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.