John Thomas fill serve five years in prison after being convicted of scamming the city of Riverdale in Chicago out of $370,000, and the man who once considered himself invincible sobbed uncontrollably in court when faced with his actions.

Thomas claimed to have used drugs, guzzled wine and vodka, and had bedded more than 2,000 women, but in the end he was wearing wires for the feds to put some powerful political figures in prison in order to get a reduced sentence, according to a Chicago Sun-Times report.

Chicago is a city known for its corruption, and Thomas helped Riverdale fit that profile by stealing more than $370,000 in tax increment financing money from the suburban city on the south side. He sobbed in court and said he had “total and utter remorse and embarrassment” over stealing the money, saying that he was broken up about his separation from his wife and his 8-year-old daughter.

He defended himself in court as someone who was not the “hurtful con man” that others have made him to be, according to the report. He was shackled and wearing an orange jumpsuit in court.

U.S. District Judge James Zagel acknowledged that Thomas probably cared for his family, but other than that he didn’t think he cared about anything at all.

In the end, Zagel would actually increase the sentence for Thomas beyond what prosecutors had asked for, giving him five years in prison instead of the 57 months that had been recommended.

Thomas didn’t have much going for him in the eyes of the court in terms of leniency, as in the 1990s he had been convicted in a billboard scam in New York, meaning that he had blown his second chance.