Being a professional con-man is not without it's risks. Either their massive ego causes them to become so delusional in thinking they're invincible that they slip up and land in jail. Or the incredible stress of having to constantly find new ways to keep the scam afloat causes a stroke, heart attack or something similar. Both things happened to Eddie's mentors at IGI. One (age 70) is rotting in prison for 17 years and the other just dropped dead in his mid 50's.