On June 14, 1986, Trump's 40th birthday, he explains that Roy Cohn died of AIDS. Cohn died on August 2, 1986.
In a scene set in the 1980s, Trump offers a boy a piece of Trump Steak, which hit the market in 2007.
The video was supposedly made in 1988, but the aspect ratio is 16:9, which wasn't used in American broadcast TV until the late 1990s.
At the bar, Trump refers to Roy Cohn as "right-hand man to Senator Eugene McCarthy." Cohn worked for anti-Communist Republican Senator Joseph McCarthy, not Liberal Democratic Minnesota Senator Eugene McCarthy.