trump liked how he dealt with hecklers and hired him as a security guard, calimari climbed the ranks and eventually chief operating officer. i got some of the best people in the world. i have guys lined up. believe me. reporter: in his role overseeing trump security team, calimari has come under scrutiny for allowing blacks policy and using force, particularly when trump was using him during the 2016 feign i campaign. the third official left his gig in 2007 at the new york city department of parks and recreation. now, lieberman works closely with weiselberg on financial matters, a source tells cnn. since joining the company, he s helped rank high profiles in the city. a sweet deal for trump that caught the eye of at least one law maker this week.