"At the time, you just think all those things are silly," said Tommy McGorly, who used to let Milano cheat off of him in the remedial math and English classes they took together. "Most popular, most likely to succeed, whatever. It's like the tarot card nonsense. But in her case, I guess it turned out to be true."
The actress, who dabbled in soft porn when having difficulty finding roles, supported Andrew Gillum for mayor of Florida. Although Gillum actually never became mayor--he lost the race by a razor thin margin--he was found a few months later passed out on a motel room floor after a methamphetamine binge. Travis Dyson, a professional male escort, was with the married man that Milano admires.
"I'm not surprised she liked him so much," said McGorly, who graduated a year late. "She was always kinda freaky and into weird shit. I heard that, one night, she slept with the entire offensive line."
"Dude, that's not cool. Have some respect," said Gavin Wilson, who played left tackle for the 1991 state championship team.
It's not known if Milano, who has also shown support for Michael Avenatti, the "creepy porn lawyer" who went to prison for embezzling money from his clients, actually ever received the award from the high school she wasn't capable of graduating from. The school's current principal, Mr. Thompson, says it's unlikely.
"In order to win a high school award," says the administrator, "the recipient must be a student in good standing at the time he or she wins it."
That would seem to disqualify the straight D student who also failed the high school equivalency test multiple times, but Principal Thompson is willing to make an exception.
"It all depends on how bad she wants it," said the sixty-three year old who says he is often told he resembles a taller version of Danny DeVito. "I'm sure we could work something out. If you know what I mean."
At press time, Milano had earned her award.