In 1988, Wisconsin man makes $800 in fraudulent credit card charges. He spends the next 25 years on probation or imprisoned for probation violations. Yikes! Turns out his sentence legally ended in 1995. Seventh Circuit: The man can absolutely sue about that. Because he couldn’t sue for damages while he was under supervision, his claims are timely now. And a jury could find that some of the defendants were deliberately indifferent to his illegal sentence.