Renato Deb Artolo v. United States of America

In the
United States Court of Appeals
For the Seventh Circuit
____________________
No. 14-3579
R ENATO D EB ARTOLO,
Petitioner-Appellant,
v.
U NITED S TATES OF A MERICA,
Respondent-Appellee.
____________________
Appeal from the United States District Court for the
Northern District of Indiana, South Bend Division.
No. 3:14-cv-01620-RLM — Robert L. Miller, Jr., Judge.
____________________
A RGUED J UNE 9, 2015 — DECIDED J UNE 26, 2015
____________________
Before POSNER , K ANNE , and S YKES, Circuit Judges.
POSNER , Circuit Judge. Renato DeBartolo, 48 years old,
immigrated to the United States with his family at the age of
one, but unlike most of his family never got around to ap-
plying for U.S. citizenship. He is married to an American cit-
izen, however, and his seven or ten children (the correct
number is uncertain) are of course American citizens as well.
He has no family in Italy and has never learned Italian. Until

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2 No. 14-3579
recently deported to Italy, he lived in Indiana, where he
owned a small construction company from 2008 to 2010. In
1996 he had been sentenced in an Indiana court to eight
years in prison for dealing in cocaine, but the last four years
had been suspended, so he had been released after four
years; and no removal (i.e., deportation) proceedings had
been instituted against him. In 2011 he was indicted in fed-
eral court for possessing with intent to distribute more than
100 marijuana plants and with manufacturing (not the right
word—marijuana plants are grown rather than manufac-
tured—but the statutory term) more than 100 such plants
(the same plants), both being violations of 21 U.S.C.
§ 841(a)(1). He had grown the plants in a barn. Marijuana
plants need bright light to grow to their maximum size, and
DeBartolo had powered the lighting fixtures in the barn with
electricity that he stole from the electric company by running
a clandestine power line from the company’s line to his barn.
The minimum statutory prison term for the offense to
which he pleaded guilty was five years. But as a result of the
help he gave the government after his arrest to apprehend
other drug dealers in his area, and of his pleading guilty to
the manufacturing offense (thus sparing the government the
bother and uncertainty of a trial), the government moved for
a below-minimum sentence after citing the substantial assis-
tance to law enforcement that DeBartolo had rendered. On
the basis of the plea deal, the district judge sentenced DeBar-
tolo to only 25 months in prison. See 18 U.S.C. § 3553(e);
U.S.S.G. § 5K1.1. The distribution charge was dropped, and
though DeBartolo pleaded guilty in state court to the elec-
tricity theft, the state court imposed a prison sentence to run
concurrently with his federal sentence.

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No. 14-3579 3
There was no mention of deportation in the federal case.
But unbeknownst to DeBartolo, and also it seems to his law-
yer, the prosecutors, and the judge, his conviction of the
drug offense made him deportable (“removable” is the offi-
cial term) and, were he ordered removed, would prevent
him from applying for cancellation of removal. See 8 U.S.C.
§§ 1101(a)(43), 1227(a)(2)(A)(iii), (B)(i), 1229b(a)(3).
Removal proceedings were indeed instituted, and after
he completed his prison sentence he was removed to Italy,
where he remains. But while his removal case was pending
he had filed a motion in the district court under 28 U.S.C.
§ 2255(a), claiming that he had been denied effective assis-
tance of counsel in his criminal case in violation of the Sixth
Amendment, because his lawyer had failed to warn him that
if he were convicted he could well be deported; nor had he
been told by anyone else. The relief he sought in his section
2255(a) petition for the failure to warn him of the risk of re-
moval was withdrawal of his guilty plea, which would ena-
ble him to request a trial or try to negotiate a plea of guilty to
a non-removable offense. The judge denied the petition, pre-
cipitating this appeal.
The failure to inform a defendant that if convicted he will
be deported was held by the Supreme Court in Padilla v. Ken-
tucky, 559 U.S. 356, 369 (2010), to be ineffective assistance of
counsel, violative of the Sixth Amendment. As later noted in
Missouri v. Frye, 132 S. Ct. 1399, 1407 (2012), “plea bargains
have become so central to the administration of the criminal
justice system that defense counsel have responsibilities in
the plea bargain process … that must be met to render the
adequate assistance of counsel that the Sixth Amendment
requires in the criminal process at critical stages.” But there

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4 No. 14-3579
are two kickers. The defendant must show that if his counsel
had not made the error of which he complains (in this case
failing to warn the defendant that he faced deportation if
convicted, as he would be if he pleaded guilty), there was a
“reasonable probability” that he (the defendant) would have
gone to trial rather than have pleaded guilty. Hill v. Lockhart,
474 U.S. 52, 59 (1985); see also Padilla v. Kentucky, supra, 559
U.S. at 366; Kovacs v. United States, 744 F.3d 44, 51 (2d Cir.
2014). The defendant must also show that to reject the plea
bargain and go to trial would have been “rational under the
circumstances.” Padilla v. Kentucky, supra, 559 U.S. at 372;
Hernandez v. United States, 778 F.3d 1230, 1234 (11th Cir.
2015).
A mentally competent criminal defendant who decides to
stand trial even though he’s almost certain to be convicted,
and who by pleading guilty would be assured of a much
lighter sentence than if convicted after a trial, nevertheless
can’t be ordered by the judge to plead guilty; a judge can’t
plead a defendant guilty however much the plea would be
in the defendant’s best interest. Why should the rule be dif-
ferent if the defendant, upon belated discovery of a deporta-
tion threat about which his counsel failed to warn him,
chooses to withdraw a plea of guilty and risk a trial that may
result in a long sentence?
If the two verbal formulas are substantively different, the
difference is that the “reasonable probability” formula asks
only what the defendant would have done had he known he
faced deportation, while the “rational under the circum-
stances” formula asks what he’d have done were he a rea-
sonable person. The first standard is more congenial to the
usual understanding of the criminal process, which is that a

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No. 14-3579 5
criminal defendant, unless mentally incompetent (in which
event he can’t be prosecuted until cured), has a right to a ju-
ry trial no matter how slight his chances of prevailing.
DeBartolo unquestionably wants to roll the dice, which is
strong evidence that he also would have chosen to roll the
dice four years ago had he known about the deportation
threat. He faces the same risk of conviction and a long sen-
tence now that he did then. His personal choice to roll the
dice is enough to satisfy the “reasonable probability” stand-
ard.
The government wobbles between the two standards for
allowing the withdrawal of one’s guilty plea upon belated
discovery of the deportation threat. Mainly it argues—and
the district judge agreed in denying DeBartolo’s motion to
vacate his guilty plea—that the evidence is so stacked
against DeBartolo that he would not in fact have insisted on
a trial even if he’d known he’d be deported as a consequence
of pleading guilty and therefore of being convicted. But the
government also argues, though at lesser length, that it
would have been “irrational” for DeBartolo to insist on a tri-
al, which sounds like the “rational under the circumstances”
test.
Judges and prosecutors should hesitate to speculate on
what a defendant would have done in changed circumstanc-
es. The district court’s decision oversimplifies the factors that
DeBartolo would have had to weigh had he known he’d be
facing deportation if convicted, in deciding whether to seek
a trial rather than, as he did, plead guilty. The government
thought a 25-month sentence adequate punishment. How
differently would it have felt had he been tried by a jury and
convicted? Had the government sought a much heavier sen-

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6 No. 14-3579
tence in order to punish him for putting it to the bother of a
trial, mightn’t that have been deemed vindictive? The gov-
ernment says that had DeBartolo not pleaded guilty it would
have filed an information under 21 U.S.C. § 851 noting De-
Bartolo’s previous drug conviction, which would have in-
creased the mandatory minimum sentence for his current
crime from 5 to 10 years. But it does not explain why it
would have pressed for such a long sentence after having
been content with a 25-month sentence. Could a federal
prosecutor argue with a straight face that 8 years added to a
2-year sentence is a just punishment for exercising the con-
stitutional right to trial by jury in a federal criminal case?
And suppose he’d gotten a heavier sentence after the trial
just because the government and maybe the judge would
have been angry at his refusing to plead guilty. Had he been
sentenced to prison for 10 years he would be entitled to
slightly more than a year off if he behaved himself (as he
would be likely to do since he’s not a violent person and was
already 47 years old when convicted). Furthermore, convic-
tion would not have been the sure thing that the government
claims. His defense, we are told, would have been that his
marijuana project was a flop, that he had obtained only a
few ounces of the drug from it, and that he had given that
meager harvest away rather than selling it.
The government would have presented contrary evi-
dence, but in light of the growing movement to legalize the
sale of marijuana and the absence of any suggestion of guns
or violence associated with DeBartolo’s criminal activity, a
jury might have thought his offense trivial and either acquit-
ted him or convicted him of some lesser offense, such as
simple possession of marijuana (which would not have been

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No. 14-3579 7
a basis for mandatory deportation), had the jury been given
the option of convicting of the lesser offense. A survey con-
ducted in 2001 and 2002 revealed that 39 percent of potential
white jurors and 50 percent of potential black jurors would
be “very willing” or “mostly willing” to acquit, despite evi-
dence of guilt, in a first-time nonviolent drug possession
case. Lawrence D. Bobo & Victor Thompson, “Racialized
Mass Incarceration: Poverty, Prejudice, and Punishment,” in
Doing Race: 21 Essays for the 21st Century 343 (Hazel R.
Markus & Paula Moya eds., 2010) (Fig. 12.9). (Granted, this
was not the defendant’s first drug case, though a number of
years had separated the two cases.) “Montana prosecutors
were forced to offer a defendant in a marijuana case a favor-
able plea bargain after so many potential jurors said they
would nullify that the judge didn’t think he could find
enough jurors to hear the case.” Paul Butler, “Jurors Need to
Know That They Can Say No,” N.Y. Times, Dec. 20, 2011, p.
A39; see also Jesse McKinley, “Montana Jurors Raise Hopes
of Marijuana Advocates,” N.Y. Times, Dec. 23, 2010, p. A20.
Today 51 percent of adult Americans think that recreational
use of marijuana should be legal. Gallup, “Majority Contin-
ues to Support Pot Legalization in U.S.,” 2014, www.gallup.
com/poll/179195/majority-continues-support-pot-
legalization.aspx (visited June 19, 2015).
We don’t condone jury nullification. But a criminal de-
fendant cannot be denied the right to a trial, and forced to
plead guilty, because he has no sturdy legal leg to stand on
but thinks he has a chance that the jury will acquit him even
if it thinks he’s guilty.
Besides, even if DeBartolo knew that the likelihood of his
being acquitted at a trial was slim, he would still have had

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8 No. 14-3579
reasons to reject the plea offer. He could have tried to nego-
tiate a different plea deal for an offense that does not make
deportation mandatory. For example, he could have offered
to plead guilty to simple possession of 30 grams of marijua-
na and perhaps received the same 25-month sentence. Or he
might have thought a small chance of remaining with his
family in the United States worth the significant risk of a
long prison term. He might even have preferred a lengthy
prison term in the United States to a shorter prison term that
would lead more quickly to deportation, because the lengthy
prison term would at least keep him in the same country as
his family, facilitating frequent visits by family members,
which is important to prisoners. Separation from his family
may have been a big concern to him if deported, as his chil-
dren, having been born in the United States and presumably
not knowing Italian, would not be likely to follow him to Ita-
ly.
Neither the parties nor the district judge considered the
bearing of the fact that DeBartolo is seeking a trial in 2015
rather than 2011, when he pleaded guilty. Today even a 10-
year sentence would amount to only about 6 years of im-
prisonment, because he could expect not only a year or so off
the sentence for good behavior but also credit for the two
years he spent in prison and the year or so that he spent in
the custody of the immigration authorities between the end
of his prison term and his deportation.
Also to be considered is the disarray in the enforcement
of U.S. immigration law. There are believed to be at least 10
million illegal immigrants in the United States, implying
significant underenforcement of the immigration laws. There
are constant calls for reform of the laws themselves and of

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No. 14-3579 9
the methods of enforcing them. For all one can know, if con-
victed in a retrial DeBartolo may not be deported when he is
released from prison. (He will not be deported if the immi-
gration authorities decide not to place him in removal pro-
ceedings.) His subjecting himself to a trial rather than re-
maining in Italy and trying to acclimate himself to an alien
culture far from his large family is a risky venture but not an
irrational or even a reckless one. (Nor would it have been in
2011.) The probability that he will come out ahead by taking
that course may be small, but it is not trivial. He is entitled to
roll the dice.
We are mindful that the parties and the district court are
not required to consider the circumstances that DeBartolo
would face if he went to trial today. The issue required by
the Padilla line of cases to be considered is what he would
have done, at the time he had to decide whether to plead
guilty, had he known of the grave risk of being deported if
he were convicted. There was a reasonable probability that
he would not have pleaded guilty, and that is all that mat-
ters to our decision. But it would be sensible for both DeBar-
tolo and the government to consider the current situation in
assessing how to move forward. Conviction is not a forgone
conclusion, and the government should consider whether
having served the prison sentence the government originally
recommended and having then languished in the custody of
the Immigration and Naturalization Service for a year or
more and then deported to a country in which he has never
really lived, DeBartolo has been punished sufficiently and
should now be allowed to go home to his wife and children
without facing a new trial.

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10 No. 14-3579
The denial of the petition for relief under 28 U.S.C. § 2255
is
R EVERSED.

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