United States of America v. Jose Luis Diaz-Jimenez

In the
United States Court of Appeals
For the Seventh Circuit
No. 10-1988
UNITED STATES OF AMERICA,
Plaintiff-Appellee,
v.
JOSE LUIS DIAZ-JIMENEZ,
Defendant-Appellant.
Appeal from the United States District Court
for the Eastern District of Wisconsin.
No. 09-CR-262—Rudolph T. Randa, Judge.
ARGUED AUGUST 4, 2010—DECIDED SEPTEMBER 8, 2010
Before POSNER, ROVNER, and HAMILTON, Circuit Judges.
POSNER, Circuit Judge. The defendant, a Mexican citi-
zen, pleaded guilty to having been present in the
United States illegally because he had been removed as
a consequence of having been convicted of an ag-
gravated felony (car theft). 8 U.S.C. §§ 1326(a), (b)(2).
He had re-entered the United States on four previous
occasions after his conviction but on each occasion had
been sent back to Mexico without being prosecuted.

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2 No. 10-1988
In exchange for his pleading guilty to the immigration
offense, the government agreed to recommend a sen-
tence at the bottom of the guidelines range, which was
18 to 24 months. But at the sentencing hearing the pros-
ecutor, mistakenly though apparently in good faith,
initially recommended that the defendant be sentenced
at the top of the range. (The prosecutor may have failed
to review the plea agreement before the hearing.) He
emphasized the defendant’s repeated illegal entries
into the United States after being removed. “So a signifi-
cant penalty has to be applied so . . . it is more aversive
for him to come back to more time in prison, than it is
for him to just try his luck again. Our recommendation,
Judge, is the Court impose 24 months, the high end of
the guideline range.”
Defense counsel immediately objected on the basis of
the government’s promise in the plea agreement. The
prosecutor responded by saying “I see that, Judge. It’s my
fault . . . . I got the morning wrong, and the afternoon
wrong” (he had said to the judge at the beginning of
the sentencing hearing “Good afternoon again, Your
Honor,” when actually it was morning) “and my recom-
mendation wrong. I think, Judge, the point is that a
significant sentence needs to be meted out so that it
is aversive enough to keep the Defendant from coming
back. The reality of whether it’s 18 months or greater,
that is still a significant period of time. And we’d ask
the Court to impose that low end of the guideline range,
no greater than is necessary to achieve the result.
I suppose a larger sentence could be appropriate, but

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No. 10-1988 3
that is the least amount that is necessary to achieve the
desired result. And for that reason, it’s appropriate
under [18 U.S.C. §] 3553[a].” Defense counsel responded:
“I guess after that kind of mixed recommendation for a
low end, I would state that I believe a low end would
be appropriate in this case.” He explained that the de-
fendant was young and had gotten into trouble by
taking illegal drugs but was not a dealer.
Without mentioning the government’s recommenda-
tion in the plea agreement, or the prosecutor’s mistake
and retraction, the judge sentenced the defendant to
21 months in prison. The judge would have given him
24 months, he said, had he not wanted to save the tax-
payer the estimated $6,000 cost of imprisoning the de-
fendant for another three months.
The defendant argues that the government violated
the plea agreement and that he should be resentenced
by a different judge. There is an initial question whether
defense counsel failed to challenge the violation in
the district court, and thus committed a forfeiture that
would limit the scope of our appellate review to cor-
rection of a “plain error” by the district court. We think
not. He did object, and having done so explained why
he thought his client should be sentenced at the bottom
of the guidelines range, as the government had promised
to recommend. He remarked that the government’s
recommendation was “mixed,” and that is an apt charac-
terization, as we’ll see.
A plea agreement is a form of contract. A breach is
actionable, and a minimum remedy is specific perform-

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4 No. 10-1988
ance and resentencing by a different judge. Santobello v.
New York, 404 U.S. 257, 263 (1971); United States v. Grimm,
170 F.3d 760, 765 (7th Cir. 1999); United States v. Griffin,
510 F.3d 354, 367 (2d Cir. 2007). Maximum is allowing
the defendant to withdraw his plea; the Court in
Santobello left it to the lower court “to decide whether
the circumstances of this case require only that there be
specific performance of the agreement on the plea, in
which case petitioner should be resentenced by a dif-
ferent judge, or whether, in the view of the [lower] court,
the circumstances require granting the relief sought by
petitioner, i.e., the opportunity to withdraw his plea of
guilty.” 404 U.S. at 263.
The second alternative, rescission of the plea agree-
ment, is not adequate if the defendant doesn’t want to
withdraw his plea and gamble on negotiating a better
agreement; and our defendant doesn’t want to do that.
So the only question is whether the breach was mate-
rial. In contract law, although a breach is a breach, if it
causes no harm then all that the other party is entitled to
by way of remedy is nominal damages, which means, as
a practical matter, no relief. Habitat Education Center
v. U.S. Forest Service, 607 F.3d 453, 460-61 (7th Cir. 2010).
The cases reach the same result when the breach of a
plea agreement is, in the court’s view, insubstantial,
immaterial, technical—in short, minor—or cured on the
spot and in either case undeserving of substantial relief
such as resentencing or withdrawal of a guilty plea. E.g.,
Hartjes v. Endicott, 456 F.3d 786, 790 (7th Cir. 2006); United
States v. Amico, 416 F.3d 163, 165-68 and n. 3 (2d Cir. 2005).

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No. 10-1988 5
The government’s recommendation for lenity is an
important part of the consideration for a defendant’s
entering a plea of guilty (though often the most
important part is the guidelines sentencing discount for
acceptance of responsibility, which ordinarily requires
such a plea). But most courts, including our own, have
not taken the extreme position that any violation of a
promise to recommend a lighter sentence than might
be expected automatically requires reversal—that it can
never be deemed minor or curable. United States v.
Salazar, 453 F.3d 911, 915 (7th Cir. 2006). Even cases that
lean toward a rule of automatic reversal (and they are
the minority) recognize exceptions. See, e.g., United States
v. E.V., 500 F.3d 747, 754-55 and n. 13 (8th Cir. 2007);
United States v. Mosley, 505 F.3d 804, 810 n. 1 (8th Cir.
2007). Although United States v. Kurkculer, 918 F.2d 295,
302 (1st Cir. 1990), does not, a later decision by the
same court does. United States v. Clark, 55 F.3d 9, 13 n. 3
(1st Cir. 1995).
Oddly, the cases conjoin recognition of exceptions
with rejection of the application of the doctrine of
harmless error, e.g., United States v. Mosley, supra, 505
F.3d at 810; United States v. VanDam, 493 F.3d 1194, 1202-
03 (10th Cir. 2007); cf. Dunn v. Colleran, 247 F.3d 450,
461 (3d Cir. 2001); United States v. Mondragon, 228 F.3d
978, 981 (9th Cir. 2000); but see United States v. Belt, 89
F.3d 710, 713 (10th Cir. 1996), and try to square the circle
by remarking, for example, that Santobello “rejected the
argument that the breach of the plea agreement was
harmless” but “does not amplify the parameters of what
constitutes a breach.” Smith v. Stegall, 385 F.3d 993, 999

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6 No. 10-1988
(6th Cir. 2004). We can’t see the difference between
calling a breach of the plea agreement a harmless error
and calling it immaterial. Anyway the Supreme Court in
Santobello didn’t say that the doctrine of harmless error
is inapplicable to breach of a plea agreement; it said
that the fact that the prosecutor’s error was inadvertent
did not excuse the breach, that the judge’s saying he
hadn’t been influenced by the prosecutor’s error was
also not a cure, and that the defendant was entitled to
enforcement of the government’s promise in the plea
agreement. None of that amounts to saying that the
defendant would be entitled to enforcement even if,
were the agreement a civil contract, he would not be
because the breach was inconsequential.
The Court later declared it an open question
“whether Santobello’s automatic-reversal rule has sur-
vived our recent elaboration of harmless-error principles
in such cases as [Arizona v.] Fulminante[, 499 U.S. 279,
310 (1991)] and Neder [v. United States, 527 U.S. 1, 9
(1999)].” Puckett v. United States, 129 S. Ct. 1423, 1432 n. 3
(2009). This makes it sound as if Santobello had rejected
the application of the doctrine of harmless error to
breaches of plea agreements. But this interpretation is
undermined by the Court’s discussion in the text of
Puckett to which the footnote from which we just quoted
is appended. The doctrine of harmless error is gen-
erally held inapplicable only to fundamental procedural
errors (confusingly called “structural” errors), such as
refusing to allow a criminal defendant to be represented
by a lawyer. United States v. Gonzalez-Lopez, 548 U.S. 140,
149-50 (2006); Ashford v. Gilmore, 167 F.3d 1130, 1136 (7th

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No. 10-1988 7
Cir. 1999). The Court in Puckett said that “breach of a plea
deal is not a ‘structural’ error as we have used that term.
We have never described it as such, and it shares
no common features with errors we have held structural.
A plea breach does not ‘necessarily render a criminal
trial fundamentally unfair or an unreliable vehicle for
determining guilt or innocence’; it does not ‘defy analysis
by “harmless-error” standards’ by affecting the entire
adjudicatory framework and the ‘difficulty of assessing
the effect of the error’ is no greater with respect to plea
breaches at sentencing than with respect to other pro-
cedural errors at sentencing, which are routinely subject
to harmlessness review. Santobello did hold that auto-
matic reversal is warranted when an objection to the
Government’s breach of a plea agreement has been pre-
served, but that holding rested not upon the premise
that plea-breach errors are (like ‘structural’ errors) some-
how not susceptible, or not amenable, to review for harm-
lessness, but rather upon a policy interest in establishing
the trust between defendants and prosecutors that is
necessary to sustain plea bargaining—an ‘essential’ and
‘highly desirable’ part of the criminal process.” 129 S. Ct.
at 1432 (citations omitted; emphases in original). In
neither Santobello nor Puckett did the Court say that the
maintenance of this trust excludes a concept of
immaterial breach.
It’s true, as the defendant’s lawyer reminds us, that a
bell cannot be unrung. But a mistake is not a bell, and
usually can be corrected. While Santobello and the cases
following it do not allow the judge to dissolve the error

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8 No. 10-1988
by stating that he won’t be influenced by it, Santobello v.
New York, supra, 404 U.S. at 262-63; United States v.
Williams, 102 F.3d 923, 926 n. 5 (7th Cir. 1996); United
States v. Griffin, 510 F.3d 354, 366 (2d Cir. 2007), as that
is too facile a cure, subsequent actions by the prosecu-
tion can justify an inference that the error was indeed
harmless. United States v. Amico, supra, 416 F.3d at 165;
United States v. Brody, 808 F.2d 944, 948 (2d Cir. 1986).
Suppose the prosecutor in this case had said, after his
mistake was pointed out, “I misremembered the plea
agreement. I agree unreservedly with the recommenda-
tion in the plea agreement for an 18-month sentence.
That sentence would in our opinion be sufficient; we
do not think there is any need for a longer sentence.” Such
a corrective statement would be analogous to a contract
party’s curing his breach before it did any harm to the
other party. See, e.g., UCC § 2-508(1); Bodine Sewer, Inc.
v. Eastern Illinois Precast, Inc., 493 N.E.2d 705, 711-12 (Ill.
App. 1986).
We are not suggesting “safe harbor” language, or that a
properly abject apology and retraction are a sure cure
for any misrepresentation of the terms of a plea agree-
ment. The prosecutor might have indicated by his
remarks before the mistake was discovered his strong
commitment to a sentence at the high end of the guide-
lines. He didn’t quite do that in this case. But neither
did he make the kind of unequivocal retraction that we
illustrated in the preceding paragraph. He began his
acknowledgment of error by equivocating over whether
an adequately “aversive” sentence, in light of the de-
fendant’s yo-yoing across the U.S.-Mexican border, was

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No. 10-1988 9
18 months (the recommendation in the plea agreement)
or “greater.” This equivocation undermined his endorse-
ment of the recommendation in the plea agreement. In
emphasizing the need for a sentence that would dis-
courage the defendant from again returning to the
United States, he was making a point that the judge in
sentencing the defendant to 21 months called “a great
point.”
The prosecutor further undermined the plea agree-
ment by saying “I suppose a larger sentence could be
appropriate, but that [i.e., an 18-month sentence] is the
least amount that is necessary to achieve the desired
result.” If 18 months is the least amount of prison time
necessary to deter the defendant from returning
illegally to the United States, and a longer sentence
might therefore be appropriate, this is recommending
to the judge, inconsistently with the plea agreement, that
he sentence the defendant to at least 18 months, and
more if the judge wants, since a longer sentence could
be “appropriate” too.
So there was a serious breach of the plea agreement,
and so the defendant is entitled to be resentenced
by a different judge. Of course the new judge will have
read this opinion before sentencing the defendant. But
that doesn’t mean the judge will be influenced by
the “mixed” recommendation. We expect that a different
prosecutor from the U.S. Attorney’s office will appear
before that judge, apologize for the clumsy mistake of
the previous prosecutor, and recommend an 18-month
sentence without any ifs, ands, or buts. That will pro-

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10 No. 10-1988
vide the defendant with adequate relief—indeed as
much relief as he is asking for in this appeal.
REVERSED AND REMANDED,
WITH DIRECTIONS.
9-8-10

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