In a juicy new JFK Jr. tell-all, an old college buddy of John's says that the golden boy had an interesting night in 1988 with, none other than, Madonna. The book, American Legacy, claims that John and Madge met up in Chicago and checked in to a "cheap, dinky" hotel, where the duo planned on getting it on. "They were working their way around the bases, and as they rounded third and headed for home, she asked him if he had any protection. He didn't, so now they began discussing how they were going to get a hold of a prophylactic," a "good friend" of John's tells the author. "She was still legally married to Sean Penn, and he had a steady girlfriend . . . They were afraid of being busted. They couldn't very well just meander into a pharmacy and ask for a pack of Trojans. They were too well known . . . To John's great chagrin, the relationship was never completed."
The scandalous book goes on to say that John also liked men on occasion, and dipped his feet into the hooker pool every now and then. I applaud John and Madonna's will power in the situation, but I can't help but think how history might have changed if they weren't so responsible. Could Madge have been the mother of a Kennedy? Wouldn't that have been awesome?