Fed. R. Crim. P. 11

The State of New York indicted Santobello in 1969 on two felony counts of Promoting Gambling in the First Degree and Possession of Gambling Records in the First Degree. Santobello initially entered a plea of not guilty to both counts. After negotiations, the Assistant District Attorney agreed to permit a plea to the lesser-included offense of Possession of Gambling Records in the Second Degree and promised to make no recommendation as to sentence. On June 16, 1969, Santobello withdrew the not guilty plea and entered a guilty plea to the lesser charge. The court accepted the plea after Santobello confirmed it was voluntary and the facts described by the prosecutor were true. A series of delays followed, owing primarily to the absence of a pre-sentence report, so that by September 23, 1969, Santobello had still not been sentenced. By that date petitioner acquired new defense counsel. Petitioner's new counsel moved immediately to withdraw the guilty plea. In an accompanying affidavit, petitioner alleged that he did not know at the time of his plea that crucial evidence against him had been obtained as a result of an illegal search. In addition to his motion to withdraw his guilty plea, petitioner renewed the motion to suppress and filed a motion to inspect the grand jury minutes. These motions in turn caused further delay until November 26, 1969, when the court denied all three and set January 9, 1970, as the date for sentencing. On January 9, 1970, Santobello appeared before a different judge because the original judge had retired. A new prosecutor replaced the one who negotiated the plea and recommended the maximum one-year sentence, citing Santobello’s criminal record and alleged links with organized crime. Defense counsel objected on the ground that the State had promised no sentence recommendation and sought an adjournment to prove the promise, though the State later conceded in subsequent proceedings that the promise had been made. The sentencing judge imposed the maximum one-year sentence at the New York City Correctional Institution for men, stating that the prosecutor’s recommendation did not influence the decision. Santobello obtained a certificate of reasonable doubt and was admitted to bail pending appeal. The Appellate Division unanimously affirmed the conviction, and leave to appeal to the New York Court of Appeals was denied. Santobello then sought certiorari, which the Supreme Court granted.

Jose Padilla, a native of Honduras, has been a lawful permanent resident of the United States for more than forty years and served in the U.S. Armed Forces during the Vietnam War. He faced criminal charges in Kentucky after being arrested for transporting a large amount of marijuana in his tractor-trailer. Before entering a guilty plea to the drug distribution charges, Padilla's counsel did not advise him that the conviction would trigger deportation proceedings. Counsel instead told him that he did not have to worry about his immigration status because he had lived in the country so long. Padilla relied on that advice when he pleaded guilty and later alleged that he would have insisted on going to trial if he had received accurate information. In postconviction proceedings Padilla claimed that his attorney's erroneous advice about deportation constituted ineffective assistance. The Supreme Court of Kentucky denied relief without holding an evidentiary hearing, treating deportation as a collateral consequence outside the protection of the Sixth Amendment. The United States Supreme Court granted certiorari to review whether federal law imposed on counsel an obligation to advise Padilla that his guilty plea would result in removal from the country.

After immigration agents found 30 kilograms of marijuana in Angela Ruiz's luggage, federal prosecutors offered her what is known in the Southern District of California as a "fast track" plea bargain. That bargain—standard in that district—asks a defendant to waive indictment, trial, and an appeal. In return, the Government agrees to recommend to the sentencing judge a two-level departure downward from the otherwise applicable United States Sentencing Guidelines sentence. In Ruiz's case, a two-level departure downward would have shortened the ordinary Guidelines-specified 18-to-24-month sentencing range by 6 months, to 12-to-18 months. The prosecutors' proposed plea agreement contains a set of detailed terms. Among other things, it specifies that "any [known] information establishing the factual innocence of the defendant" "has been turned over to the defendant," and it acknowledges the Government's "continuing duty to provide such information." At the same time, it requires that the defendant "waiv[e] the right" to receive "impeachment information relating to any informants or other witnesses." The agreement also requires waiver of the right to receive information supporting any affirmative defense the defendant raises if the case goes to trial. Because Ruiz would not agree to this last-mentioned waiver, the prosecutors withdrew their bargaining offer. The Government then indicted Ruiz for unlawful drug possession. And despite the absence of any agreement, Ruiz ultimately pleaded guilty. At sentencing, Ruiz asked the judge to grant her the same two-level downward departure that the Government would have recommended had she accepted the "fast track" agreement. The Government opposed her request, and the District Court denied it, imposing a standard Guideline sentence instead. Relying on 18 U.S.C. § 3742, Ruiz appealed her sentence to the United States Court of Appeals for the Ninth Circuit. The Ninth Circuit vacated the District Court's sentencing determination. The Government sought certiorari. It stressed what it considered serious adverse practical implications of the Ninth Circuit's constitutional holding. It added that the holding is unique among courts of appeals. The Supreme Court granted the Government's petition.