simon has a checkered an unusual history. this year he pled guilty to tax fraud. >> all the charges are unrelated to michael cohen, but the company he keeps is noticeable. >> after running for new york city counsel in 2003 and losing in a landslide, cohen turned his attention to real estate. he used his earliest deals to attract the attention of a man whose brash persona and glamorous lifestyle made him a reality tv star. >> you're fired. >> donald j. trump was enjoying fame on his hit show, "the apprentice." >> trump building and later a $5 million property in another building, where ivanka trump lived. >> after becoming treasurer of trump world tower, he proved value to donald trump for the first time. >> donald trump is impressed by the effort that michael cohen helped lead to pose a tennis movement in the trump building to reorganize the building. >> he took trump's side against the others in the building, and trump was grateful. >> cohen's ambition was rewarded in 2006 when he became a lawyer for donald trump and shortly after, executive vice president of the trump organization. michael cohen had found it. >> it was alluring