Tired of Trump news yet? First season ‘The Apprentice’ winner Bill Rancic recently saw his one-year contract expire, the same contract he won by winning the first show. However, more than pleased with his work, Donald Trump offered a one-year extension and Rancic has accepted it. He will continue to oversee the building of Trump Tower in Chicago, while also accepting the oversight of developments in other Trump properties across the United States and Mexico. “Bill has done an incredible job in the past year working for me,” Trump says. “He’s so talented that I thought he might want to go out on his own and make millions. We’re lucky to have him back for another year.”