Trump: The Game is a board game depicting Donald Trump. Milton Bradley Company initially released the game in 1989, but it sold only 800,000 copies out of an expected two million. Parker Brothers re-released Trump: The Game in 2004 following the success of Trump's reality television series, The Apprentice, from earlier that year. Trump: The Game received mixed reviews from critics.

Jeffrey Breslow pitched the game to Donald Trump in his office at Trump Tower in New York. As Breslow explained the concept, Trump interrupted to say, "I like it—what's next?" Trump received offers from four toy companies that were interested in releasing the game. Trump chose Milton Bradley Company, which he called "the Rolls-Royce of game companies." Parker Brothers declined an offer to produce the game. After receiving approval from Trump, Breslow sold the concept for the game to Milton Bradley and then held another meeting with Trump to discuss how their profits would be split. Breslow initially suggested splitting the profits equally, but according to him, Trump replied, "I don't do 50–50." Trump received 60 percent of the profits to Breslow's 40 percent. Breslow said, "The game wasn't sellable without Donald Trump. He could have squeezed me for even 80–20. He knew he was in the driver's seat." Breslow requested that Trump promote the game at the American International Toy Fair and at the Milton Bradley factory, which Trump agreed to do.

Trump: The Game was unveiled during an event at Trump Tower on February 7, 1989. The game was expected to retail for $25. Trump said at the event that his undisclosed percentage of the game's revenue would be donated to charities that benefited cerebral palsy and AIDS research, as well as help for homeless people. Milton Bradley executives, who had worked with Trump for more than a year on the game, were surprised as they had not been aware of Trump's charitable intentions. The game was patterned after Monopoly, and based on Trump's career and his 1987 book, The Art of the Deal. Trump, who received input in developing the game with Milton Bradley game specialists, said, "I didn't want a game based solely on chance. I wanted a game based on talent. And I wanted to teach people if they have business instincts. It's great if they can learn that from a game instead of having to go out and lose your shirt." Trump also said, "I really like the game. It's much more sophisticated than Monopoly, which I've played all my life." George Ditomassi, the president of Milton Bradley at the time, declined to specify how much money the company paid Trump to name the game after him, although Ditomassi estimated that the game's donated proceeds would total $20 million.

At the time of its announcement, there was speculation as to whether Trump: The Game could have an effect on sales of Monopoly and other board games. Phil Orbanes, senior vice president of research and development for Parker Brothers, said that Trump's game "is not the kind of thing you want to pull out on the spur of the moment when grandma comes over. It can leave you exhausted and feeling like you don't want to play again. As accurate as it may be at capturing the feeling of insecurity in the real world, the game doesn't give you a feel-good experience, which is the purpose most people rely on for playing games." Breslow, who had no faith that the game would become as popular as Monopoly, later said that a "huge percentage" of Trump board games "were never taken out of the box. It was bought as a gift item, a novelty, a curiosity. Trump got that. He had zero interest in how the game played."

In March 1989, Vegas World casino owner Bob Stupak challenged Trump to play a round of Trump: The Game, with Stupak wagering a $1 million bet. Trump declined, saying, "It's always possible to lose, even for someone who's used to winning." Stupak then ran full-page ads in the New York Post and The Press of Atlantic City that publicly challenged Trump to play the game with him. Trump did not accept the challenge.

Trump: The Game was launched in May 1989, with the tagline, "It's not whether you win or lose, it's whether you win!" Trump appeared in a television commercial for the game. Trump and Milton Bradley hoped the game would sell two million copies, although the game ultimately sold poorly. By August 1990, Trump acknowledged that the game may have been too complicated. The rulebook was more than 12 pages long. Trump said the game had sold 800,000 units.

Ditomassi said about the game's failure, "The game was just nailed to the shelf." Ditomassi felt that one reason for the game's poor sales was that it had the Trump name and customers were unaware of its revenue being partially donated to charity: "They felt perhaps this was going to be something that a millionaire would make some money on." The game's television commercial was changed to include a new voice-over which stated: "Mr. Trump's proceeds from Trump: The Game will be donated to charity." However, sales of the game failed to increase. It was also believed that sales suffered because the game was misleadingly marketed as a Monopoly knockoff. Analysts also believed that the public had grown tired of Trump. Orbanes said that games such as Trump: The Game "were too heavily involved with what appeared to be high-level finance. That's too intimidating to most people."

In May 1991, Trump won a lawsuit brought against him by Stuart Ross, a Manhattan attorney who said he had been hired to serve as an agent in licensing the game. Ross said he had suggested the idea of a board game to Trump, and that he was promised 25 percent of the game's royalties. Ross had sought $200,000 in the lawsuit. Trump had testified that he never made a contract with Ross, and that the game's royalties—$866,800—had already been donated to charity after being deposited with the Donald J. Trump Foundation, although he did not provide records to prove his claim.