Pleas that went wrong
These are real, reported cases. Each is a decision of the United States Supreme Court, with the person's name in the caption and the facts in the opinion. In most of them a noncitizen took a plea that nobody had read against the immigration statute first. Some of them won in the end. All of them spent years in proceedings, and one was removed before his case was decided.
Current as of October 2026. We re-check this page regularly and after any rule change.
Each case below is set out the same way: who the person was, what they pleaded to, what the immigration system then did with the plea, how the Supreme Court decided it, and what the case teaches about the plea that should have been negotiated. The teaching is the point. Almost none of these consequences turned on anything hidden. With one exception, Mr. Vartelas, they were visible in the statute the day the plea was offered.
Two men who asked, and were told not to worry
Jose Padilla
Who. A lawful permanent resident for more than forty years. He had served in the United States armed forces in Vietnam.
The plea. Transporting a large quantity of marijuana in his tractor-trailer, in Kentucky. He pleaded guilty after his lawyer told him he did not have to worry about his immigration status because he had been in the country so long.
What it did. The conviction made his removal virtually mandatory. The Kentucky Supreme Court held that the wrong advice did not matter because deportation was a collateral consequence.
The decision. The Supreme Court disagreed. Because the deportation consequence was clear from the face of the statute, counsel was required to tell him so. The duty to advise on immigration consequences has been part of the Sixth Amendment ever since.
What it teaches. Ask for the advice in writing. If the answer is "do not worry," that is the moment to get a second lawyer to read the statute.
Your right to advice before a plea →Jae Lee
Who. He came from South Korea with his parents in 1982, at thirteen, and became a lawful permanent resident. He ran two restaurants in Memphis. His parents had become citizens; he had not.
The plea. Possession of ecstasy with intent to distribute. He asked his lawyer repeatedly whether he would be deported and was assured he would not. He pleaded guilty and was sentenced to a year and a day.
What it did. The offense is an aggravated felony. Removal was mandatory, with no relief available.
The decision. The government argued he could not show prejudice because the evidence against him was overwhelming and he would have lost at trial. The Supreme Court held that a person for whom deportation is the determinative issue can rationally choose a trial with almost no chance of acquittal over a plea with a certain deportation, and that Lee had shown he would have.
What it teaches. The plea offer and the trial are not the only two choices. A plea to a different count, a different quantity, or a different statute was the third, and nobody looked for it.
Vacating a plea entered without advice →A false Social Security card, and a record that did not say which subsection
Clemente Pereida
He had lived in the United States for roughly twenty-five years, by the dissent's account, when Nebraska charged him with attempted criminal impersonation for using a fraudulent Social Security card to get a job.
He applied for cancellation of removal, which is barred by a conviction for a crime involving moral turpitude. The Nebraska statute had several subsections, at least one of which was not a crime involving moral turpitude. The record of conviction did not say which subsection he had pleaded to. The Supreme Court held that an applicant for relief carries the burden of proving the conviction is not disqualifying, and that an inconclusive record means the applicant loses.
What it teaches. The plea colloquy and the judgment are the documents the immigration judge will read. For a divisible statute, they have to name the subsection, and the subsection has to be the one that does not carry the consequence. The offense was as small as they come; the record is forever.
Four small drug cases the government called trafficking
Each of these men was a lawful permanent resident. Each pleaded to a state drug offense that most criminal lawyers would call minor. Each was charged with an aggravated felony or a controlled-substance ground, and each had to go to the Supreme Court to undo it.
Jose Antonio Lopez
A resident since 1990. In 1997 he pleaded guilty in South Dakota to aiding and abetting another person's possession of cocaine, a state felony. He was sentenced to five years and released after fifteen months, into removal proceedings on an aggravated felony charge. The Supreme Court held that a state drug offense is an illicit-trafficking aggravated felony only if it would be a felony under the federal Controlled Substances Act, and simple possession is not.
What it teaches. The state label is not the test. The federal analog is, and it has to be checked before the plea, not nine years after it.
Jose Angel Carachuri-Rosendo
In the United States since he was five, a lawful permanent resident. In 2004 he pleaded to possession of less than two ounces of marijuana, twenty days. In 2005, to possession of a single tablet of Xanax without a prescription, ten days. The government said the second conviction was an aggravated felony because it could have been charged as recidivist possession. The Supreme Court held that it was not, because the recidivist enhancement had never been charged or proved.
What it teaches. The second plea is the dangerous one. A prior on the record changes what the next plea does, which is why the tool asks for priors.
Adrian Moncrieffe
He came from Jamaica legally in 1984, at three. In 2007 a traffic stop in Georgia turned up 1.3 grams of marijuana, in the Court's words about two or three cigarettes' worth. He pleaded guilty to possession with intent to distribute and received five years' probation with judgment withheld. The government charged an illicit-trafficking aggravated felony. The Supreme Court held that a statute whose minimum conduct is sharing a small amount of marijuana for no money is not an illicit-trafficking aggravated felony.
What it teaches. Possession with intent to distribute is a distribution plea, and it put a man who arrived at three into aggravated felony proceedings for five years. A simple possession count, which was the actual conduct, would not have.
Moones Mellouli
He came from Tunisia on a student visa, earned two master's degrees, taught mathematics, became a conditional permanent resident in 2009 and a lawful permanent resident in 2011. In 2010 he was arrested in Kansas; a sock in his possession held four Adderall tablets. He pleaded guilty to a paraphernalia misdemeanor, the sock, and the record never named the drug. He was deported in 2012. In 2015 the Supreme Court held that a paraphernalia conviction that does not tie the paraphernalia to a federally scheduled substance is not a controlled-substance offense.
What it teaches. He won, three years after he was removed. The record had been negotiated well; the enforcement happened anyway, and the appeal is what saved him. Negotiate the record, and plan for the proceedings even when the record is right.
A plea at twenty, a trip to Greece, and a citizenship application
Juan Esquivel-Quintana
Admitted as a lawful permanent resident in 2000. In 2009 he pleaded no contest in California to unlawful sexual intercourse with a minor more than three years younger. The government called it sexual abuse of a minor, an aggravated felony, and he was ordered removed. The Supreme Court held that where the offense turns on age alone, the generic federal definition requires a victim under sixteen, so the conviction did not qualify.
What it teaches. The elements decide it. A plea negotiated with the federal definition on the table would have reached the same place without the removal order.
Panagis Vartelas
A Greek national, a lawful permanent resident since 1989. In 1994 he pleaded guilty to conspiracy to make or possess counterfeit securities, in his case travelers' checks. In 2003 he came home from a week visiting his parents in Greece and was treated as an applicant for admission because of the nine-year-old conviction. The Supreme Court held that the 1996 law that changed the rule for returning residents does not apply to a conviction entered before it.
What it teaches. A plea follows you to the border for the rest of your life. The travel question is part of the plea analysis, and the tool asks it.
Roselva Chaidez
A lawful permanent resident since 1977. She pleaded guilty to two counts of mail fraud for her part in a $26,000 automobile-insurance fraud, a loss over the $10,000 statutory threshold that makes fraud an aggravated felony; the conviction became final in 2004. Nothing happened until 2009, when she applied for citizenship. The application disclosed the conviction and she was placed in removal proceedings. She argued her lawyer had never advised her; the Supreme Court held that Padilla does not apply to convictions final before 2010, and she lost.
What it teaches. The record of conviction sets the loss figure, and the loss figure decides the aggravated felony. And a conviction that has been quiet for years is tested again the day you apply for anything.
Nearly all of this was visible before the plea
The aggravated felony list, the federal drug schedules, the one-year sentence, the burden of proof on relief: all of it was in the statute on the day those pleas were offered. The returning-resident rule is the exception, because Mr. Vartelas pleaded in 1994 and the law the government applied to him came in 1996. In most of these cases, what was missing was someone reading the plea against the statute.
Run the plea through the tool
Status, court, offense, sentence, priors. Every ground it triggers and everything it closes, with the rule behind each line.
Open the plea tool →For the defense lawyer
A written opinion letter or a brief on the immigration consequences, before the plea, in any state.
For criminal defense lawyers →For the defendant
A free plea review: send the charge and the offer, and we read it against the statute with you.
Request a review →Common questions
Are these real people?
Yes. Every case on this page is a published decision of the United States Supreme Court, cited by volume and page. The facts stated here are the facts stated in the opinions. We do not use composite or invented case stories on any of our sites.
Most of these people won. Why call them pleas that went wrong?
Because the plea put them in removal proceedings in the first place, and winning took years, often after a removal order and sometimes after the person had already been removed. Mr. Mellouli was deported in 2012 and won in 2015. Mr. Moncrieffe entered his plea in 2008 and won in 2013. In most of these cases, a plea read against the statute first could have avoided the proceedings, not just the final order.
What do these cases have in common?
In most of them, the conviction was treated as a category under federal law that nobody had checked before the plea: an aggravated felony, a controlled-substance offense, a crime involving moral turpitude, or a disqualifying conviction for relief. In two of them, Padilla and Lee, the defense lawyer affirmatively said there was nothing to worry about. In Pereida the record of conviction was left silent on the one fact that decided the case.
Could my plea be one of these?
Run it through the plea tool and bring the result to a lawyer. The tool applies the same rules these cases turn on: what counts as a conviction, the one-year sentence, the drug schedules, the burden of proof on relief. It does not read your statute, and the answer in your case can be different, which is why the next step is a written opinion before the plea.
Tell us about the charge before you take the plea. Not after.
You get a free conversation with an immigration attorney, in your language. We speak English, Russian, Spanish and Uzbek in-house, and we bring in a live interpreter for anything else. We will read the charge against the immigration statute, tell you what the offered plea does to your status and to every form of relief, and tell you what to ask your criminal lawyer to negotiate instead. If the plea has already been entered, we will tell you what can still be done.