 (7th

Cir. 2007), a public corruption case in which the district

court imposed a sentence on one defendant that was

substantially higher than the proper guideline range. The

district court imposed an upward departure of four

levels for extraordinary abuse of trust, and this court

held that the decision was an error. We found that the

error was harmless, however, because the judge explained why he thought a guideline sentence that

did not take into account the egregious abuse of trust

would not be adequate. Despite the guideline error, we

upheld the above-guideline sentence as a proper and

sensible exercise of the district court’s discretion under

section 3553(a). Id. at 480-81. In this case involving

private corruption, the district court imposed a sentence below the correct guideline range, but with a reasonable exercise of that same discretion.

The majority identifies three reasons why the loss

calculation error should not be deemed harmless and

concludes further that the case should be remanded to

another district judge under Circuit Rule 36 to ensure the

government a fair hearing. In my view, the criticisms

here are not warranted, and the government received a

fair hearing before the district court.

First, the majority criticizes the district court for basing

the alternative sentencing rationale on the assumption

that the guideline loss could have been no higher than

$500,000, which would put the sentencing guideline

range two offense levels lower than the correct range
No. 09-1891 23

The correct guideline calculation starts with a base offense 1

level of 6 under U.S.S.G. § 2B1.1(a)(2), adds 16 levels under

§ 2B1.1(b)(1)(I) for a loss of more than one million dollars,

and subtracts two levels for acceptance of responsibility under

§ 3E1.1(a), for a total offense level of 20. With Vrdolyak’s

criminal history category of I, the sentencing guideline range

is 33 to 41 months in prison. Using a loss of $500,000, the

district court assumed an upward adjustment of 14 and a total

offense level of 18, with a guideline range of 27 to 33 months

in prison.

here. The district court’s thorough discussion of the 1

factors relevant to sentencing under section 3553(a)

showed that the two-level difference would not have

made any difference in the court’s ultimate decision, so

the error in calculating the loss under the guidelines

had no effect. The sentencing range that is 14 levels

below level 20 (the correct level) is the same as the

range that is 14 levels below the level 18 the district court

considered as its alternative—zero to six months in

prison. And in fact, though we reach the conclusion

from opposite directions, the majority and I agree

that there is no point in remanding the case to

Judge Shadur for a new guideline calculation and imposition of the same sentence as before. Where the majority

sees a “cascade of errors and omissions,” I see just one

harmless error in the advisory guideline calculation.

Second, the majority criticizes the district court for

believing the defendant intended no harm to the

medical school and actually intended to benefit it by

arranging for the highest bid from Smithfield. This criti-
24 No. 09-1891

cism does not accurately reflect the record. On the first

point, the district court pointed out correctly that there

was no evidence that the defendant intended to hurt the

medical school, see Gov’t App. at 25, and the government itself had submitted evidence showing that the

defendant had wanted Smithfield to pay “top dollar” for

the property. See Def. Reply Mem. at 8 (quoting recorded

conversation on March 31, 2006). The district court necessarily recognized, however, that the defendant must

have realized that his help for his friend Levine would

hurt the medical school by distorting the sale process

in favor of the corrupt side deal to benefit Levine and

the defendant. That’s why the defendant is guilty.

That’s why the district court accepted his plea of guilty.

On the second point, the furthest the district judge

went was to note several times that the defendant’s

“finder’s fee” (10 percent of the purchase price, to be

split with Levine) would go up as Smithfield’s

purchase offer went up. Gov’t App. 21-22, 25. I do not

find in the record any indication that the district judge

thought that the defendant, who had pled guilty to a

serious crime and whom he was sentencing for that

crime, acted with the intent to benefit the medical

school. The district judge understood how Levine and

Vrdolyak had corrupted the sale process—Vrdolyak had

pled guilty, after all.

Third, the majority criticizes the district court for

giving too much weight to numerous letters urging

leniency in sentencing while giving too little weight to

information that hurt the defendant’s cause. On this

topic, the majority identifies three more specific errors:
No. 09-1891 25

failing to discuss adequately the information weighing

against the defendant, failing to consider the

defendant’s wealth and its effect on his ability to show

mitigating good works, and ignoring the defendant’s

earlier work as an influential Chicago alderman.

These criticisms are not warranted. The record shows

that the district court gave careful and discriminating

consideration to the mitigating and aggravating information. The letters in mitigation came from the

defendant’s family and friends, and from others who

described ways in which the defendant had helped

them over the years. The district judge said that those

letters were an “extraordinary outpouring that’s not

matched—at least in my recollection—in any other

case that I have had coming up to be 29 years on the

bench.” Gov’t App. 76.

Like victim impact statements, such letters are

entirely appropriate in a sentencing hearing. Cf. Gall,

552 U.S. at 43 (affirming below-guideline sentence of

probation where district court relied in part on “small

flood” of letters from family, friends, neighbors, and

business associates). The district court has an obligation

to consider such letters when considering the history

and characteristics of the defendant. See 18 U.S.C.

§ 3553(a)(1). Such letters often add little to the relevant

picture of the defendant and his crime, but sometimes

they can provide unexpected information and add new

insights into the defendant’s character.

This was such a case. The veteran district judge was

surprised by what he learned. Like almost everyone
26 No. 09-1891

who has lived in Chicago over the past three or

four decades, the judge had been generally aware of the

reputation of “Fast Eddie” Vrdolyak, leader of the opposition to Mayor Harold Washington and power broker in

Chicago politics. The judge did his best to put aside

those preconceptions and to approach the sentencing

decision with an open mind. He explained candidly:

When I first encountered the case, and throughout

its pendency, I never expected that I was going to

reach the destination that I find called for here. And

as I have indicated, I had (as I suspect anybody who

has seen the political environment in Chicago over a

long time frame probably shared) a perception of our

defendant today that I suppose is epitomized by

the moniker “Fast Eddie,” indeed from the so-called

Council Wars that existed during the Harold Washington mayoralty.

Gov’t App. 135-36. In explaining that he would have

reached the same result regardless of the guideline loss

calculation, the judge said:

In any event, the point I think that is most important

is that when I applied 3553(a) I would reach the

same result whichever of those views [about loss

under the guidelines] is taken. And that’s because

I again surprised myself in terms of how I looked at

this thing coming in, with the absence of a full appreciation or full understanding or disclosure of

what the thing involved. I would not have dreamed

of imposing a noncustodial sentence. But I have got

to tell you that when you look at the 3553(a) factors,
No. 09-1891 27

it seems to me that the reasonable result, the one

that is called for taking all of the considerations

into account, is just what I have indicated.

Id. at 138. These frank observations of the judge—about

the ways in which the facts overcame the defendant’s

public reputation and persuaded the judge to reach a

result he had not expected to reach—deserve substantial

weight.

Contrary to the majority’s criticisms about failing to

consider the defendant’s wealth and influence, the

district judge was discriminating in weighing the letters

about the defendant’s character. During the defense

presentation, the judge commented:

I am not sure that things that are done for family

members carry—or for that matter for what’s called a

public persona carries—much weight. At least as I read

these letters, the thing that I found frankly most persuasive

on his part were the things that were not visible, and things

in which at least according to these people he reached out

in situations where he need not have done so. He had no

obligation to do that either morally or otherwise and did it

anyway. And that’s frankly the reason that I characterized the letters that I received—not simply in terms of

volume, but in terms of impact—as giving the kind

of astonishingly different portrayal than what you

have characterized as public persona.

Gov’t App. 93 (emphasis added).

The most important mitigating information here involved not the “checkbook charity” that can be easy for
28 No. 09-1891

“But, surely, if ever a man is to receive credit for the good

2

he has done, and his immediate misconduct assessed in the

context of his overall life hitherto, it should be at the moment

of his sentencing, when his very future hangs in the balance.

This elementary principle of weighing the good with the bad,

which is basic to all the great religions, moral philosophies,

and systems of justice, was plainly part of what Congress had

in mind when it directed courts to consider, as a necessary

sentencing factor, ‘the history and characteristics of the defendant.’ ” United States v. Adelson, 441 F. Supp. 2d 506, 513-14

(S.D.N.Y. 2006), aff’d mem., 301 Fed. Appx. 93 (2d Cir. 2008).

the wealthy, but many instances in which the defendant

provided hands-on help in long-term relationships with

people in need, or where he provided generous help

anonymously. The district judge’s comments show that

he was much more impressed by these many instances

of the defendant’s generosity and kindness with his

time and influence in situations where there was no

visibility or public reward for his actions.2

Even with the appropriate discounting desired by the

majority, the letters still have unusual persuasive

weight, and the district court was not required to ignore

or discount the evidence of past good works. The majority’s observation that wealthy defendants should not

get a break compared to poor ones merely because

they have given away some of their wealth is certainly

true but misses the district court’s real point in

weighing this mitigating information.

The majority writes that the district court “ignored the

fact that the defendant was for many years an
No. 09-1891 29

The letters of Dr. Mark Siegler and others described several 3

instances in which the defendant intervened to enable needy

people to obtain live-saving medical care that was not otherwise available to them. See Def. Ex. N (Siegler). The letter of

Jonathan Kleinbard, a former vice president of the University

of Chicago, told of a case in which Vrdolyak represented a

plaintiff suing the University of Chicago Medical Center for

medical malpractice. Vrdolyak failed in his effort to settle the

(continued...)

influential Chicago alderman.” Slip op. at 13. This fact is

relevant, the majority asserts, because politicians are in

the business of dispensing favors, so that later expressions of gratitude for politicians’ largesse should not

be given weight in a sentencing decision. This criticism

is not warranted. The defendant left public office more

than 20 years ago, long before most of the events cited in

mitigation. His history in Chicago politics and public

life certainly did not escape the district judge’s notice.

The district judge’s comment quoted above—discounting

letters about things the defendant had done for his “public

persona”—shows that the district court was quite conscious of precisely the point the majority faults him for

ignoring. See also Gov’t App. 137 (court referring to “the

extraordinary volume and character of the things that

I received in support of Mr. Vrdolyak, the kinds of

thing that the public persona would never have

dreamed existed, and I certainly not”). In other words,

the letters that impressed the court most were those

addressing private actions that were not designed to

help the defendant himself, in his private or public life.3
30 No. 09-1891

(...continued) 3

case with Kleinbard’s help, and he eventually won a judgment

“in the millions of dollars.” Kleinbard reported that Vrdolyak

then donated his entire legal fee to the University of Chicago

Medical Center. Def. Ex. Z. 

The majority criticizes the district court for not saying

more about evidence putting the defendant’s character

in a bad light. The district court showed that it was

familiar with the evidence the government had

submitted, including the incidents cited from the defendant’s legal career. The court acknowledged the “substantial information that’s unfavorable to Vrdolyak” and

said it was reminded of Dr. Jekyll and Mr. Hyde, as

defense counsel urged a sentence for Dr. Jekyll and the

government urged a sentence for Mr. Hyde. Gov’t App. 76.

The court specifically asked the defense to address the

lawyer disciplinary matters, id. at 127, and the defense

provided explanations that offered at least some

mitigating effect. Id. at 128-29. Criticism of the district

court for having failed to say more about these

events, which had been the subject of two censures and

one short suspension from practice, demands too

much from an oral sentencing explanation.

Based on what is described as a “cascade of errors and

omissions,” the majority orders a remand under Circuit

Rule 36 to another district judge for a fresh look at the

sentence. I see instead just one harmless error, and I do not

believe the government was denied a fair hearing. The

majority concludes that Judge Shadur “had committed

himself irrevocably to a noncustodial sentence for the
No. 09-1891 31

defendant.” Slip op. at 14. The majority criticizes the

judge for having announced this view near the outset of

the sentencing hearing, before the government had a

chance to argue for a custodial sentence. This criticism

is off target for two reasons.

First, it fails to acknowledge how much work the

parties and the district court had put into the sentencing decision before the hearing itself. In detailed

written briefs, the parties had set forth their positions on

the guideline issues, the section 3553(a) factors, and the

sentence that would be appropriate. The district judge’s

comments throughout the sentencing hearing show that

he fully understood the parties’ positions from the outset. Having done such extensive preparation, it would have

been unusual for the judge not to have had a good idea

how he intended to sentence the defendant, and why, at

the beginning of the sentencing hearing.

 Second, the fact that the judge signaled his informed

inclinations early in the hearing does not call for criticism.

Most lawyers appreciate knowing more rather than less

about the judge’s thinking while there is still an opportunity to persuade the court. This criticism is no more

warranted than would be criticism that an appellate

judge had a view of the case at the beginning of an

oral argument. Such views do not mean that minds are

closed to further persuasion by probative evidence and

legal argument. See also Gov’t App. 76-77 (district court

inviting views and stating “I really have not reached a

conclusion”). Judges must keep their minds open to

new information that will change their thinking, as the

district judge did in this case. And where the majority
32 No. 09-1891

The majority criticizes the district court for refusing to 4

consider after-the-fact evidence from other interested buyers

about how much more they would have been willing to offer

for the property. I see no abuse of discretion in the district court’s decision not to spend time on the government’s

speculative effort to show the likely result of an honest

effort to have sold the property for the best available price.

finds in the record a district judge who was without

justification impatient and angry with the government,

I find a frank and wide-ranging discussion of the issues

in the case, and some reasonable annoyance with overly

aggressive arguments and invitations to speculate.

4

Perhaps the most remarkable thing about the way this

case has proceeded on appeal is that the government’s

briefs did not challenge the reasonableness of the

sentence or ask for remand to a different judge. In its

opening brief, the government argued only the guideline loss error. The government did not even bother to

mention the district court’s alternative guideline calculation and analysis under 18 U.S.C. § 3553(a). Where the

district court has stated such an alternative basis, we

should treat the appellant’s silence as at least a

forfeiture of the issue. And it is hard to believe that the

government’s approach to this appeal was not carefully

considered in every respect. We would be justified in

finding a waiver based on the government’s failure to

address the alternative calculation and its failure to

challenge the reasonableness of the sentence.

Finally, although it is evident that the majority views

the sentence here as simply not heavy enough to punish
No. 09-1891 33

this crime adequately, we should not overlook an important dimension of this sentence that may in the end be

more powerful than a shorter prison term. The idea of a

person as prominent as Ed Vrdolyak doing 2500 hours

of community service in Chicago has elements of public

shaming and service that were well within the district

court’s discretion in deciding how best to accomplish

the purposes of sentencing with a sentence “sufficient,

but not greater than necessary,” as section 3553(a) directs. It is hard to imagine that this defendant’s community service could be completed without considerable

news media attention, which would add to the

deterrent effect of that portion of the sentence.

In sum, the record here shows that an experienced

judge considered the case thoughtfully and learned

information that overcame his initial inclinations in the

case (and many public reactions to the case). The judge

exercised his discretion under section 3553(a) and

imposed a sentence reasonably tailored to fit both the

crime and the criminal. Though the majority and I

disagree with the district judge on the loss calculation

under the advisory sentencing guidelines, that error was

harmless because it did not drive the final sentencing

decision under section 3553(a). I would affirm the

district court’s judgment.

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