In the

United States Court of Appeals

For the Seventh Circuit ____________________

No. 14-3579

RENATO DEBARTOLO,

Petitioner-Appellant,

v.

UNITED STATES OF AMERICA,

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.

____________________

ARGUED JUNE 9, 2015 — DECIDED JUNE 26, 2015

____________________

Before POSNER, KANNE, and SYKES, 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 applying for U.S. citizenship. He is married to an American citizen, 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 
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 federal 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 manufactured—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 assistance to law enforcement that DeBartolo had rendered. On 

the basis of the plea deal, the district judge sentenced DeBartolo 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 electricity theft, the state court imposed a prison sentence to run 

concurrently with his federal sentence.
No. 14-3579 3

There was no mention of deportation in the federal case. 

But unbeknownst to DeBartolo, and also it seems to his lawyer, the prosecutors, and the judge, his conviction of the 

drug offense made him deportable (“removable” is the official 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 assistance 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 removal was withdrawal of his guilty plea, which would enable him to request a trial or try to negotiate a plea of guilty to

a non-removable offense. The judge denied the petition, precipitating this appeal.

The failure to inform a defendant that if convicted he will 

be deported was held by the Supreme Court in Padilla v. Kentucky, 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 
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 different if the defendant, upon belated discovery of a deportation 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 circumstances” formula asks what he’d have done were he a reasonable person. The first standard is more congenial to the 

usual understanding of the criminal process, which is that a 
No. 14-3579 5

criminal defendant, unless mentally incompetent (in which 

event he can’t be prosecuted until cured), has a right to a jury 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 sentence now that he did then. His personal choice to roll the 

dice is enough to satisfy the “reasonable probability” standard.

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 trial, 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 circumstances. 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-
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 government says that had DeBartolo not pleaded guilty it would 

have filed an information under 21 U.S.C. § 851 noting DeBartolo’s previous drug conviction, which would have increased 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 constitutional 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, conviction 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 evidence, 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 acquitted him or convicted him of some lesser offense, such as 

simple possession of marijuana (which would not have been 
No. 14-3579 7

a basis for mandatory deportation), had the jury been given 

the option of convicting of the lesser offense. A survey conducted 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 evidence 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 favorable 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 Continues to Support Pot Legalization in U.S.,” 2014, www.gallup.

com/poll/179195/majority-continues-support-potlegalization.aspx (visited June 19, 2015).

We don’t condone jury nullification. But a criminal defendant 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 
8 No. 14-3579

reasons to reject the plea offer. He could have tried to negotiate 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 marijuana 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 children, having been born in the United States and presumably 

not knowing Italian, would not be likely to follow him to Italy.

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 imprisonment, 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 
No. 14-3579 9

the methods of enforcing them. For all one can know, if convicted in a retrial DeBartolo may not be deported when he is 

released from prison. (He will not be deported if the immigration authorities decide not to place him in removal proceedings.) His subjecting himself to a trial rather than remaining 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 matters to our decision. But it would be sensible for both DeBartolo 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.
10 No. 14-3579

The denial of the petition for relief under 28 U.S.C. § 2255

is

REVERSED.