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"Jen sucks. She's difficult to work with. She's unpleasant to sit with." "I'm going to kick Kelly's butt."
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The next day in the boardroom, Kelly and Jennifer M. met with The Donald, who called the two candidates "the best of the best". Trump then gave them their last task and their ultimate test. Each candidate would oversee and manage the details of a large charity sporting event. Kelly would manage the Genworth/Trump Polo Cup to help raise money for the Alzheimer's Association while Jennifer M. would be in charge of the Genworth Charity Basketball Classic to raise money for the NBA's Read to Achieve program. Since both Kelly and Jennifer M. would be managing events for the same company, they would both be judged by the same client - a client who had a lot at stake. Since the final two were now bosses, they needed some employees. A pool of familiar faces - six fired candidates - entered the boardroom to fill the spots. Kelly chose Elizabeth, John and Raj to work for him while Jennifer picked Chris, Pamela and Stacy R. as her employees. As always, George and Carolyn would observe and report their findings.

Being a boss has its perks as Jennifer M. and Kelly discovered. Each were whisked away to their event site by a chauffeur-driven Maybach. Their employees had more modest transportation: passenger vans. Kelly and Jennifer M. didn't let their luxurious rides spoil them though; they each started planning their events during the trip. However, Kelly went a step further and had his car stop so that he could run out and hand some files to his employees so that they too could be working during the ride. In an interview, Kelly said he was aware that there was no real reward or punishment for Elizabeth, John and Raj on this task. In his own interview, Raj said he had no interest in Kelly's victory or defeat: "I'm doing this because I like winning. I couldn't give a damn about Kelly."

Kelly and his group arrived at the Greenwich Polo Club and all were impressed by the expansive and beautiful grounds. Once they settled in, the group learned about a critical task: they had to get the Genworth logo painted at the center of the polo field in a 60 foot by 60 foot area. Jennifer M.'s group arrived at Riverbank State Park where the charity basketball game would take place. Jennifer M. delegated coordinating with the NBA, the players and the emcee of the event, Sacramento King's star Chris Webber, to Pamela and Chris. Jennifer M. said that her leadership style "...is all about delegating and overseeing." But in an interview, Pamela criticized Jennifer's choices. Pamela said that she never would have handed off coordinating with the NBA if she had been the boss. She also said that a real CEO would never delegate something so important. At the polo club, Kelly's employees found a boss with a different style. John felt Kelly couldn't stop being involved in every task as Kelly meticulously tracked everything on a spreadsheet of some kind. John, Raj and Elizabeth got away from Kelly, his laptop and his spreadsheets for a bit. The trio even raced each other on the well-manicured polo field. Working in the clubhouse alone for a while, Kelly wondered where his team had gone. He worried aloud that he had three people working for him who had nothing to lose and nothing to gain while Kelly's own future hung in the balance.

As Jennifer M.'s group worked hard setting up the basketball court and preparing gift bags, she met with representatives from Genworth, who had come down for a site visit. In an interview, Jennifer M. said it was very disconcerting for the Genworth executives to arrive and see the court in its incomplete state. In her own interview, Janice Luvera of Genworth said that she was really frustrated with Jennifer M. because she felt that Jennifer M. didn't have everything worked out yet. Instead of being proactive, she felt that Jennifer M. was simply waiting for Genworth to tell her what they wanted. Janice admitted to being "nervous" and hoped that the event would not turn out to be a "disaster."

At the polo field, storm clouds were on the horizon - literally. Field painters arrived to put the Genworth logo on the grass, but the weather would not cooperate. It rained and rained hard. The painters left without even starting their task. Then, Kelly learned that Tony Bennett was coming to perform at the event. All of a sudden, the group needed a stage that they hadn't known about minutes before. Kelly said that they just had fifty things added to the other fifty they were trying to accomplish. In an interview, Kelly admitted to being "very worried" because he had no "plan B." If the polo match were canceled due to a soggy field, Kelly had no backup plan. As the rain came down, all Kelly could do was watch and hope that his dreams of becoming The Apprentice weren't being washed away with the pouring water. But Kelly's event wasn't the only one threatened with disaster. Jennifer M. was on the phone with Chris Webber's assistant and learned that the basketball star slated to headline the event was canceling. In an interview, Jennifer said, "I'm not letting Chris Webber go without a fight." But she also said that losing Chris Webber as the emcee, "...basically blows the entire event."

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