          United States Court of Appeals
                     For the First Circuit


No. 14-2228

                    UNITED STATES OF AMERICA,

                            Appellee,

                               v.

                         JOHN S. ALPHAS,

                      Defendant, Appellant.


          APPEAL FROM THE UNITED STATES DISTRICT COURT

                FOR THE DISTRICT OF MASSACHUSETTS

         [Hon. Douglas P. Woodlock, U.S. District Judge]



                             Before

                    Barron, Selya and Stahl,
                         Circuit Judges.



     Tracy A. Miner, with whom Megan A. Siddall and Demeo LLP were
on brief, for appellant.
     Brian A. Pérez-Daple, Assistant United States Attorney, with
whom Carmen M. Ortiz, United States Attorney, was on brief, for
appellee.



                           May 7, 2015
            SELYA, Circuit Judge.           When a criminal defendant is

convicted   of    a   fraud    offense,    the   Sentencing    Commission   has

established amount of loss — generally the higher of actual or

intended loss — as a rough proxy for determining the seriousness of

the offense and the relative culpability of the offender. Although

this concept is easily stated, its application often has vexed

sentencing courts.      As in so many other instances, the devil is in

the details.

            This appeal requires us to decide two issues of first

impression in this circuit.           The first involves the method for

calculating the guideline enhancement for amount of loss in an

insurance fraud context.           The second involves the method for

calculating the amount of statutory restitution in that context.

Concluding, as we do, that the court below erred in adopting its

calculation methods, we vacate the appellant's sentence and remand

for resentencing.

I.   BACKGROUND

            Because this sentencing appeal follows a guilty plea, we

distill the pertinent facts from the plea agreement, the change-of-

plea   colloquy,      the     undisputed    portions   of     the   presentence

investigation report (PSI Report), and the transcript of the

disposition hearing.        See United States v. Almonte-Nuñez, 771 F.3d

84, 86 (1st Cir. 2014).




                                      -2-
             Defendant-appellant John S. Alphas owns and operates The

Alphas Company, a wholesale produce distributor located in Chelsea,

Massachusetts.        During the relevant time frame, the appellant

purchased     large    quantities   of     produce,   often   from   distant

purveyors.     To protect his investment, the appellant routinely

obtained insurance on these produce shipments.

             In or around March of 2007, the appellant devised a

scheme to defraud.        Over the next four and one-half years, he

submitted at least ten fraudulent claims to his insurers for lost,

stolen, or damaged produce.1        The appellant sought reimbursement

for the value of allegedly lost, stolen, or damaged produce,

together with disposal expenses, shipping fees, and the cost of

procuring replacement stock.        These claims were largely bogus: in

each instance, the appellant either invented fictitious losses or

artificially inflated legitimate losses. To make matters worse, he

supported his submissions with documents that had been fraudulently

altered or, in some cases, constructed out of whole cloth.               He

compounded his mendacity by making false and misleading statements

to insurance adjusters.

             The insurance policies at issue contained void-for-fraud

clauses.    A representative clause stated:


     1
       Nine of these claims were submitted to Zurich North American
and the final claim to Selective Insurance Company. Though all of
the claims were submitted in the name of The Alphas Company, the
sentencing context requires us to attribute those claims and the
underlying losses to the appellant.

                                     -3-
           This Coverage Part is void in any case of
           fraud by you as it relates to this Coverage
           Part at any time. It is also void if you or
           any other insured, at any time, intentionally
           conceal or misrepresent a material fact
           concerning:

           1.   This Coverage Part;
           2.   The Covered Property;
           3.   Your interest in the Covered Property; or
           4.   A claim under this Coverage Part.

           Four of the appellant's claims were never paid: three

were   withdrawn    after   suspicions   surfaced   and   the   lone   claim

submitted to Selective Insurance Company was thwarted by early

detection of the fraud. The other six claims were paid, but mostly

in amounts less than their face value.          In sum, the ten claims

totaled over $490,000, yet the appellant received payments totaling

only $178,568.41.

           The appellant's persistent pattern of chicanery sparked

a federal criminal investigation.        In May of 2014, the government

filed an information charging the appellant with a single count of

wire fraud.        See 18 U.S.C. § 1343.       Waiving prosecution by

indictment, the appellant pleaded guilty to the charge.                In an

accompanying plea agreement, the parties stipulated to a base

offense level of 7.     See USSG §2B1.1(a)(1).

           The parties could not agree, however, as to the amount of

loss — a necessary step in determining the guideline sentencing

range (GSR).       To fill this void, the PSI Report recommended

boosting the appellant's offense level by 14 levels based on an


                                   -4-
intended loss of approximately $480,000.               See id. §2B1.1(b)(1)(H)-

(I) (increasing offense level by 14 for losses exceeding $400,000

but not greater than $1,000,000).                This calculation derived from

the probation officer's conclusion that intended loss should be

measured by the face amount of the appellant's claims, less a $1000

per claim deductible.

              The appellant objected to the recommendation.               He argued

that the loss figure should exclude legitimate losses embedded in

the fraudulent claims.           In conjunction with this argument, he

submitted a competing set of calculations that purported to show

which component amounts were legitimate.               This set of calculations

yielded      an    intended   loss    amount      of   roughly    $178,000      which

corresponded to an increase of 10 (rather than 14) in his adjusted

offense level.       See id. §2B1.1(b)(1)(F).

              The    PSI   Report     also    dealt    with    restitution.        It

recommended an award of $178,568.41 (the aggregate amount actually

paid   out    on    the    claims).        The   appellant     objected    to    this

recommendation,       envisioning      a     finding   of     actual    loss    (and,

therefore, a restitution amount) of $58,931.36.                  Once again, the

appellant attributed the reduced figure to the fact that a portion

of the claims paid corresponded to legitimate losses.

              The probation officer stood by her calculations regarding

both the guideline enhancement and restitution.                        Although she

conceded that the appellant may have incurred legitimate losses,


                                           -5-
she maintained that the appellant's fraud rendered the claims

altogether illegitimate.

             The disposition hearing was held on November 6, 2014.

The district court concluded as a matter of law that where, as

here, insurance policies contain void-for-fraud clauses, intended

loss is equal to the aggregate face value of the claims submitted.

Starting with this premise, the court overruled the appellant's

objections; enhanced his offense level by 14 levels; deducted 3

levels for acceptance of responsibility, see id. §3E1.1; placed the

appellant in Criminal History Category I; and set the GSR at 27 to

33 months, see id. Ch.5, Pt.A, sentencing table.                  The court then

varied     sharply    downward,    sentencing      the      appellant       to   an

incarcerative term of 12 months and 1 day.           In addition, the court

fined the appellant $60,000; attached a 36-month term of supervised

release;     and   ordered   payment     of   restitution    to    Zurich    North

American in the amount of $178,568.41.

             This timely appeal ensued. The district court refused to

stay the appellant's sentence pending appeal. This court, however,

granted a stay. See United States v. Alphas, No. 14-2228 (1st Cir.

Dec.   31,   2014)    (finding    that    appeal   presented       "'substantial

question' within the meaning of 18 U.S.C. § 3143(b)(1)(B)").

II.    ANALYSIS

             The appellant assigns error to the district court's

determination of the amount of loss with respect to both the


                                       -6-
guideline enhancement and the award of restitution.            Because these

determinations     are    controlled     by   different    authorities,      we

bifurcate our analysis.

                     A.   The Guideline Enhancement.

            The appellant first contends that the sentencing court

used an improper method of calculating intended loss and, thus,

erred in enhancing his offense level by 14 levels. This contention

is met at the threshold by the government's assertion that we need

not reach the merits because any calculation error was harmless.

We begin with that assertion and then proceed to the merits.

            1.     Harmlessness.        The   government's     argument      for

harmlessness rests on the district court's imposition of a below-

the-range sentence coupled with the court's later remark, made

while denying the appellant's motion to stay the sentence pending

appeal, that a recalculation of the GSR would be unlikely to result

in   a   lower   sentence.    This     argument   flies   in   the   teeth   of

conventional wisdom, which teaches that the improper calculation of

a defendant's guideline range comprises a significant procedural

error.    See Gall v. United States, 552 U.S. 38, 51 (2007).           Such an

error ordinarily requires resentencing.             See United States v.

Ramos-Paulino, 488 F.3d 459, 463-64 (1st Cir. 2007).                 Indeed, a

defendant normally can appeal from an error in calculating his GSR

even though the district court imposed a sentence beneath the




                                     -7-
bottom of the GSR.   See United States v. Paneto, 661 F.3d 709, 715

(1st Cir. 2011).

            To be sure, an appellate court may deem such an error

harmless if, after reviewing the entire record, it is sure that the

error did not affect the sentence imposed.          See Williams v. United

States, 503 U.S. 193, 203 (1992).        In other words, resentencing is

required if the error either affected or arguably affected the

sentence.   See Ramos-Paulino, 488 F.3d at 463.

            The case at hand does not fit within these narrow

confines.   Although the court below imposed a sentence beneath the

bottom of the GSR, there is at least a possibility that the court

would have imposed an even more lenient sentence had it started

with a lower GSR.    See United States v. Foley, ___ F.3d ___, ___

n.13 (1st Cir. 2015) [Nos. 13-1048, 13-1118, slip op. at 31 n.13].

While the court stated that a lower GSR was "unlikely" to result in

a   different   sentence,   we   have    recently   reaffirmed   that   the

possibility of a lesser sentence is enough to preclude a finding

that an error in calculating the GSR is harmless.          See id.   Such a

possibility exists here: saying that an event is unlikely is not

the same as a categorical assurance that the event will not come to

pass.   It follows that if the court below erred on the high side in

fashioning the guideline enhancement for amount of loss (and, thus,

the GSR), we cannot regard that error as harmless.




                                   -8-
          2.   Calculating Intended Loss.           Our rejection of the

government's harmlessness argument brings us to the merits of the

appellant's claim that the district court committed a calculation

error.    We   review   de   novo   the   court's    interpretation   and

application of the sentencing guidelines, including the propriety

of its loss-computation method.      See United States v. Prange, 771

F.3d 17, 35 (1st Cir. 2014); United States v. Walker, 234 F.3d 780,

783 (1st Cir. 2000).

          In fraud cases like this one, the guidelines direct the

sentencing court to augment the defendant's offense level based on

the amount of loss. See USSG §2B1.1(b)(1). For this purpose, loss

is defined as "the greater of actual loss or intended loss."          Id.

§2B1.1, comment. (n.3(A)).      Here, the district court based its

guideline calculation on intended loss.            That term means "the

pecuniary harm that was intended to result from the offense."         Id.

at n.3(A)(ii). Intended loss is not synonymous with probable loss.

Rather, the term "includes intended pecuniary harm that would have

been impossible or unlikely to occur."       Id.     Seen in this light,

intended loss "is a term of art meaning the loss the defendant

reasonably expected to occur at the time he perpetrated the fraud."

United States v. Innarelli, 524 F.3d 286, 290 (1st Cir. 2008).

This standard focuses primarily on the offender's objectively

reasonable expectations, see id., though subjective intent may play




                                    -9-
some role, see id. at 291 n.6; United States v. McCoy, 508 F.3d 74,

79 (1st Cir. 2007).

          In this case, the sentencing court concluded that the

intended loss was equal to the aggregate face value of the claims

submitted by the appellant to his insurers, not the aggregate

amount by which the appellant fraudulently inflated those claims.2

The court reasoned that had the insurers known of the fraud when

they received the claims, they would have invoked the void-for-

fraud clauses and paid nothing.     The court did not explain what

bearing the void-for-fraud clauses may have had on the amount of

loss that the appellant intended to cause.    It said only that if

intended loss were to be viewed solely as the amount of fraudulent

inflation, fraudsters would have an incentive to inflate claims

because, if caught in the act, they would be punished only for the

inflated amount.

          The government applauds this reasoning, but the appellant

decries it.   He notes that the sentencing guidelines treat loss as

a proxy for relative culpability.   In his view, basing an intended

loss computation on the entire amount of an insurance claim rather

than on the amount fraudulently claimed irrationally conflates the




     2
        We express no opinion on whether any portion of the
appellant's claims was legitimate. This is a matter the district
court will need to address on remand. See text infra. For present
purposes, we assume — as the appellant contends — that he did
suffer some legitimate losses.

                                -10-
culpability    of   fraudsters         who       commit   significantly    different

offenses.

            Fraud has many manifestations, and calculating the loss

associated with a particular scheme is sometimes more art than

science.    As a result, we have eschewed rigid rules and instead

taken "a pragmatic, fact-specific approach" to loss calculation.

Prange, 771 F.3d at 35 (internal quotation mark omitted).                     Such a

pragmatic view suggests that loss computation should distinguish

between an outright swindler who peddles, say, a forged title to a

bridge in Brooklyn and a fraudster who contrives to render some

value (albeit less than promised) to the victim.                     See id. at 36;

United States v. Blastos, 258 F.3d 25, 30 (1st Cir. 2001).                     By any

practical measure, the former seems more culpable than the latter.

            Applying       the   degree-of-culpability             approach   to   the

insurance fraud context, it is appropriate for the loss-computation

method to distinguish between a fraudster who wholly fabricates a

non-existent claim and a fraudster who artificially inflates a

legitimate claim.      A fraudster who has suffered no loss at all but

invents a $100,000 claim out of thin air is not the same as a

fraudster     who   has     suffered         a    legitimate     $50,000   loss    but

artificially inflates his claim to $100,000.                    See United States v.

Smith, 951 F.2d 1164, 1167 (10th Cir. 1991).

            This    gets    to   the    heart       of    the   matter.    Under   the

sentencing guidelines, loss generally does not include sums that a


                                         -11-
victim would have paid to the defendant absent the fraud.                      See,

e.g., United States v. Evans, 155 F.3d 245, 253 (3d Cir. 1998)

(holding that actual loss in insurance fraud case does not include

value of legitimate claims); United States v. Parsons, 109 F.3d

1002, 1004 (4th Cir. 1997) (same, in context of government benefits

fraud); see also United States v. Miller, 316 F.3d 495, 498-99 (4th

Cir. 2003) (applying this principle to intended loss).               Given this

rule, the question reduces to whether the presence of a void-for-

fraud clause makes a dispositive difference when calculating loss

under the sentencing guidelines.

            In resolving this question, we find instructive the line

of cases involving government benefits fraud.                    When a person

fraudulently     obtains    government      benefits,     the    United       States

typically   is   entitled    to   recover    all   sums   paid    (in     a    civil

forfeiture proceeding) even though some benefits would have been

paid anyway (that is, absent the fraud).                See, e.g., 5 U.S.C.

§ 8148(a); 28 U.S.C. § 2514.       But when the same fraudulent conduct

undergirds a criminal conviction, courts have steadfastly refused

to equate the amount of loss under the sentencing guidelines with

the amount recoverable by the government through civil forfeiture.

That is because "[f]orfeiture is a penalty imposed on a criminal

independent of any loss to the crime victim." Parsons, 109 F.3d at

1005.   Consequently, "[t]he loss itself (whether the actual or

intended loss) is limited to the tangible economic loss of the


                                    -12-
victim."    Id. at 1004.    The forfeitable amount does not count

toward the government's loss, which is measured by the amount of

benefits that was (and, in the case of intended loss, would have

been) paid as a result of the fraud.    See United States v. Harms,

442 F.3d 367, 380 (5th Cir. 2006); United States v. Dawkins, 202

F.3d 711, 715 (4th Cir. 2000).

            To be sure, government benefits fraud is governed by a

special application note, which explains that in such cases loss

"shall be considered to be not less than the value of the benefits

obtained by unintended recipients or diverted to unintended uses."

USSG §2B1.1, comment. (n.3(F)(ii)).     We believe that this note

merely represents a specialized application of the guidelines'

general focus on a defendant's relative culpability.    See, e.g.,

Dawkins, 202 F.3d at 714; Parsons, 109 F.3d at 1004-05. Since this

is so, it makes good sense to transplant the reasoning of the

government benefits cases to the analogous context of insurance

fraud.

            We discern no sound basis for treating a void-for-fraud

clause (in the insurance fraud context) differently than a civil

forfeiture (in the benefits fraud context).     Both the void-for-

fraud clause and the civil forfeiture anodyne afford relief after

the fact.    So, too, such a clause, like the sword of Damocles

inherent in a threat of civil forfeiture, serves the salutary

purpose of encouraging transactional honesty.   And such a clause,


                                 -13-
like a civil forfeiture, imposes a penalty on the fraudster for

acting corruptly: if the insurer discovers the fraud, the insured

forfeits everything.

            The concept of loss under the sentencing guidelines

serves a completely different purpose.             See United States v.

Hamaker, 455 F.3d 1316, 1337 (11th Cir. 2006); Dawkins, 202 F.3d at

715.     The guidelines are designed to ensure that the sentence

imposed on a defendant "reflect[s] the nature and magnitude of the

loss caused or intended by [his] crimes."           USSG §2B1.1, comment.

(backg'd.).       Consonant with this design, the guidelines use amount

of loss as the primary metric by which "the seriousness of the

offense and the defendant's relative culpability" are measured.

Id.    Sums forfeited under a void-for-fraud clause (which is really

nothing    more    than   an   after-the-fact   penalty)   do   not   conform

naturally to this metric.          Cf. id. §2B1.1, comment. (n.3(D)(i))

(providing that "loss" does not include "[i]nterest of any kind,

finance charges, late fees, penalties, amounts based on an agreed-

upon return or rate of return, [and] other similar costs").                It

would therefore be anomalous to read the guidelines to distinguish

between two fraudsters who fraudulently inflate their claims by

exactly the same amount simply because one is covered by an

insurance policy that contains a void-for-fraud clause and the




                                     -14-
other is covered by an insurance policy that does not contain such

a clause.3

             The government resists this reasoning, asseverating that

the appellant intended to deprive his insurers of the entire amount

claimed   regardless    of   whether    some   portion   of   that   amount

represented legitimate losses.         To achieve this counterintuitive

result, the government asks us to consider what an objectively

reasonable fraudster standing in the appellant's shoes would have

expected to be paid were the fraud discovered.            Because such a

fraudster would be aware of the void-for-fraud clauses and know

that the misrepresentation would relieve his insurers of their

payment obligation, the government's thesis runs, the fraudster

would expect his insurers to suffer losses in the full amount of

the submitted claims.

             We reject the government's thesis, which approaches

intended loss from the wrong angle. Fraudsters do not expect to be

found out but, rather, expect to reap the benefits of their

contrivance.     The relevant inquiry, then, is what the fraudster

reasonably expected to euchre out of his victim, cf. id. at



     3
       We base this conclusion on the language and purpose of the
sentencing guidelines, not the language of the particular policies
at issue. Whether and to what extent an insurance contract is void
or voidable is often a thorny issue and we do not need to resolve
that issue here. For the reasons discussed above, an insurer's
loss for guideline purposes is distinct from any recovery to which
it might be entitled under a void-for-fraud clause in a civil
proceeding.

                                  -15-
n.3(A)(ii) (defining "intended loss" as "the pecuniary harm that

was intended to result from the offense" (emphasis supplied)), not

what would have slipped through his fingers had he been caught in

the act.

           That   amount   necessarily   excludes   any   sums   that   the

fraudster would have been paid absent the fraud.          See Burrage v.

United States, 134 S. Ct. 881, 887-88 (2014) (explaining that the

phrase "results from" implies "a requirement of actual causality,"

which typically "requires proof that the harm would not have

occurred in the absence of — that is, but for — the defendant's

conduct" (internal quotation marks omitted)).             The sentencing

court, then, should have determined whether and to what extent

legitimate claims were embedded in the fraud.

           Structuring "intended loss" in this way makes good sense.

After all, loss is meant to serve as a proxy for the seriousness of

the crime and the relative culpability of the offender.          The best

way to gauge the seriousness of a fraud offense is to determine how

much the fraudster set out to swindle — and no fraudster sets out

to swindle sums that he would have been paid anyway.        That is also

the best way to gauge a fraudster's culpability.

           The best case for the government's contrary position is

United States v. Torlai, 728 F.3d 932 (9th Cir. 2013) — but Torlai




                                  -16-
cannot carry the weight that the government loads upon it.4             Torlai

involved a defendant who had obtained crop insurance policies from

private insurers through a federal program.               See id. at 935-36.

Those policies and their application documents included void-for-

fraud clauses.     See id. at 940 & n.8.       The defendant made a number

of misrepresentations both when he procured the policies and when

he submitted claims under them.         See id. at 936, 941-43.

            Appealing his sentence, the defendant argued that the

district court erred in calculating loss by failing to determine

which portions of his indemnity claims were legitimate.              The Ninth

Circuit disagreed, noting that the case involved a government

benefits program and, therefore, loss constituted "the value of the

benefits obtained by unintended recipients."             Id. at 938 (emphasis

omitted) (quoting USSG §2B1.1, comment. (n.3(F)(ii))).               The court

stated that "[b]y virtue of his fraud, [the defendant] was not

eligible for any government benefit under the crop insurance

program, and therefore, he was not an 'intended beneficiary.'" Id.

at 943.

            Certain     facts     underlying    the   court's    "unintended

beneficiary" rationale help to distinguish Torlai from this case.

First,    the   Ninth   Circuit    found    sufficient    evidence   that   the



     4
       The government's citation to United States v. Ostrom, 80 F.
App'x 67 (10th Cir. 2003), need not detain us. That decision lacks
precedential force even in the circuit of its origin. See 10th
Cir. R. 32.1(A).

                                     -17-
defendant had suffered no reimbursable losses, see id. at 941-43,

so he would not have received anything absent his fraudulent

claims.   Second, the defendant made material misrepresentations to

procure the crop insurance policies, see id., making it unlikely

that the insurer would have issued the policies had it been told

the truth.    This latter fact indicates that, regardless of the

legitimacy vel non of the claimed losses, the insurer would not

have been obliged to pay.    Cases in which an insurer would have

paid nothing absent the fraud are materially different from those

in which the insurer would have paid something (but less than the

full amount claimed) absent the fraud.       See United States v.

Sharma, 703 F.3d 318, 324-25 (5th Cir. 2012).5

           To recapitulate, we conclude that the district court

erred in calculating the amount of intended loss attributable to

the fraud and, thus, in fashioning the guideline enhancement.   We

are, therefore, constrained to remand for resentencing. On remand,

the district court should compare what the appellant sought to

bamboozle his insurers into paying with what they would have paid

had the appellant submitted only bona fide claims.

           We add a coda. It is apodictic that the government bears

the burden of proving the applicability of a sentencing enhancement

by preponderant evidence.   See Paneto, 661 F.3d at 715.   But in a


     5
       To the extent that Torlai can be read to support the
position advocated by the government here, we decline to adopt its
reasoning.

                                -18-
case such as this — where a defendant's claims were demonstrably

rife with fraud — a sentencing court may use the face value of the

claims as a starting point in computing loss. See United States v.

Campbell, 765 F.3d 1291, 1304-05 & n.13 (11th Cir. 2014); United

States v. Hebron, 684 F.3d 554, 562-63 (5th Cir. 2012). The burden

of production will then shift to the defendant, who must offer

evidence to show (if possible) what amounts represent legitimate

claims. See Hebron, 684 F.3d at 563; United States v. Jimenez, 513

F.3d 62, 86 (3d Cir. 2008).        After the record is fully formed, the

sentencing court must determine the amount of loss that the

government    (which    retains    the   burden   of   proof)   is   able   to

establish.        The court, however, "need only make a reasonable

estimate of the loss."            USSG §2B1.1, comment. (n.3(C)); see

Blastos, 258 F.3d at 30.          Depending on the defendant's offer of

proof, the court might well conclude that the amount of loss is

equal to the face value of the submitted claims.

                       B.   The Restitution Order.

             The appellant further contends that the district court

erred in calculating restitution.           The government counters both

that this claim is waived and that it is impuissant.

             1.    Purported Waiver.     Waiver typically occurs when a

party intentionally relinquishes a known right.          See United States

v. Rodriguez, 311 F.3d 435, 437 (1st Cir. 2002). In the sentencing

context, an appellant may waive an issue when he initially raises


                                     -19-
it as an objection to the PSI Report but later explicitly withdraws

the objection.    See United States v. Eisom, 585 F.3d 552, 556 (1st

Cir. 2009); Rodriguez, 311 F.3d at 437.         Once an issue is waived,

there is nothing for an appellate court to review.            See Rodriguez,

311 F.3d at 437.

             Here, the appellant challenged the loss computation both

in objections to the PSI Report and in his sentencing memorandum.

His objection was directed to the calculation of both the guideline

enhancement and the restitution award. A common thread ran through

both halves of his argument: loss simply does not include amounts

that   the   victim   would   have   paid   absent   the   fraud.    At   the

disposition hearing, the appellant's trial counsel forcefully

presented this argument in connection with the calculation of the

guideline enhancement.        The court rejected it.          Later on, the

appellant's counsel was asked whether he wanted the court to

consider any other modifications to the PSI Report.                 Counsel

responded in the negative.

             The sentencing proceeding continued.          At one point, the

court remarked that it did not understand the amount of restitution

to be disputed and asked defense counsel whether he was looking at

the same set of numbers.       Counsel responded that he was.

             The government urges us to find that these (and similar)

statements amounted to an intentional relinquishment of the right

to contest the amount of restitution.          This exhortation has some


                                     -20-
superficial appeal: taken in a vacuum, the sentencing colloquy can

be read as an acknowledgment that the appellant was not pressing

any arguments about the amount of restitution.     It surely would

have been better practice for counsel to have clarified that he had

no objections to the restitution amount save for the method of

calculation (that is, the court's announced unwillingness to deduct

any legitimate portions of the claims from the loss calculation).

But reading the sentencing transcript as a whole, we do not think

that defense counsel's statements clear the high bar needed for a

finding of waiver.

          Waivers are strong medicine, see Pike v. Guarino, 492

F.3d 61, 72 (1st Cir. 2007), and that medicine should not be

dispensed in criminal cases where ambiguity lurks, see United

States v. Bradstreet, 207 F.3d 76, 79-80 (1st Cir. 2000).    On this

scumbled record, defense counsel's statements, taken in the context

of the sentencing hearing as a whole, were ambiguous.       The main

event at sentencing was the battle over the method of calculating

loss.6   Having lost that battle after a full airing, counsel's

statements can fairly be read as an acknowledgment that the court's

arithmetic (though not its method of calculation) was correct with

respect to restitution.   Any other reading would be illogical: it


     6
       Although the district court specifically addressed the
method of calculation only in connection with the guideline
enhancement, its reasoning plainly encompassed restitution as well.
Indeed, the government, both before us and in the court below, has
made identical arguments concerning the two issues.

                               -21-
would have been odd for the appellant to press his computational

argument    to   the   bitter    end    with       respect   to   the    guideline

enhancement and then impliedly abandon the very same argument with

respect to restitution.

            The short of it is that there was no waiver.                   Defense

counsel's statements are most sensibly read as a recognition that

the critical issue already had been decided against his client, not

as a concession of that issue.

            As a fallback, the government suggests that the appellant

forfeited    the   restitution     issue      by    not   raising   it     at   the

disposition hearing, thus engendering review for plain error.                   See

Rodriguez, 311 F.3d at 437.             This argument is fruitless: the

appellant raised the issue in written objections to the PSI Report

and in his sentencing memorandum, and his attorney presented a

legal basis for the argument to the sentencing court.                   No more was

exigible to avoid a finding of forfeiture.                See United States v.

Theodore, 468 F.3d 52, 58 (1st Cir. 2006).

            2.     Amount.      The district court ordered restitution

pursuant to the Mandatory Victims Restitution Act (MVRA), 18 U.S.C.

§ 3663A.    Since the appellant's challenge to the restitution order

is based on an alleged error of law, our review is plenary.                     See

United States v. Cutter, 313 F.3d 1, 6 (1st Cir. 2002); see also

Walker, 234 F.3d at 783 (explaining that proper method of loss

computation is "a prototypical question of legal interpretation").


                                       -22-
           The MVRA authorizes a court to award restitution only in

the amount of a victim's actual loss.     See Innarelli, 524 F.3d at

294-95.   Thus, the question boils down to whether the presence of

the void-for-fraud clauses in the insurance policies converts the

entire amount paid in response to the appellant's claims into an

actual "loss."

           The answer depends, in relevant part, on the MVRA's

definition of a victim as a "person directly and proximately harmed

as a result of the commission of an offense for which restitution

may be ordered."7    18 U.S.C. § 3663A(a)(2).        Mindful of this

definition, we have held that, under the MVRA, a court may only

order restitution for losses that have an adequate causal link to

the defendant's criminal conduct.      See Cutter, 313 F.3d at 7.

           Importantly, we have made it pellucid that "restitution

should not be ordered if the loss would have occurred regardless of

the defendant's misconduct."   Id.     This means that the government

must establish a but-for connection between the defendant's fraud

and the victim's loss.   See United States v. Vaknin, 112 F.3d 579,

590 (1st Cir. 1997) (interpreting parallel provision in Victim and

Witness Protection Act, 18 U.S.C. § 3663).      Our case law on this



     7
       Because the appellant's offense of conviction involves, as
an element, a "scheme or artifice to defraud," 18 U.S.C. § 1343,
victims include those "directly harmed by the defendant's criminal
conduct in the course of the scheme," id. § 3663A(a)(2).      This
language does not alter the direct causation requirement.      See
United States v. Hensley, 91 F.3d 274, 277 (1st Cir. 1996).

                                -23-
point is consistent with the weight of authority under the MVRA.

Actual loss is widely (and correctly) thought to be limited to

pecuniary harm that would not have occurred but for the defendant's

criminal activity.      See, e.g., Sharma, 703 F.3d at 324; United

States v. Petruk, 484 F.3d 1035, 1038 (8th Cir. 2007); United

States v. Feldman, 338 F.3d 212, 220-21 (3d Cir. 2003); Dawkins,

202 F.3d at 715.

             Applying the MVRA and the case law interpreting it, we

think   it   evident   that   the   district   court   erred   in   ordering

restitution in the full amount paid to the appellant simply because

the insurance policies included void-for-fraud clauses. While such

clauses may suffice to ground claims for disgorgement in civil

proceedings, an insurer's recoverable loss for MVRA purposes is

confined to the amount the insurer would not have paid but for the

fraud. See United States v. Chalupnik, 514 F.3d 748, 754 (8th Cir.

2008); Petruk, 484 F.3d at 1038-39.

             This gets the grease from the goose.       The appellant has

contended all along that some portion of his claims represented

legitimate losses.     This remains to be proven.      But if it is true,

Zurich North American presumably would have reimbursed him for

those losses had he presented them without embellishment.                The

district court must, therefore, reconsider its restitution order,

taking into account the extent (if at all) to which the appellant's




                                    -24-
claims encompassed legitimate losses.8        The district court need

only make "a reasonable determination of appropriate restitution by

resolving uncertainties with a view towards achieving fairness to

the victim."       United States v. Burdi, 414 F.3d 216, 221 (1st Cir.

2005) (internal quotation marks omitted).

III.       CONCLUSION

               We need go no further. For the reasons elucidated above,

we vacate the appellant's sentence (including the restitution

order) and remand for resentencing consistent with this opinion.

On remand, the only issues open to consideration shall be the

appropriate amount of intended loss for purposes of the guideline

enhancement, the appropriate amount of actual loss for purposes of

restitution, and, of course, the dimensions of the sentence to be

imposed.



Vacated and Remanded.




       8
       The appellant alternatively suggests for the first time      on
appeal that if the void-for-fraud clauses dictate the amount        of
loss, the restitution award should be offset by the amount          of
premiums paid. Given our holding, we do not have any occasion       to
consider this alternative suggestion.

                                   -25-
