Of the Federal Circuit, sitting by designation. *

United States Court of Appeals

For the First Circuit

No. 06-2185

UNITED STATES OF AMERICA,

Appellant,

v.

GARY JAMES MILO,

Defendant, Appellee.

APPEAL FROM THE UNITED STATES DISTRICT COURT

FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Nancy Gertner, U.S. District Judge]

Before

 Boudin, Chief Judge,

Torruella and Dyk, Circuit Judges. *

Jennifer Hay Zacks, Assistant United States Attorney, with

whom Michael J. Sullivan, United States Attorney, was on brief for

appellant.

Robert L. Sheketoff for appellee.

October 30, 2007
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BOUDIN, Chief Judge. This is an appeal by the government

contesting the sentence imposed by the district court on Gary Milo.

Milo was arrested in 2003 for trafficking in marijuana. He

thereafter agreed to plead guilty and assist the government in

pending investigations. The government in turn agreed, subject to

getting substantial cooperation, to file a motion for a reduced

guideline sentence, U.S.S.G. § 5K1.1, and a sentence below the

mandatory minimum, 18 U.S.C. § 3553(e) (2000).

On April 29, 2004, Milo pled guilty to a sealed one-count

information alleging conspiracy to possess with intent to

distribute and to distribute marijuana in violation of 21 U.S.C. §

846 (2000). The information described Milo's role in heading a

large-scale marijuana distribution operation in Massachusetts,

spanning four years and involving "1,000 kilograms or more" of

marijuana. Forfeiture of Milo's proceeds from the operation was

sought as well. 21 U.S.C. § 853. 

As is common in such cases, sentencing was deferred while

Milo assisted investigators. In May 2006, the cooperation having

been completed, the probation officer prepared the pre-sentence

report, and the government filed its promised motion. The PSR

found Milo accountable for over 6,000 kilos of marijuana; it found

that the conspiracy had been an extensive one involving five or

more participants; and it found that Milo himself had directed at

least two individuals to transport marijuana or drug proceeds. It
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also noted that while under supervision Milo had tested positive

for cocaine on one occasion.

Milo, born in 1955, was described in the PSR as having

been brought up in an upper middle class home, although it said

that he had suffered some abuse. He was married, had attended but

not graduated from college and had learned building design from his

father. He had a builder's license and a realtor's license and had

worked in both fields and estimated his income (apart from drugs)

at $50,000 a year. His estimated net worth slightly exceeded $2.5

million. 

The PSR calculated the mandatory minimum sentence as 10

years, 21 U.S.C. § 841(b)(1)(A)(vii), and the guidelines range as

151 to 188 months. The calculation reflected a base offense level

of 34 premised on the 6,000 kilos and no prior criminal history.

An upward three-level adjustment for role in the offense matched an

equal reduction for acceptance of responsibility. U.S.S.G. §§

3B1.1(b), 3E1.1. Milo objected that the kilo amount was

overstated; the probation officer said that it did not affect the

calculation.

In its promised motion, the government described Milo's

cooperation in a number of different investigations. The

government moved both for relief from the mandatory minimum, 18

U.S.C. § 3553(e), and from the otherwise applicable guideline

sentence, U.S.S.G. § 5K1.1, and proposed to recommend a sentence of
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75 months, approximately half of the guideline minimum as

calculated by the probation officer.

Letters were submitted by those who knew Milo. They

described him (with detailed examples) as a caring and decent

person, helpful to others; set forth his work since his arrest for

Habitat for Humanity and other charitable endeavors; attested to

his contrition; expressed confidence that he would never repeat his

crime; and, in many cases, expressed hope that he would not have to

serve time in prison.

At sentencing, Milo's experienced counsel said he had

seen few examples of such complete remorse and urged that Milo be

given no time in prison. The prosecutor agreed that Milo had done

"a great job" and helped the government "in significant and

important ways." But, she said, Milo had brought thousands of

pounds of marijuana into the district over a number of years, and

75 months was a "generous" reduction from the ordinary guideline

sentence.

After Milo spoke, expressing contrition and saying that

he had sought to turn his life around, the district court said that

it would accept defense counsel's recommendation. The judge

referred without elaboration to Milo's "extraordinary" cooperation

and the force of the letters in the record and said that the 18

days already spent by Milo in detention and the prospect of a very

large forfeiture yet to be computed counted as punishment.
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The court then sentenced Milo to time served, five years

of supervised release with the first six months to be served in a

community corrections facility, and a fine of $50,000. Thereafter,

in denying a government motion for reconsideration, the district

court rejected any suggestion that the government should have been

surprised by the sentence and elaborated on what the court said was

already in the record before the sentencing hearing:

The sentencing concerned the extraordinary

nature of Mr. Milo's cooperation as described

in the government's presentation. But it also

concerned the extent to which Mr. Milo had

changed his life, the steps he had taken in

his work, steps which effectively increased

the amount of money the government was likely

to recover on forfeiture, and his exemplary

work with Habitat for Humanity.

In discussing the government's objections, the court said

that the Milo sentencing was about contrition as well as

cooperation; that many defendants bargain and cooperate as a kind

of "business arrangement" but that Milo was genuinely remorseful

and "had changed his life (addressing his addictions, working for

Habitat for Humanity, etc.)." The court referred briefly to the

large forfeiture judgment expected. It agreed with defense counsel

that Milo was "someone who the Court will never see again."

The government has now appealed to this court, arguing

primarily that the sentence is unreasonably low: specifically, that

"the district court sentenced a major marijuana dealer to timeserved . . . an 18-day term of imprisonment" even though Milo
The Supreme Court's recent decision in Rita v. United States, 1

127 S. Ct. 2456 (2007) (holding that a presumption of

reasonableness may be accorded to a sentence within the guidelines

range) has no bearing on this case. Two cases are currently

pending in the Supreme Court involving appellate review of district

court departures from the Sentencing Guidelines. Gall v. United

States, No. 06-7949 (argued October 2, 2007); Kimbrough v. United

States, No. 06-6330 (argued October 2, 2007).

The PSR calculated a total offense level of 34 based in part 2

on Milo's distribution of between 3,000 and 10,000 kilos of

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participated in an extensive four-year drug conspiracy yielding him

almost $10 million. The government also attacks various of the

district court's statements in support of the sentence as without

support or resting upon factors not properly considered.

We review sentences primarily for reasonableness, United

States v. Booker, 543 U.S. 220, 261 (2005), asking whether the

district court offered "a plausible explanation" and reached "a

defensible overall result." United States v. Jimenez-Beltre, 440

F.3d 514, 519 (1st Cir. 2006) (en banc), cert. denied, 127 S. Ct.

928 (2007). Embedded factual findings in the sentencing

determination are reviewed for clear error, United States v. MislaAldarondo, 478 F.3d 52, 70 (1st Cir.), cert. denied sub nom.,

Aldarondo v. United States, ___ S. Ct. ___, 2007 WL 1647161 (Oct.

1, 2007), while claims of strictly legal error are reviewed de

novo. United States v. Smith, 445 F.3d 1, 4 (1st Cir. 2006).1

The government says that it is of no moment whether the

proper guideline sentencing range was 87-108 (as the district court

said) or 151-188 (as the PSR found). Either range calls for a 2
marijuana. U.S.S.G. § 2D1.1(c)(3). Apparently because Milo only

admitted in the plea agreement to "over 1,000 kilograms" of

marijuana, the court set the offense level at sentencing as 32,

U.S.S.G. § 2D1.1(c)(4), yielding a range of 121-151 months. Then,

the court used level 29, equating to a range of 87-108. The

written judgment seemingly arrived at 29 by ignoring the threelevel enhancement for role in the offense.

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multi-year sentence and, without a motion, the statutory mandatory

minimum would be 10 years; the sentence imposed amounts to almost

no time in prison. The main question posed by the government's

appeal is the adequacy, given circumstances and the court's

explanation, of such a sentence for a major drug crime that is

ordinarily heavily punished by a sentence of 10 to 15 years.

Three subsidiary government arguments warrant brief

attention. The first is that the district court improperly relied

on the large forfeiture order (ultimately $9.9 million), which by

statute must be imposed "in addition to any other sentence

imposed." 21 U.S.C. § 853(a) (emphasis added); see also 18 U.S.C.

§ 3554. But the statute does not say that the forfeiture can never

be considered by the district court in determining the overall

sentence, and here the forfeiture was calculated on estimated

proceeds (not profits) and so has punitive characteristics. 

At the same time, one could hardly give the forfeiture in

this case much weight. Given his net worth of $2.5 million, Milo

may never be able to pay the full forfeiture. And if Milo had

independent means, avoiding a prison sentence on this account would

create an appearance that financially successful criminals can buy
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their way out of prison. See United States v. Mueffelman, 470 F.3d

33, 40 (1st Cir. 2006); cf. United States v. Tom, ___ F.3d ___,

2007 WL 2822908 at *5-6 (1st Cir. Oct. 1, 2007). The district

court did not rely heavily on the forfeiture, mentioning it only

briefly, and we see no error in the district court's apparent

decision to afford some minor weight to it.

Second, the government argues that the district court

gave undue emphasis to Milo's charitable activities. These are a

discouraged factor under the Sentencing Guidelines which provide:

"Military, civic, charitable, or public service; employment-related

contributions; and similar prior good works are not ordinarily

relevant in determining whether a departure is warranted."

U.S.S.G. § 5H1.11. The government does not claim this reliance to

be impermissible but merely to contribute to the unreasonableness

of Milo's sentence.

Again, the district court did not place much weight on

these activities to justify by themselves a lower sentence.

Rather, the activities (which began after Milo's arrest and were

real but not extraordinary) appear mainly to have bolstered the

court's judgment that Milo had turned his life around, was

genuinely and not just conveniently contrite and would not reoffend. This is perhaps an evidentiary use of post-arrest good

works to show rehabilitation and colorably a legitimate inference,
Previous decisions have said that little weight should be 3

given to the charitable contributions of business leaders who "are

often expected, by virtue of their positions, to engage in civic

and charitable activities." United States v. Thurston, 358 F.3d

51, 80 (1st Cir. 2004); see also United States v. Cooper, 394 F.3d

172, 176-77 (3d Cir. 2005).

The government notes our opinion in United States v. Ahlers, 4

305 F.3d 54, 60 (1st Cir. 2002), holding that a district court may

consider only a defendant's substantial assistance when imposing a

sentence below the statutory minimum pursuant to the government's

section 3553(e) motion. However, the government says it "is not

pressing this issue on appeal," because Milo would be entitled to

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if not overdone. We are not convinced that reliance on this 3

factor was overdone here.

Third, the government suggests that Milo's episode of

cocaine use in 2005 undermines the district court's finding that he

was truly contrite and would not re-offend. We agree that the

cocaine use weighs against the finding that Milo had cleaned up his

act; but the court's finding seemingly rested on Milo's overall

behavior, his charitable works, the supporting letters, and the

impression made by Milo in his elocution. The finding that Milo is

unlikely to re-offend by drug dealing is not clearly erroneous.

See United States v. Robinson, 433 F.3d 31, 38 (1st Cir. 2005).

So we are brought back to the central question of the

reasonableness of the sentence, now narrowed to focus on the two

points most stressed by the district court: contrition and

cooperation. They present quite different problems. The district

court laid the most stress on contrition, including the

unlikelihood of re-offense. We accept the finding that Milo's 4
relief from the mandatory minimum under the section 3553(f) "safety

valve," allowing the district court's consideration of Milo's

contrition in relation to the mandatory minimum. 

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contrition was real: the issue is how far this warrants a very

large reduction in sentence.

Milo received a three-level adjustment for acceptance of

responsibility. The government says that therefore the law has

already "to some extent" given him credit for contrition and that

to wipe out the rest of his sentence on this ground underscores the

unreasonableness of the sentence. But in practice over 90 percent

of drug traffickers who plead guilty get a two or three level

adjustment, whether truly contrite and unlikely to re-offend or

not. U.S. Sentencing Commission, 2005 Sourcebook of Federal

Sentencing Statistics, tbl. 19.

Real contrition, and a low chance of re-offense, can be

something more. From the standpoint of the public, re-offense is

a major concern when a defendant is sentenced for a serious crime;

and contrition is sometimes a proxy for a reduced likelihood of reoffense. The likelihood of re-offense depends on various factors

in addition to contrition; but the factors are a set of variables

regarding which, especially after Booker, the district court's

judgment deserves weight.

Yet the weight given contrition cannot be beyond review

for reasonableness. Full contrition and even a zero risk of reoffense engage major concerns of sentencing; incarceration is then
See also U.S.S.G. Ch. 1 Part A Introduction (2006) ("Most 5

observers of the criminal law agree that the ultimate aim of the

law itself, and of punishment in particular, is the control of

crime."); Pell v. Procunier, 417 U.S. 817, 822 (1974) ("An

important function of the corrections system is the deterrence of

crime."); United States v. Taylor, ___ F.3d ___, 2007 WL 2349415 at

*8 (1st Cir. Aug. 17, 2007), petition for cert. filed, No. 07-388

(U.S. Aug. 21, 2007); S. Rep. No. 98-225, at 91-92 (1983) (even if

the defendant will not re-offend, "the heightened deterrent effect

of incarceration and the readily perceivable receipt of just

punishment accorded by incarceration [are] of critical

importance").

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perhaps not needed to reform that individual, to protect the

community from him and to deter him from committing new offenses.

But punishment is also meant to deter others, affirming the

seriousness of the crime and the penalties that others will likely

face and the difficulty of avoiding punishment.

The need to deter others is under federal law a major

element in criminal sentencing, 18 U.S.C. § 3553(a)(2)(B). Given 5

that objective, we do not see how, taken alone, or combined with

the other factors described above, contrition could justify a judge

in imposing what is effectively no prison time on someone like Milo

who, without duress and simply for personal gain, operated a major

marijuana ring involving a number of individuals over an extensive

period and resulting in the distribution of thousands of pounds of

marijuana.

Many first offenders in drug distribution cases--

including young and impoverished women from other countries used to

smuggle drugs on airplanes--must be desperately sorry when caught
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and some probably could persuade judges that they would not reoffend. Yet if federally prosecuted, such individuals regularly

receive substantial jail terms. To give no significant jail

sentence on account of contrition to a major drug dealer, who has

caused far more harm with far less excuse, would rarely seem

reasonable.

Booker has added substantially to the latitude enjoyed by

district judges, but some equality or proportionality of treatment

is still an objective of sentencing and (save in very unusual

cases) extremely wide deviations from the norm can impair that

goal. See 18 U.S.C. § 3553(a)(6); United States v. Saez, 444 F.3d

15, 18 (1st Cir.), cert. denied, 127 S. Ct. 224 (2006). Further,

the lack of any real prison sentence for what is a major crime

would be very hard for the public to understand, and public

confidence in enforcement of the law is itself a value. 18 U.S.C.

§ 3553(a)(2)(A).

Sentences with no (or trivial) prison time have been

scrutinized severely on appellate review. Recently in United

States v. Taylor, ___ F.3d ___, 2007 WL 2349415 (1st Cir. Aug. 17,

2007), this court vacated a sentence of one-year of community

confinement for a defendant convicted of aiding and assisting in

the preparation of false tax returns, which carried a guidelines
Tom, 2007 WL 2822908 (disallowing six months of community 6

confinement and 36 months probation for insider trading and

obstruction of justice carrying a guidelines range of 37-46

months); United States v. Thurston, 456 F.3d 211, 215-20 (1st

Cir.), petition for cert. filed, No. 06-378 (U.S. Sep. 14, 2006)

(overturning three-month sentence for Medicare fraud carrying a

guidelines sentencing range of 63-78 months and a statutory maximum

of 60 months); Smith, 445 F.3d at 5-7 (setting aside 46-month

sentence for crack distribution carrying a guidelines sentencing

range of 100-125 months).

See also United States v. Repking, 467 F.3d 1091, 1094-96 7

(7th Cir. 2006) (vacating a one-day jail sentence and six months of

home confinement for bank defrauder who substantially assisted the

government); United States v. Saenz, 428 F.3d 1159, 1162-65 (8th

Cir. 2005) (vacating a 20-month sentence for defendant convicted of

marijuana distribution where the guidelines range was 63-78 months,

and defendant assisted the government). 

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sentencing range of 30-37 months. Other first circuit cases are to

the same effect. 

6

This circuit is hardly alone. For example, in United

States v. Wallace, 458 F.3d 606, 612-14 (7th Cir.), petition for

cert. filed, No. 06-7779 (U.S. Nov. 13, 2006), the Seventh Circuit

vacated a sentence of six months of home confinement for a

defendant convicted of wire fraud where the guidelines sentencing

range was 24-30 months, the defendant demonstrated extraordinary

remorse and lived an otherwise exemplary life, but where the

district court failed to provide an adequate justification for an

extraordinarily low sentence.7

Finally, the facts are unhelpful to Milo. He did not

commit only a single criminal act on impulse or out of desperate

need; instead, already earning a good living, he engaged in a large
See United States v. Mariano, 983 F.2d 1150, 1155 (1st Cir. 8

1993); Frank O. Bowman, III & Michael Heise, Quiet Rebellion?

Explaining Nearly a Decade of Declining Federal Drug Sentences, 86

Iowa L. Rev. 1043, 1117 (2001); John R. Steer & Paula K. Biderman,

Impact of the Federal Sentencing Guidelines on the President's

Power to Commute Sentences, 13 Fed. Sent'g Rep. 154, 155 (2000-

2001).

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number of drug transactions over a substantial period, even though

the government chose to charge them as a single conspiracy count.

In sum, the problem with contrition as justifying so low a sentence

is not the lack of explanation by the district court; it is the

result.

Milo's cooperation is an entirely different matter. One

thing that both statute and guidelines do reward is helping the

government. This is not because helping necessarily shows

contrition or other virtues (although it might be evidence) but

because, in the view of Congress and the Sentencing Commission,

assisting law enforcement is often critical to detecting and

deterring crime, and punishing offenders. In this grim calculus, 8

drug kingpins may suffer little while subordinates serve long

sentences.

Once the government moves under the guidelines or statute

based on substantial assistance, the district court is not bound by

the government's recommendation as to how much of a reduction is

proper. United States v. Martin, 455 F.3d 1227, 1235 (11th Cir.

2006); United States v. Mariano, 983 F.2d 1150, 1157 (1st Cir.

1993); U.S.S.G. § 5K1.1(a). But there are reasons for giving
-15-

weight to its recommendations and, like any other factor relied on

by a sentencing judge, the judge's own adjustment is reviewable for

reasonableness. Jimenez-Beltre, 440 F.3d at 518.

Two central realities have to be considered: first, that

the adjustment is usually a discount from the otherwise appropriate

sentence and, second, that the discount itself has costs: in

reducing protection of society from the defendant, in deterring

others, in lessening public confidence in the law's insistence on

just deserts, and in undercutting equal treatment vis-a-vis those

who similarly offended but happen to have nothing to trade.

Congress, the Sentencing Commission and most judges think

that the benefits of cooperation are worth paying a price; but

because the costs are inherent, the public interest often suggests

discounting the defendant's sentence no more than is necessary to

elicit the needed help. In any event understanding this tension

between costs and benefits helps explain why a zero jail-time

sentence for a major crime is highly suspect and also why the

prosecutor's judgment as to the right discount, if not impeached,

is worth careful attention.

Ordinarily, one facing a long prison sentence has a

strong incentive to cooperate in exchange for a reduced sentence.

How to measure cooperation is not straightforward. Partly to

assure real and not half-hearted cooperation, the government wants

to correlate the discount with results and results vary; the
See, e.g., Michael A. Simons, Retribution for Rats: 9

Cooperation, Punishment, and Atonement, 56 Vand. L. Rev. 1, 23-24

(2003) (noting risk of prosecutor's overvaluing of additional

convictions and undervaluing of general deterrence); Ian Weinstein,

Regulating the Market for Snitches, 47 Buff. L. Rev. 563, 564-65

(1999) (arguing that prosecutors and defendants do not internalize

the social costs of cooperation--such as increased sentencing

disparities).

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defendant wants compensation for the costs entailed by cooperation,

especially danger, also a variable. Still, usually needed

assistance can be elicited by some discount well short of 100

percent.

Published data on the distribution of reductions tends to

be gross, but the most recent median decrease below the guidelines

minimum in drug trafficking cases where there was a 5K1.1

substantial assistance motion was 40 months or 43.5 percent below

the guideline minimum. U.S. Sentencing Commission, 2006 Source of

Federal Sentencing Statistics, tbl. 30; see also 2005 Source of

Federal Sentencing Statistics, tbl. 30 (38.5 months or 46.2% below

the guidelines minimum). Here, the government's recommendation as

to Milo was in line with such data.

True, a prosecutor could overvalue or undervalue the

cooperation provided; the prosecutor's interest in the immediate

benefits of cooperation may suggest that the former is the greater

danger. But in general the government has both incentive and 9

expertise to recommend what is needed to secure cooperation. And

both the prosecutor and defense counsel in a district benefit from
See United States v. Desselle, 450 F.3d 179, 181 (5th Cir. 10

2006), cert. denied, 127 S. Ct. 1148 (2007) (reversing an 87-month

sentence for money laundering and cocaine distribution where

guidelines range was 262-327 months and the government 5K1.1 motion

recommended an adjusted range of 210-262 months); United States v.

Coyle, 429 F.3d 1192 (8th Cir. 2005) (reversing a 36-month sentence

for methamphetamine distribution, where guidelines range was 135-

168 months, and the government recommended a 15% reduction for

defendant's cooperation).

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a stable and predictable set of likely adjustments based on help

provided and danger entailed.

 Where minimal prison sentences have been imposed in major

drug cases based on cooperation, circuit courts have not been

reluctant to overturn them. At the very least, where a district 10

court varies widely from the government's recommendation in the

"substantial assistance" context, the district court should have

some good explanation as to why it values the defendant's

cooperation far more highly than did the government. See United

States v. Dalton, 404 F.3d 1029, 1033 (8th Cir. 2005).

In this case, Milo gave substantial help to the

government, and one can infer that some risk was involved. But the

government ordinarily insists on results to justify any assistance

reduction; results will often involve risks; and the district court

said nothing of substance here to explain why the result or the

risk in this case warranted a near-zero sentence. Indeed,

assistance was stressed less than contrition, and contrition was

not justification for so low a sentence.
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So far as based on assistance, the facially surprising

sentence in this case lacks the "plausible explanation" needed

under Jimenez-Beltre. Even taking account of both cooperation and

contrition, it is far from clear that adequate basis could be

furnished for a near-zero prison sentence. Anyway, explanation, or

the choice among sentences meaningfully above the zero level, are

in the first instance matters for the district judge on remand.

The sentence is vacated and the matter remanded to the

district court for further proceedings consistent with this

decision. If Milo is not a flight risk, the district court may let

him remain free pending re-sentencing on such terms as the district

court thinks proper.

It is so ordered.