#3 Ian Wright
Ian Wright might be a surprising addition to the list given his good reputation, but the former Gunner spent two weeks in Chelmsford prison after failing to pay a fine for driving without a license, tax or insurance. He was yet to turn professional at Arsenal and had no money to his name, but he was eventually found out and did a short sentence in the early 90s.
There was a silver lining to the incident, however, and that was Wright turning his life around from that point. The English forward vowed not to return to prison and worked hard to become an Arsenal legend. He would go on to become their all-time top goalscorer before Thierry Henry surpassed him.
Wright made over 280 appearances for Arsenal and is regarded as a legend by the supporters. By his own admission, he’s made his fair share of mistakes during his playing days, but he certainly learned from his fortnight stint in HMP Chelmsford.