Appeal from the United States District Court for the Northern District of Illinois, Eastern Division. No. 08 CR 741-Charles P. Kocoras, Judge.
Before EASTERBROOK, Chief Judge, and CUDAHY and POSNER, Circuit Judges. CUDAHY, Circuit Judge.
Gerald Pittman was arrested and indicted on numerous charges of distributing crack cocaine and one charge of unlawful possession of a firearm by a felon. After Pittman pleaded guilty to one of the drug charges and received a sentence that was significantly below that recommended by the Sentencing Guidelines, the government decided to prosecute Pitt-man on the remaining charges of the indictment. Pittman ended up pleading guilty to these charges as well, but argued that it would be inappropriate for the district court to increase his sentence because the government's decision to seek conviction on the remaining counts constituted vindictive prosecution. The district court rejected his argument and sentenced him to a significantly longer term of imprisonment. We affirm.
From May to August of 2008, Gerald Pittman participated in several controlled crack cocaine purchases and one controlled gun purchase with an individual who was working undercover with the police. On September 17, 2008, the police arrested Pittman. Shortly after being placed under arrest, Pittman admitted that he had been selling small amounts of crack on a daily basis for several years. He agreed to cooperate with the police and participate in a crack-related sting operation that the police were planning. On September 19, 2008, Pittman broke his deal with the police and ran from the scene of the sting operation with the $2,000 in buy money the government had provided him. The police eventually tracked Pittman down and arrested him. After being arrested, he admitted to fleeing the controlled purchase, spending the buy money and intentionally evading the police.
On February 10, 2009, a federal grand jury returned an indictment charging Pittman with six counts of distribution of crack cocaine in violation of 21 U.S.C. § 841(a)(1) and one count of unlawful possession of a firearm by a felon in violation of 18 U.S.C. § 922(g)(1). On February 17, 2009, Pittman was arraigned. He pleaded not guilty to all of the counts in the indictment.
On August 4, 2009, Pittman entered a guilty plea for one of the crack distribution counts pursuant to a written plea declaration. At the beginning of the plea colloquy, the district court sought confirmation that Pittman's plea was not entered pursuant to a plea agreement and that Pittman understood that the United States could still choose to prosecute him for the other six charges of the indictment. Pittman stated that he understood that he did not have a plea agreement with the government and that he could be tried on the remaining counts, but that he still wished to plead guilty. When pleading guilty, Pittman admitted not only to the facts underlying one of the distribution counts, but also to the facts underlying all of the other crack distribution counts. He did not admit to the facts underlying the firearm possession count.
On February 23, 2010, the district court held a sentencing hearing regarding the single charge to which Pittman had pleaded guilty. After hearing from both parties, the court sentenced Pittman to ninety-six months of imprisonment, to be followed by six years of supervised release. This sentence constituted a significant downward departure from the term of imprisonment recommended by the Sentencing Guidelines. At the close of the hearing, the government requested a status hearing concerning the remaining six counts of the indictment. The court granted the government's request and scheduled a meeting for March 3, 2010. At this status hearing, the government notified the defendant and the court that it intended to prosecute Pittman on the six outstanding counts.
On March 29, 2010, Pittman pleaded guilty to all six of the outstanding counts without a written plea agreement. On April 27, 2010, the district court held a sentencing hearing for these counts. At this hearing, Pittman argued that the government's decision to prosecute him on the charges that remained after his initial guilty plea constituted prosecutorial vindictiveness. The court rejected Pittman's argument, finding that he had been warned about what could occur prior to entering his first plea and that it was not illegal for the government to decide to proceed with prosecuting him after the first sentencing hearing. The district court sentenced Pittman to 120 months of imprisonment-the statutory minimum for the most serious charge-on all seven counts of the indictment, with all of the terms to run concurrently. Pittman seeks review of the district court's sentence in accordance with 18 U.S.C. § 3742(a), asking us to find that the government's decision to prosecute him after his initial sentencing constituted vindictive prosecution and to set aside the sentence entered by the district court at the second sentencing hearing.
Pittman's sole argument on appeal asserts that the district court committed a reversible error when it rejected his vindictive prosecution claim. When consid- ering whether a district court erred in this regard, we review the district court's factual findings for clear error and its legal conclusions de novo. United States v. Jarrett, 447 F.3d 520, 524 (7th Cir. 2006). We have juris-diction over Pittman's appeal under 28 U.S.C. § 1291.
In general, this court has considered a defendant's prosecution to be vindictive only if the defendant can show that the prosecution was pursued in retaliation for the defendant's exercise of a legal right. United States v. Cooper, 461 F.3d 850, 856 (7th Cir. 2006). A prosecution is vindictive, for example, when a defendant faces enhanced charges on retrial and the prosecutor's decision to enhance the charges is based on the prosecutor's resentment that the defendant successfully appealed his or her original conviction. United States v. Segal, 495 F.3d 826, 832-33 (7th Cir. 2007). Vindictive prosecution may also exist when it can be shown that the govern-ment's actions were motivated by the prosecutor's "personal stake in the outcome of a case" or his desire to "seek self-vindication" for prior errors that he may have committed in a case. Jarrett, 447 F.3d at 525.
We have previously noted that a "pretrial claim of vindictive prosecution is extraordinarily difficult to prove," Segal, 495 F.3d at 833, since it requires a defendant to "affirmatively show through objective evidence that the prosecutorial conduct at issue was motivated by some form of prosecutorial animus," United States v. Falcon, 347 F.3d 1000, 1004 (7th Cir. 2003). A defendant asserting a claim like Pittman's must convince the court that he would not have been prosecuted but-for the government's animus. Jarrett, 447 F.3d at 525. If a defendant is able to make this evidentiary showing, then the burden shifts to the government, which must prove that the motivation behind the prosecutorial decision was proper. United States v. Bullis, 77 F.3d 1553, 1559 (7th Cir. 1996).
Pittman argues that the district court's dismissal of his vindictive prosecution claim was improper, asserting that the timing of the government's decision to prosecute him on the additional counts and the government's statements before the district court constituted sufficient proof of animus. Pittman believes that this evidence established that the government decided to prosecute him on the remaining claims only because the district court entered a below-Guidelines sentence at the initial sentencing hearing. Pittman contends that, because the government's primary motivation in prosecuting him after his initial plea was ...