A Man Sues the Widow of the Man He Murdered for Not Letting Him Go to His Preferred Jail

Shandola was friends with Robert Henry, and the two decided to start a joint business venture together. In 1995, said venture sadly failed, and Shandola reacted in the most mature manner he knew how: by shooting Henry to death with a shotgun

Shandola was sentenced to 31 years in prison, so Henry's family figured that would be the end of their nightmare. But 18 years after murdering Henry, Shandola decided the time was right to sue Henry's family
Shandola sued Henry's widow, Paula, and three others for $ 1000,000 a piece

His reasoning made every last bit of sense in the world -- he wanted to transfer to a Canadian prison, since that's where he's from.
Henry's widow, Paula, had written a letter to the court asking that his request be denied
In Shandola's lawsuit, he claimed that Paula Henry invaded his privacy and intentionally caused emotional distress by not allowing him to serve his sentence in his home country.

The judge, as judges are wont to do in these situations, dismissed the case. However, he didn't just dismiss it; he ordered Shandola to pay Paula Henry, and the three others, $10,000 a piece, or $40,000 total. That might seem like an awful lot to ask of a guy who hasn't had a job in close to 20 years, but in cases like this, it's the thought that counts.