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Perdew emerged victorious after a high-pressure final challenge in which Perdew, 37, was charged with organizing a charity polo match (complete with a performance by Tony Bennett), while Massey, 30, was placed in charge of a charity basketball game and silent auction.
Trump told Perdew: "Kelly you had a very good record. I'm not so sure you can take that great military background and put it into business. Jennifer, nevertheless, I have to say, you're fired.
"Kelly, you're hired," Trump said.
"It's phenomenal," Perdew said in his final limo ride away from New York's Lincoln Center, where Trump announced his decision before a live audience. Joining in the post-party were cohost Regis Philbin and Apprentice contestants from both seasons.
For Jennifer, the San Francisco-based attorney, her charity basketball game encountered trouble from the start, when the event's proposed emcee, the Sacramento Kings' Chris Webber, bowed out hours before the game was set to begin.
At the Greenwich Polo Club in Connecticut, the situation wasn't much better. Rain threatened to halt Perdew's polo match, as his staff – comprised of three previously fired Apprentices: Raj, John and Elizabeth – threatened mutiny.
The situation did not look good for either candidate. Jen's teammates, Pamela, Stacy R. and Chris, complained that Jen was delegating too many of her duties, and a representative from Xbox, one of the event sponsors, came unplugged when the power to the televisions and Xboxes shut down. At the same time, executives from event's main sponsor, Genworth Financial, doubted her ability to pull the game together.
On the polo field, Elizabeth chewed out Raj and John, who she believed were not working hard enough. Kelly was forced to intervene and make the team work together. It was one crisis after another, as a logo from one of his event's sponsors that was supposed to be painted on the field had to be moved, because it might scare the horses.
Over at the basketball game, Trump was left confused when Jen greeted him, and then quickly disappeared for the remainder of the game to help set up the post-party. Afterward, as Trump called the disappearing act "a little strange."
"In many ways they did a great job, but in other ways it was lacking," Trump said.
Meanwhile, back in Greenwich, the match ultimately went off without a hitch, complete with the performance by Bennett.
In the end, Perdew and Massey were forced to face Trump and plead their case in a live boardroom showdown at Lincoln Center. After getting endorsements from his real-life colleagues and from original Apprentice winner Bill Rancic, Perdew played up his winning record throughout the season. Massey, whose teams lost more often than won, played up her school credentials, graduating at the top of her class at Princeton and Harvard.
JOSH & FERGIE: ROCKED BY SCANDAL
Did he cheat with a stripper?
Married less than a year, the couple denies an Atlanta woman’s claims that she and Josh had a fling
Note that this week’s cover of PEOPLE may differ regionally
