Four People Who Won Elections From Jail

You’d think one of the surest-fire disqualifications for someone running to pass, execute, or interpret the law would be to demonstrably break it, but sometimes, not even that puts a damper on voters’ spirits.

We may very well have a president elected from prison soon, so let’s try to learn from our history. Here are four politicians who won elections from prison…

4 Andrew Wilhoite

In May 2022, Wilhoite won the Republican primary for a seat on the Clinton township board in Indiana. Unfortunately, he had to withdraw from the general election, seeing as two months earlier, he’d admitted to police that he’d knocked his wife unconscious with a flowerpot and then dumped her body from a bridge into a nearby creek, where she was later found dead. In 2024, he was convicted of voluntary manslaughter and faces up to 30 years in prison, so that probably puts an end to his political career. Probably.

3 Joseph Morrissey

In 2014, Morrissey resigned from the Virginia State Senate. He was about to plead guilty to charges related to a sexual relationship with his 17-year-old secretary, so he sort of had to — voters tend to frown on that kind of thing. Except these ones, because he immediately changed his mind and won the special election triggered by his own resignation, while serving a six-month sentence. He was later charged with election law violations for essentially being nice to poll workers and was never elected again, because that’s apparently where Virginia draws the line.

2 Greg Gianforte

As a politician, the time to body slam a reporter is never, but it’s definitely not the night before election day. You might think that Montana voters simply hadn’t had enough time to find out that Gianforte had been charged with doing just that before they voted him into office as their new congressman in 2017, but journalists on the scene reported that they “hadn’t found anyone … who changed their mind.” Technically, Gianforte wasn’t in jail during the election, but the incident cemented his position as a Trump toady, which is its own kind of prison.

1 Joel Caston

In 2021, Caston was elected advisory neighborhood commissioner of a section of Washington, D.C., but the fact that he had been in prison for more than 20 years at the time is only one of the weird parts of the story. His only opponents were other inmates, as the seat had long been vacant and forgotten about, so he was kind of a shoo-in, and the area he ended up overseeing included the very prison where he was serving his sentence. He’d actually already been granted parole by the time he won, and in 2024, he was appointed to the D.C. Sentencing Commission, which advises the city on sentencing guidelines.

Just a little feel-good story before our long national nightmare begins.