In Chapter 5, the author focuses more closely on the dynamics that existed between her grandfather, her father, and her uncle Donald. She explains that Donald began attending Fordham University in the Bronx in 1964, but he “was determined to secure a degree commensurate with his new ambitions” so he sought to transfer to the University of Pennsylvania (72). His new ambition was to replace his older brother as his father’s right-hand man at Trump Management. The author also claims that to secure his acceptance at Penn, Donald paid a friend to take his SAT for him, which she acknowledges was much easier to pull off at that time. Trump transitions to discuss her grandfather’s ambitious 1965 purchase of historic Steeplechase Park for development. Only a few months after the purchase, the project was in peril because the political connections which Fred Sr. had always relied on were no longer able to help him with the rezoning he needed (73).

While Fred Sr. continued to micromanage and disrespect Freddy at work, he did provide him with the responsibility of making Steeplechase a success, which the author suggests was done precisely because it was an impossible task.