Tara Connor celebrated her 2006 Miss U.S.A. triumph by relocating to New York City and bingeing on the Big Apple's nightlife. The Kentucky native became a staple of the city's gossip pages and was soon fielding allegations of promiscuity and drug use unbecoming of her crown. Connor was summoned to pageant co-owner Donald Trump's office amid rumors that she would be stripped of her crown. The Donald surprised Connor — and himself — by sparing her his famous Apprentice catchphrase. "After speaking to her, I saw not only a beautiful woman but a beautiful heart," he said.
Connor spent a stint in a rehab facility and, after her discharge, copped to alcoholism and cocaine use. Though she swore off booze and rebuilt her life, the incident was far from over for Trump. Talk-show host Rosie O'Donnell blasted the tycoon's declaration that Connor deserved a second chance, noting that his own prior indiscretions made him an unlikely "moral compass for 20-year-olds in America." Trump shot back, dismissing Rosie as "fat" and a "real loser." And thusly a juicy feud was born.