What happens if you win your challenge and overturn your guilty plea and then lose at trial? Can the court give you more time in prison as a penalty for successfully challenging your guilty plea? Yes, but there`s more to the story.

The Supreme Court held in North Carolina v. Pearce, 395 U.S. 711 (1969), that a longer sentence as a “penalty” upon reconviction after a successful appeal was unconstitutional. But that case was not about a successful challenge to a guilty plea. There is a difference.

In a case where a defendant did successfully challenge his guilty plea and then lost at trial and got more time, the Court distinguished its decision in Pearce, saying that loss at trial after a guilty plea is successfully overturned is not the same as a retrial. In Alabama v. Smith, 490 U.S. 794 (1989), the defendant was originally sentenced to 30 years in prison after a guilty plea. But after he overturned that guilty plea on appeal and went to trial, he lost. This time the judge said he was “too lenient” the first time and handed him 150 years in prison.

Was this unfair? The Supreme Court said it was perfectly fine, and here`s why.

The Court reasoned that a guilty plea is usually a quick court proceeding. There`s no evidence entered, usually, and the court`s duty is mainly to ensure the guilty plea is valid. That`s the whole point of a guilty plea: to ease the burden on the court and the prosecutor by the defendant admitting that he committed the crime as charged.

But in a trial all the evidence gets brought before the court. People testify, the defendant`s motives get exposed. In short, the court sees much more bad stuff about the defendant than it ever would during a guilty plea. And those facts play a part in sentencing the defendant. Judges are allowed to weigh numerous factors at sentencing, even conduct that wasn`t charged or that was part of any charges that the defendant was not found guilty of committing. Sure it seems unfair, but it`s the way it works. It`s part of the dangers of going to trial, and why so many defendants plead guilty — even if they aren`t guilty of the crimes charged.

Even if the same facts were before the court as the original sentencing but a harsher sentence was handed down the second time, it`s not considered “vindictive” if the new sentencer (a new judge or jury) imposes the harsher sentence. In United States v. Rodriguez, 602 F.3d 346 (5th Cir. 2010), it was the jury that handed out a harsher sentence after a successful challenge to a guilty and subsequent loss at trial. The court said that the jury didn`t know about the more lenient sentence given the first time around so there could not have been any vindictive motive in handing out the longer sentence the second time.

In conclusion, to answer the question of whether someone can get more time if they successfully challenge their guilty plea, the answer is a big “yes.” But maybe not if there`s another guilty plea to the same charge before the same judge. Going to trial will most likely expose someone to more time, however.