The Weirdest Things Donald Trump Ever Bought

Luxury cars, helicopters, private planes, penthouses — these are the trappings of lowly plebs, shamefully known as — ew, gross! — millionaires. But as President Donald J. Trump is sure to tell anyone within earshot, he is something much better: a billionaire. As such, he spends his money on the one luxury item for which the super-rich really go wild: more money.

Interestingly, after a series of bankruptcies, the Trump business empire has become as much about branding as legitimate real estate holdings. So when The Donald invests, sometimes it's a bit of a mirage, with his name on it, and very little skin in the game. But if you've been following his illustrious career closely, that's always been a key to his investment playbook. As the famous line from The Producers goes, "never put your own money in the show!"

Today, he "owns" everything from luxury golf courses to board games with his logo emblazoned. And Trump's net worth sits anywhere between one and four billion dollars. No one really knows for sure. Forbes recently put his net worth at $2.5 billion — after you shave a billion off the top in debts. He's up, then he's down. But he's never boring, and he's always been a big spender. Here are some of his choicest purchases.

Donald Trump buys portraits of himself

In 2019, Donald Trump's ostensible charitable organization known as the Trump Foundation was basically declared a front by the New York Supreme court, according to The New York Times. The foundation's money was spent on events such as glamorous galas that raised money for things like Trump's run through the Republican primaries in 2016, and uh, New York state apparently does not consider a billionaire's political ambitions a legitimate locus of "charity." So, as attorney general Letitia James announced on the AG's website, Trump had to pay $2 million in damages.

The best part of the case though called out Trump's next-level selfie game. According to the ruling, "the Foundation paid for a portrait of Mr. Trump that cost $10,000."

Trump was forced to pay back the money, but apparently, he only bought that portrait in the first place because no one else made a bid, according to Bloomberg. Trump was literally just saving face. His face. Another portrait of Trump was also supposedly successfully auctioned for $60,000 in 2013. Trump crowed about it on Twitter, but his disgraced former attorney Micheal Cohen alleges Trump also used his foundation to front that purchase too, according to The Art Newspaper.

Donald Trump scooped up a lot of one Covid-19 treatment

Something extremely exciting happened to Donald Trump in 2016. Yes, yes, he became the most powerful man on the planet. But just as fun for a billionaire spendthrift like "The Donald," he also got his hands on the world's most bottomless wallet: the US Treasury.

Then the coronavirus struck in 2020. There are limited options to treat the suite of mysterious symptoms that accompany Covid-19. The first approved therapy in the US, however, is called remdesivir, and the Trump administration moved swiftly to buy the entire global supply, according to The Guardian. The US gobbled up over 500,000 doses in an extension of the president's campaign promise to enact an "America First" agenda. 

"President Trump has struck an amazing deal to ensure Americans have access to the first authorized therapeutic for Covid-19," said the US health and human services secretary, Alex Azar. "To the extent possible, we want to ensure that any American patient who needs remdesivir can get it." Of course, that's not enough doses for the millions of US cases overall but could cover the most severe, with a reported cost of about $3,200 per six-dose treatment.

The Tour de Donald Trump

In 1989 the shady world of competitive cycling felt like the perfect place for then real-estate scion Donald Trump to expand his New York-area branding empire. Years before doped athletes like Lance Armstrong showed the world just how corrupt going for a long bike ride can be, Trump decided to bring the show to the tri-state area. "I think this is an event that can be tremendous in the future, and can really very much rival the Tour De France," Trump told NBC Sports.

The 837-mile race was dreamed up by a business associate of Trump named Billy Packer and originally conceived to run from Manhattan to Atlantic City. As Politico recalled, it would be the glorious "Tour De Jersey," and rival its snooty French counterpart, thought all involved. But before meeting with Trump, Packer had a better idea, and decided he'd pitch the race as the "Tour De Trump." And you gotta say, the man understood his audience. 

The five-day jaunt eventually paid out $250,000 in prize money including $50,000 for the winner, according to The New York Times (via The Washington Post). The inaugural race featured the world's best riders but ended, predictably, in controversy, with a dispute about the real winner, according to The New York Times. The Tour De Trump lasted until 1991, at which point "the DuPont Corporation took over the sponsorship," according to Gran Fondo Guide. The race was run until 1996 when Lance Armstrong was its final winner.

Donald Trump? More like Donald-opoly

Also in 1989, Donald Trump made a fitting investment considering his holdings from Wall Street to the Boardwalk of Atlantic city and created his own version of Monopoly. And you won't guess whose face is on the money! The Milton Bradley-manufactured diversion even had a tagline befitting its namesake: "It's not whether you win or lose, but whether you win!," according to Vanity Fair.

Like Monopoly, the point of the game is accruing cash. The rules "read like a fascinating window into his gold-plated psyche," quips Vanity Fair. Or, as is further spelled out in Trump Speak, you need to stack millions to win, but "I'm talking about hundreds of millions of dollars ... Live the fantasy! Feel the power! Make the deals!" The game pieces are all little Ts, the dice are emblazoned the same. Trump: The Game was also updated years later to include his popular "you're fired!" catchphrase from The Apprentice. It can still be found on Amazon and goes for nearly $100!

Maybe the best part of Trump: The Game though is the moral ambiguity baked into the ruleset: "You cannot lie to another player or intentionally break a promise. Of course, some situations may be open to interpretation." So, pro-tip for your next game night, the real key to winning bigly here is, as another great New Yorker once put it, "it's not a lie if you believe it."

Donald Trump: The Ride

Donald Trump isn't really known for being super low-key about his assets. He's at times claimed a net worth of $10 billion, according to CNN. However, his actual value has also been estimated as low as just over $1 billion, according to an analysis of his financial disclosure records, also by CNN. Even Trump admits his wealth is subject to interpretation, telling Bloomberg his value "goes up and down with markets and with attitudes and with feelings, even my own feelings."

But one cold hard asset Trump hasn't been very Trumpy about though is the storied Friedsam Memorial Carousel in Central Park, which he owns and operates under Trump Carousel LLC. And surprisingly, the attraction does not feature any of his typically ostentatious signage. Rides go for a humble $3, says CNN, cash only of course, and according to his own disclosures, it can rake in $600,00 in one year for The Donald.

Trump was derided by Rolling Stone as losing "more money than anyone in America between 1985-1994." And yet Trump's other nearby ice rinks, including Wollman Rink and Lasker Rink, also helped him pull in $59 million in park attraction revenue, in only three years, according to The Washington Post. There's always money in the banana stand.

Get schooled by Donald Trump

When one thinks about higher education, Donald Trump isn't always the first name to come to mind. After all, this is a man accused of hiring someone to take his SATs for him — an allegation lodged by his salty niece in her tell-all book Too Much and Never Enough: How My Family Created the World's Most Dangerous Man, via BBC News.

Trump sought to make his mark in the realm of accredited learning anyway, with Trump University, founded in 2005, according to the Center For American Progress. This turned out to be an incredibly expensive blunder for the more "street-smart" Trump, when a federal judge finalized a $25 million settlement against the "sham university" in 2018, according to USA Today

Former students organized a class-action lawsuit against the school alleging they'd paid $35,000 under duress of "high-pressure sales tactics," for classes taught by "unqualified instructors," according to The New York Times. Trump had initially promised to fight the suit, but as the prospect of his election in 2016 went from far-fetched to plausible, he had a change of heart and settled, "without an acknowledgment of fault or liability," according to his attorney. 

Donald Trump gambled on a casino

Speaking of licenses to print money, how about the casino business! What other product offers consumers the chance to addictively piddle away their life-savings, in return for ... absolutely nothing! Hope maybe? Then again, that isn't really a product. And you could now say the same about Donald Trump's famed Plaza in Atlantic City. If you've been there any time in the last few years, you definitely get the Zach Galifianakis joke about a cricket riding a tumbleweed.

Trump opened his casino in 1984, which he ran until 2014, just two years after Hurricane Sandy "captured Atlantic City and refused to let go," according to The New York Times, doing its nasty work on the local economy. Trump's Plaza was sold in bankruptcy in 2016 and by 2020 the mayor of Atlantic City, Marty Small, was on a personal crusade against the vacant palace. "My administration's goal is to tear Trump Plaza down," Small told NJ.com. "It's an embarrassment, it's a blight on our skyline, and that's the biggest eyesore in town."

Billionaire Carl Icahn now owns The Plaza and wanted to keep parts standing, but mayor Small isn't having it. Debris is reportedly now falling off the facade and plans to fix the issue are not progressing quickly enough for the displeased city leader, again according to NJ.com, calling The Plaza an "imminent hazard." Trump's former pearl on the Atlantic is set to be imploded, likely sometime in 2021.

Want 'hospitality installations'? Try Trump Home Collection

Back in 2013, this Nicki Swift scribe spent the day inside Donald Trump's Fifth Avenue penthouse, waiting for future First Lady Melania Trump to share the wonders of her now-defunct skincare line. As an aside, the line's primary ingredient, perhaps not surprisingly, is caviar. "Caviar in skin products is a really interesting ingredient, partially because I'm not actually sure what it is, and I'm not sure anyone does," New York dermatologist Sejal Shah told Racked.com. But when Melania finally emerged into the great room of her palace, her skin was indeed glowing.

Anyway, Trump's home was exactly on-brand. The man goes broke for baroque, or as The Trump Home Collection puts it, "handcrafted to perfection." But actually, Trump's furniture line, which is a blend of mid-century modern with a hint of Victorian panache, has little to do with the Louis XIV-level orgy of gilded molding that characterizes his $100 million three-story Manhattan crib. 

Trump "Home" seems to be more marketed at commercial enterprises, which the website calls "hospitality installations" — fancy talk for hotels. The line is manufactured mostly in Germany and Turkey, according to The Washington Post, in an effort to point out the "America First" oligarch outsources manufacturing like everybody else. Oddly, you can't even see what this stuff even costs via his website without handing over your entire identity to create a login. However, according to Furniture Today, Trump-branded dining tables can go for as much as $21,000 a pop.

Stormy Daniels' silence can't be bought

You get what you pay for, goes the old maxim. And when you have your shady lawyer fork over a bag of cash to keep a porn star quiet, you get it good and hard.

The saga of Donald Trump and Stormy Daniels is twisty and fun. They meet. They bone. According to the account Daniels gave In Touchit's casual. But when Trump got a lot farther than anyone expected in the 2016 Republican primary, the affair became a loose end. Enter Trump's lawyer-slash-fixer, recent Otisville Correctional Facility graduate, Micheal Cohen, with $130,000 in hush money to keep the adult actress from reaching out to the press, according to The Wall Street Journal

Daniels took the cash and squawked anyway. She went on 60 Minutes in 2018 and claimed that years earlier a man threatened her and her child in a parking lot about her tryst with the married TV star. The cat was out of the bag and In Touch finally published the interview that'd been shelved since 2011 where Daniels claims, "I can definitely describe his junk perfectly."

Daniels must've thought Trump short-changed her because she then dropped a tell-all memoir, called Full Disclosure, where she delivered that long-promised dong description. "He knows he has an unusual penis," Daniels writes (via The Guardian). "It has a huge mushroom head. Like a toadstool." This is no doubt the worst six figures Trump ever spent.

Donald Trump threw his hat in the ring

The sport of boxing has always been deeply corrupt. Fixes, dives, rigged judging — you name it. But it's also a glorious spectacle where everybody exaggerates for cash. Enter Donald Trump.

Trump jumped into boxing in the late 1980s as "Iron" Mike Tyson was punching heads right off people's shoulders. And of course, Trump is "a natural promoter," as another famed fight hyper told The Telegraph. The Donald hosted fights at his Plaza in Atlantic City, including Tyson's incredible heavyweight unification bout with Michael Spinks in 1988. Spinks was so scared he didn't even want to leave his dressing room and was then brutally knocked out in only 91 seconds. Trump got his money's worth, and even got a pre-bout introduction from the ring announcer — a little shout-out for hosting. 

His foray into the "sweet science" wasn't always sweet. Yahoo! Sports reported other promoters claimed he "swindled" them out of $2.5 million in 1991. Trump and Tyson allegedly fell out, too. According to a 2005 hit-piece biography TrumpNation: The Art of Being the Donald (via Yahoo! Sport), the champ supposedly marched into Trump's office and yelled, "are you f***ing my wife?"

Speaking of TrumpNation, Trump went on to sue the book's author for $5 billion for claiming he was merely a millionaire, according to The Washington Post. Two bank estimates in the deposition that followed showed Trump's net worth, though exaggerated, was over $1 billion, according to CBS News. (As ABC News reported, the lawsuit was dismissed in 2009.) 

Donald Trump went on a real estate shopping spree

"I'm the king of debt. I'm great with debt. Nobody knows debt better than me," Donald Trump told CBS News in 2016. And his creditors might agree, given he has filed for business bankruptcy at least four times, according to the American Bankruptcy Institute. But what Trump was saying here is, essentially, that he's smart. He borrows money, finances deals, and if they go bad, bankruptcy law lets him skate on some of the tab.

That strategy changed dramatically however in 2006 when Trump began plunking down mountains of cold hard cash up-front in a dizzying decade-long real-estate buying spree that totaled $400 million, according to the Chicago Tribune. This included nearly $80 million for golf courses in Ireland and Scotland in 2014, homes in Beverly Hills, a winery in Virginia, and five more courses on the East Coast of the US. 

There's been a lot of speculation regarding this sudden cash strategy, but nobody really has the receipts. Eric Trump allegedly told a golf writer the family business is rich in Russian funding, according to The Hill. However, the story is based entirely on hearsay and Eric publicly called it "fabricated" via Twitter. On the record, DJT's son claims the switch in strategy is because The Donald was tired of losing his shirt on debt like he did in the '90s. "Those lessons undoubtedly shaped his business approach and the conservative nature of how we conduct business today," Eric told The Washington Post.

Donald Trump made time for Ronald Reagan's watch

Before he decided he'd become king of the Republicans in 2016, Donald Trump was a Democrat for eight years in the 2000s, according to POLITIFACT. His party affiliation has been erratic over years, and once even included the Independence Party. The flip-flopping also includes some uneven admiration for "The Gipper" himself, Ronald Reagan.

Trump picked up Reagan's wristwatch at auction in 1999 for a mere $7,000, according to the truly fun watch blog, A Blog To Watch. The timepiece itself is a fairly pedestrian 32mm-wide Colibri Quartz and was, "perhaps among the least valuable ones at the auction event." It was rather the frenemy who wore it, which gave it value for Trump. 

Trump was a registered Republican in 1987, but that same year, in his book The Art of The Deal (via Politico), he wrote Reagan was "so smooth, so effective a performer" that "only now, seven years later, are people beginning to question whether there's anything beneath that smile." Maybe that was because, as The Washington Post harshly chronicles, Reagan's team viewed Trump's "large ego" with caution and "spent much of the 1980s trying to gently reject the mogul's self-aggrandizing overtures." As president though, The Donald admiringly shared an old photo of himself, shaking hands with the 40th president. Reagan is pictured keeping his watch hand at a safe distance, but Trump still pocketed it.