In 2005, a 34-year old Pinkett along with 17 other contestants entered the fourth series of The Apprentice. His wife downloaded the application form, planting the idea of auditioning for the show in his mind. The Apprentice is a reality television series which premiered in January 2004, in which American entrepreneur Donald Trump uses a series of tasks and a process of elimination to ultimately select one candidate for a yearlong apprenticeship with one of his companies. The fourth season began filming in May 2005 and began airing September 2005, with the finale airing in two-parts on the Thursday night of December 8 and 15, 2005. Pinkett reached the finale with one other contestant, 23 year old financial journalist Rebecca Jarvis. Pinkett was to organise a celebrity ball-game for Autism Speaks, while Jarvis' task was to stage a comedy night in aid of the Elizabeth Glaser Pediatric AIDS Foundation. Despite the game being rained out, Pinkett raised nearly $11,000.
In the final judgement, Pinkett was criticised by Trump for not spotlighting the celebrities in attendance at his event, and by Trump's advisor Carolyn Kepcher for not having a backup plan when the weather turned. Despite this, Pinkett was chosen by Trump as the winner, describing Pinkett as an "amazing leader" and saying "Rarely have I seen a leader as good as you, and you lead through niceness". Moments after the announcement, Trump asked Pinkett his opinion as to whether he should take the unprecedented step and also hire the "outstanding" Jarvis too. In his reply, Pinkett asserted that there could only be one winner of the contest, a view which Trump chose to agree with. This stance attracted much comment after the show, with Pinkett later defending his rationale, but making it clear he had no objection to Jarvis being hired by the Trump organization at a later date. The reactions had taken Pinkett by surprise, but he later stated he remained on good terms with Jarvis.
Pinkett started his apprenticeship on February 6, 2006. His task was to oversee the $110m renovation of the Taj Mahal, the Plaza and the Marina, three casino resorts operated by Trump Entertainment Resorts in Atlantic City, New Jersey.
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