Season 5 |
| 66 :05x01 - Summer of Sam's (Feb/27/2006) | | Eighteen candidates journey to Republic Airport in New York to meet Donald Trump on his plane and begin their 15-week job interview. For their first task, the teams utilize enormous blimps to market the billion-dollar, members-only warehouse business. | |
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| 67 :05x02 - The Razor's Edge (Mar/06/2006) | | The candidates' second task involves a marketing campaign that challenges New Yorkers to text message on their mobile phones. One team's project manager learns a lesson in leadership while the other has a difficult time dealing with an awkward acting teammate. The winners are treated to a charitable reward while the losers face the boardroom. | |
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| 68 :05x03 - Get it in Gear (Mar/13/2006) | | The candidates throw a corporate retreat for car dealership owners of the world's largest automaker. While one team focuses on an outdoor experience, the other team looks at throwing a classy event. The winners swim with the ocean's deadliest predators while the losers head to the boardroom where the fourth candidate is sent home. | |
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| 69 :05x04 - Cereal Killers (Mar/20/2006) | | The would-be magnates design billboards to launch a new product for a monster cereal company. One project manager attempts to unite their team amid adversity while the other team struggles with an annoying teammate. The winners break bread with a world-famous chef while the losers get chewed out in the boardroom, and another candidate is fired. | |
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| 70 :05x05 - Cruise Control (Mar/27/2006) | | The candidates race against the clock to shoot a commercial aboard a cruise ship that's set to sail. One project manager clashes with a mutinous teammate while the other project manager alienates everybody. The winners are rewarded with a bounty of treasure, while the losers head to the boardroom where another candidate is sent home. | |
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| 71 :05x06 - King of the Jingle (Apr/03/2006) | | The would-be tycoons take on the world of music when they write an advertising jingle for a major restaurant chain. One team finds their groove right away while the other contends with an out-of-tune teammate. The winners enjoy a scrumptious reward and the losers face the music in the boardroom. | |
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| 72 :05x07 - It's More Than D'Cor (Apr/10/2006) | | The candidates battle it out in the billion-dollar renovation business creating themed activity areas for a national children's charity. One project manager nails the concept but drives everyone crazy because they can't make a decision. The other team watches as their project manager butts heads with a negative teammate. The winners help make a child's dream come true, while the losers face a hammering in the boardroom by The Donald. | |
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| 73 :05x08 - A Slice Of Heaven (Apr/10/2006) | | The ten remaining candidates launch a new pizza sandwich for a major convenience retailer. One candidate volunteers to switch sides to help out a losing team. Another candidate attempts to make the biggest sale imaginable. The winners jet out of town to dine with a U.S. Senator while the losers get grilled in the boardroom. | | Guest Stars: Charles Schumer as Himself | |
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| 74 :05x09 - Assault on Battery (Apr/24/2006) | | Donald Trump's children Ivanka and Donald Jr. watch as the candidates engage in an all-out street war while promoting one of New York City's biggest tourist attractions. One team goes for broke in an effort to end a horrible losing streak, while the other struggles with an insubordinate teammate. The winners hit the links with one of the world's best golfers, while the losers head to the boardroom where another candidate is fired. | |
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| 75 :05x10 - Blow Out (May/01/2006) | | The eight remaining candidates travel to Long Island to put together grand openings for two new hair salons. One project manager decides to get his hair done while a romance may or not be blossoming on the other team. The winners collaborate with a legendary songwriter, while the losers sing a different tune in a particularly heated boardroom. | |
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| 76 :05x11 - Back to School (May/08/2006) | | The candidates relive their younger days by putting on a tailgate party during a college football game. One team creates a spectacle with an eating contest while members of the other team dress up as cheerleaders. The winners wine and dine in the country, while the losers face a fierce boardroom. | |
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| 77 :05x12 - Backs against the Wal-Mart (May/15/2006) | | The final five are challenged to create an in-store display for a videogame console in one of the biggest retail chains in the country. One candidate feels they are being undermined by their team, while the other group worries that their display will not be completed in time. The winners take a private jet to Hollywood and get a chance to appear in a movie, while the losers face off in the boardroom. | |
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| 78 :05x13 - Who Wears The Pants (May/22/2006) | | The final four candidates create a new line of uniforms for the nation's largest brand of upscale, all-suite hotels. One team uses its love of fashion to try to stitch together a win, while the other team models its designs on market research. The winners hit the town with Trump's favorite apprentices, while the losers struggle to survive the boardroom. | |
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| 79 :05x14 - The Final Battle (May/29/2006) | | The final two candidates take on their toughest tasks yet, coordinating two massive charity events. One finalist faces off with a tough executive while putting on a celebrity hockey event and the other lets his heart lead him astray while staging a massive rock concert in Atlantic City. | |
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| 80 :05x15 - Season Finale (Jun/05/2006) | | The finalists scramble to complete their most difficult tasks to date, then go head to head in the final boardroom. The winner is announced live from Los Angeles. | | Guest Stars: Randal Pinkett as Himself | |
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