In 1988, shortly after Donald Trump published his first book, “The Art of the Deal,” Jeffrey Breslow found himself in Trump Tower, in the mogul’s office, setting up a board game and inviting the billionaire to play.

Regulars at Labyrinth Games and Puzzles on Capitol Hill roll the dice with "Trump: The Game," bidding on real estate and trying to muster their inner “Donald.” (Erin Patrick O'Connor/The Washington Post)

Breslow, for decades one of the nation’s leading game inventors, was prepared to get down on the floor and pit his strategic wiles against the guy whose picture would be on the box of Trump: The Game, a Monopoly-inspired race to get very rich, very fast.

Breslow started to explain his prototype of the game he wanted Trump to endorse, but Trump cut him off: “I like it — what’s next?”

What came next was a lightning-fast negotiation, a promotional blitz and the sale of about a million units, giving American consumers an early opportunity to play at the cutthroat gamesmanship that — at least, according to the rules booklet — constituted Trump’s business philosophy.

Nearly three decades later, Trump: The Game is a collector’s item. It’s a tempting purchase on eBay — whose friends wouldn’t be impressed? But would the game provide any insight into how the Republican presidential front-runner operates? The Washington Post took the game, bought on the auction site for $28, to some of the capital’s most devoted gaming nerds, at Labyrinth Games & Puzzles on Capitol Hill. The shop doesn’t carry the Trump game because it is out of print, but owner Kathleen Donahue had heard about the game. Its reputation isn’t too different from Trump’s: Winning requires ruthlessness.

“I really like mean games,” Donahue said, “because I’m so nice in real life.” Her 11-year-old son, sitting in the corner, rolled his eyes. Many of Donahue’s clients are political nerds, like the customers who volunteered to play her in Trump: The Game — Teddy Woodhouse, a 25-year-old executive assistant, and Shane Russell, a 28-year-old software developer and political card game creator.

Trump’s game asks players to move T-shaped tokens around the board while they try to buy up luxury hotels, casinos and other big-ticket items.

Russell read through the rules. The object: Bluff opponents into spending foolishly while you buy low and sweep up big profits. As a signed letter from Trump on the back of the rules states, “The player with the most money wins!”

First they had to hand out the money. Each player begins with $500 million. The smallest denomination of paper cash is $10 million.

“Chump change!” Woodhouse said. He picked up the flimsy bills and found a familiar face on every one. He corrected himself: Make that “Trump change.”


Trump, Donald Trump's Monopoly-inspired board game. The GOP front-runner’s face is on the currency. (Nicole Crowder/The Washington Post)
The deal

Breslow was under no illusion that Trump: The Game would ever join Monopoly as a permanent staple in American dens. “A huge percentage of those games were never taken out of the box,” he says. “It was bought as a gift item, a novelty, a curiosity. Trump got that. He had zero interest in how the game played.”

Breslow based the game more on Monopoly and his own previous inventions than on any intimate knowledge of Trump’s business style. But the lessons preached in “The Art of The Deal” also played a role.

Armed with the okay from Trump, Breslow sold the game to Milton Bradley, one of the game industry’s biggest players, and returned to Trump for a one-on-one discussion about how to split the proceeds.

It was a quick meeting. “I pointed to my chest and said ‘50,’ ” Breslow says, “and I pointed to him and said, ‘50.’ Trump said, ‘I don’t do 50-50.’ He pointed to his chest and said, ‘60’ and at me and said, ‘40.’ And I said, okay, we got a deal.”

Not that Breslow had much choice: “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 had one ask. He wanted Trump to promote the game at the industry showcase, the Toy Fair, and at Milton Bradley’s factory. Trump was happy to do both.

He even appeared in a TV commercial, a clunky bit of awkward ’80s salesmanship in which cheerful young people offer banter like this:

“I wonder what Trump’s game is this time!”

“What’s your game, Donald?

The mogul himself replies, “My new game is Trump: The Game.”

In the commercial and on the game’s box, the tag line is classically Trumpian: “Because it’s not whether you win or lose, it’s whether you win.”

When Trump flew up to the plant in Massachusetts for a photo op, he signed autographs and told workers on the factory floor that “if you don’t do well at this game, you should stay on your 9-to-5.”

The hype won plenty of publicity. Dueling reviewers pronounced the game pretty good (Chicago Tribune: “It’s a sophisticated acquire-and-deal game”) and not so hot (Los Angeles Times: “not the kind of thing you want to pull out on the spur of the moment when grandma comes over.”)

The interest was so keen that a Vegas poker player took out full-page newspaper ads offering Trump $1 million to play the game with him. Trump declined.

Your move, player

The game on Capitol Hill was heated from the first bid. Woodhouse plopped down $240 million to claim the International Golf Course. The next player landed on the hotel. When a player lands on a property, it goes up for auction. Russell was about to buy the hotel for $60 million when Donahue pulled out the game’s signature card.

“YOU’RE FIRED!” it declares in thick red letters. The card blocked Russell from the bidding. But before Donahue could claim the property, Woodhouse laid a “YOU’RE FIRED!” card on her, winning his second property before the others had anything to their names.

“I feel the ethos of Trump!” he announced. “I feel so good right now. I can go play golf, and then go lounge in my hotel.”

Donahue sulked. “I just want to fire people all of the sudden,” she said. She turned to her employee behind the counter: “Melissa, you’re fired!”

Melissa rolled her eyes. The game went on. The players concluded this wasn’t a particularly good game, compared with the complex strategy games popular at the store. They liked that it was shorter than Monopoly and they liked the “Trump tips,” bits of Trumpian wisdom written on each “Trump card” (“I would fire the person most likely to fire me.”) The card THE DONALD returns you to the bidding if you have been fired.

The players found themselves uttering sentences such as “I had interests lying on that office building that are undisclosed!” and “I was going to make a deal with you, but now I’m just going to steal it.”


“You’re Fired” cards knock other players out of the bidding on a property. (Nicole Crowder/The Washington Post)

Each player moves around the board with a T-shaped token. Each die has a “T” instead of a six. (Nicole Crowder/The Washington Post)

After an hour and a half, the final property — “luxury residence” — went up for sale. Donahue bid $200 million. Woodhouse put up $250 million. Russell offered just $10 million.

But then Donahue fired Woodhouse. Russell fired Donahue. Donahue came back with THE DONALD. Russell fired her again. The luxury residence was Russell’s for only $10 million.

But in the final tally, Russell had $1.19 billion and Woodhouse had $1.22 billion, achieved by betting high and firing anyone in his way.

“I feel victorious!” he said. “But uneasily so. I think there are some emotional sacrifices you have to make to play the game well.”

Game over

Trump and Breslow say Trump donated his royalties from the game to charity. “The game was just ego to him, one more promotion,” Breslow says.

The game sold well enough that in 2004, capitalizing on the popularity of Trump’s “The Apprentice” show on NBC, Breslow created a second Trump game. Trump showed up for a promotional event at Trump Tower, surrounded, as the original press release put it, “by 10 beautiful Trump Management models in Marc Bouwer designs.” Trump selected five people from the crowd to “enter the golden money machine and grab as much Trump money as they can in 15 seconds.” The winner of that exercise would get a free stay at Trump’s Taj Mahal resort in Atlantic City.

It didn’t help. The second game — despite, in Breslow’s view, being a better play than the first — bombed, he says.

Breslow says he doesn’t know yet whether he’d vote for Trump. He won’t vote for Hillary Clinton. “We have 350 million people and this is what we’re down to — a liar and a demagogue,” he says. “But my experience with him was terrific. If he somehow wins, maybe there’s a Trump: The President game.”