Celebrity Apprentice winner is tall, ponytailed entertainer. Trace Adkins, the gruff country star who returned to "All-Star Celebrity Apprentice" holding his nose, squeaked out a win against magician Penn Jillette, a creative whiz who had more wins to his name but didn't raise as much money in the final task. Trace won $250,000 (plus his earlier winnings) for the American Red Cross, which aided his family when their house burned down in 2011. Penn did add to his earlier winnings as well, with $100,000 for his charity, Opportunity Village, from Walgreens for developing the better selling ice cream in the last challenge, which tasked them with creating a unique ice cream flavor, packaging it, creating a 60-second promotional video and selling up to 50 tickets to a VIP event they must organize. Trump judged the pair on flavor, brand messaging and creativity of both the video and project packaging, overall presentation and additional money raised through ticket sales.