he famously prosecuted wall street's ivan boesky, and michael mill kin. after becoming mayor of new york city in 1993, giuliani took credit for making manhattan safe again. then came 9/11. >> all that we know right now is that two airplanes struck the two large towers of the world trade center. >> reporter: giuliani was the picture of calm and strength, quickly becoming america's mayor. "time" magazine named him person of the year. >> that's the kind of leadership we need in washington. that's why i'm running for president. >> reporter: giuliani failed in his own 2008 presidential bid, but in 2016 he was back on the campaign trail, playing surrogate to donald trump. >> and he will be the leader of the change we need. >> reporter: but this was not the same rudy giuliani. he's always been aggressive and unapologetic, but now giuliani was peddling outlandish conspiracy theories. in one, he insisted that hillary clinton had some mysterious illness. >> go online and put down hillary clinton illness. take a look at the videos for yourself. >> reporter: giuliani