While Hill's relationship with Paul Vario may be questionable, Franzese did admit that Hill was close with Tommy DeSimone and Jimmy Burke: "He ... was part of Jimmy Burke's crew. He did know Tommy DeSimone, obviously." Burke — whose last name was changed to Conway for the film — was played by Robert De Niro, while Tommy DeSimone — last name changed to DeVito — was played by Joe Pesci, who also received an Oscar for his portrayal. Leading up to meeting Burke and DeSimone, Hill spent a lot of time mingling with mobsters, learning the rules of the mafia world. According to Biography, it's true that Hill began running errands for the mafia at a young age.
Hill's wife, Karen, really was unaware of Hill's connections when they first started dating, but would later accept it once she discovered the truth. The famous Lufthansa heist scene in the movie was also based on true events. At the time, it was the biggest heist ever pulled in America. Those involved ended up stealing $5 million, along with $850,000 in jewelry — with inflation, that would translate to $23 million today.
In the film, it's not mentioned that Hill spent time in the U.S. Army and would be discharged after starting a fight and stealing a sheriff's car. According to ESPN, Hill was the main guy behind the Boston College point shaving scandal during the 1978-79 season.