His acknowledgement during the 2016 presidential debates that he gamed the system by using chapter 11 bankruptcy laws to restructure his corporate debts and limit his financial obligations to his creditors without taking a significant hit to his personal liabilities. Dave Chappelle even based a skit as a satirical representation of this Trump narrative on SNL and his other shows but the broader drama that followed afterwards with characters like AG Letitia James, Eli Bartov's court testimony, judge A. Engoron's ruling and Kevin O'Leary's subsequent vocal criticism on it, from the perspective of real estate development... ruthless.