Richard Bassik, in a mug shot from the 1970s

Bassik is a Manhattan property manager of Downtown Properties who admitted to embezzling $2 million from his clients in order to support his habit. He was charged with funneling money meant for taxes, maintenance and other necessities for 13 buildings into his own secret accounts. His lawyer argued that he should be shown leniency because his thefts were the product of a "delusional belief system;" Bassik kept buying tons of tickets in the hopes of winning and being able to pay back his investors. But the Judge was not convinced by the half-hearted argument, calling it "wholly unpersuasive." He is expected to plead guilty to one count of his 25-count indictment today, and could face anywhere between 5 and 15 years in jail.

Bassik has sadly made a living performing such reckless acts. He spent 14 years in jail for kidnapping his boss's 6-year-old son on Long Island; Bassik was an insurance salesman deep in debt in 1976, and demanded $100,000 in ransom. He blindfolded the boy and held him captive for 20 hours before he was caught by police. Before that, he had been indicted in the stickup of a Long Island motel, and was on parole for a $20,000 investment scam.

Many accounts paint him as a poor business manager, and he had a bad reputation among some of his clients. "He was extremely collected, a real pro con man," said sculptor Mike Berg, who hired Bassik to manage his Hudson St. home and a commercial property on Chambers St. in 2008.