
Ivylise Simones
Until the election, we’re bringing you “The Trump Files,” a daily dose of telling episodes, strange but true stories, or curious scenes from the life of GOP nominee Donald Trump.
In 1995, five years after his business empire nearly collapsed under massive debt, Donald Trump was finally righting the ship. He’d sold off costly assets like his mega-yacht and money-losing airline, gone through two bankruptcies, and gotten debt relief by giving his creditors partial ownership of some of his properties. But the three casinos he still controlled—the Taj Mahal, the Trump Plaza, and the Trump Castle—were still deeply in debt.
So Trump figured out a way to erase that debt—at least for himself. He created Trump Hotels and Casino Resorts, a publicly traded company that operated the Trump Plaza. For about six months, it was a success. The company’s stock shot up from $14 to $35 a share, putting Trump back on the Forbes list of America’s 400 wealthiest people and helping him pay down $88 million of his personal debt, according to the Washington Post’s Michael Kranish and Marc Fisher in their book, Trump Revealed. “The IPO of Trump Hotels was what finally fueled Trump’s comeback,” wrote Fortune this March.
Then Trump sprung the trap. He used the company to buy the Taj Mahal and the Trump Castle, effectively purchasing the casinos from himself at a price that he set. “The company bought his Castle for $100 million more than analysts said it was worth,” the Post reported in June. “Trump pocketed $880,000 in cash after arranging the deal.” The two properties were also $1.7 billion in debt, and that debt suddenly belonged to Trump Hotels instead of Trump himself.
By the end of 1996, Trump Hotels stock was worth just $12. It eventually crashed down to 17 cents a share. “A shareholder who bought $100 of DJT [the company’s ticker symbol] shares in 1995 could sell them for about $4 in 2005,” Kranish and Fisher wrote. The company lost more than a billion dollars and filed for bankruptcy in 2004 and 2009. But even as its value collapsed over the years, the company paid Trump a total of $82 million by Fortune‘s estimate, covered the cost of entertaining his VIP guests, signed contracts to buy other Trump products, and even employed then-26-year-old Ivanka Trump on its board.
Donald and Ivanka resigned from the company’s leadership in 2009 in protest of the bondholders’ demands to go into Chapter 11 bankruptcy again. But despite making a killing while leaving his shareholders in the lurch, he doesn’t have any regrets. “All I can say is I wasn’t representing the country,” he told the Post. “I wasn’t representing the banks. I wasn’t representing anybody but myself.”
Read the rest of “The Trump Files”:
- Trump Files #1: The Time Andrew Dice Clay Thanked Donald for the Hookers
- Trump Files #2: When Donald Tried to Stop Charlie Sheen’s Marriage to Brooke Mueller
- Trump Files #3: The Brief Life of the “Trump Chateau for the Indigent”
- Trump Files #4: Donald Thinks Asbestos Fears Are a Mob Conspiracy
- Trump Files #5: Donald’s Nuclear Negotiating Fantasy
- Trump Files #6: Donald Wants a Powerball for Spies
- Trump Files #7: Donald Gets An Allowance
- Trump Files #8: The Time He Went Bananas on a Water Cooler
- Trump Files #9: The Great Geico Boycott
- Trump Files #10: Donald Trump, Tax-Hike Crusader
- Trump Files #11: Watch Donald Trump Say He Would Have Done Better as a Black Man
- Trump Files #12: Donald Can’t Multiply 17 and 6
- Trump Files #13: Watch Donald Sing the “Green Acres” Theme Song in Overalls
- Trump Files #14: The Time Donald Trump Pulled Over His Limo to Stop a Beating
- Trump Files #15: When Donald Wanted to Help the Clintons Buy Their House
- Trump Files #16: He Once Forced a Small Business to Pay Him Royalties for Using the Word “Trump”
- Trump Files #17: He Dumped Wine on an “Unattractive Reporter”
- Trump Files #18: Behold the Hideous Statue He Wanted to Erect In Manhattan
- Trump Files #19: When Donald Was “Principal for a Day” and Confronted by a Fifth-Grader
- Trump Files #20: In 2012, Trump Begged GOP Presidential Candidates to Be Civil
- Trump Files #21: When Donald Couldn’t Tell the Difference Between Gorbachev and an Impersonator
- Trump Files #22: His Football Team Treated Its Cheerleaders “Like Hookers”
- Trump Files #23: The Trump Files: Donald Tried to Shut Down a Bike Race Named “Rump”
- Trump Files #24: When Donald Called Out Pat Buchanan for Bigotry
- Trump Files #25: Donald’s Most Ridiculous Appearance on Howard Stern’s Show
- Trump Files #26: How Donald Tricked New York Into Giving Him His First Huge Deal
- Trump Files #27: Donald Told Congress the Reagan Tax Cuts Were Terrible
- Trump Files #28: When Donald Destroyed Historic Art to Build Trump Tower
- Trump Files #29: Donald Wanted to Build an Insane Castle on Madison Avenue
- Trump Files #30: Donald’s Near-Death Experience (That He Invented)
- Trump Files #31: When Donald Struck Oil on the Upper West Side
- Trump Files #32: When Donald Massacred Trees in the Trump Tower Lobby
- Trump Files #33: When Donald Demanded Other People Pay for His Overpriced Quarterback
- Trump Files #34: The Time Donald Sued Someone Who Made Fun of Him for $500 Million
- Trump Files #35: Donald Tried to Make His Ghostwriter Pay for His Book Party
- Trump Files #36: Watch Donald Shave a Man’s Head on Television
- Trump Files #37: How Donald Helped Make It Harder to Get Football Tickets
- Trump Files #38: Donald Was Curious About His Baby Daughter’s Breasts
- Trump Files #39: When Democrats Courted Donald
- Trump Files #40: Watch the Trump Vodka Ad Designed for a Russian Audience
- Trump Files #41: Donald’s Cologne Smelled of Jamba Juice and Strip Clubs
- Trump Files #42: Donald Sued Other People Named Trump for Using Their Own Name
- Trump Files #43: Donald Thinks Asbestos Would Have Saved the Twin Towers
- Trump Files #44: Why Donald Threw a Fit Over His “Trump Tree” in Central Park
- Trump Files #45: Watch Trump Endorse Slim Shady for President
- Trump Files #46: The Easiest 13 Cents He Ever Made
- Trump Files #47: The Time Donald Burned a Widow’s Mortgage
- Trump Files #48: Donald’s Recurring Sex Dreams
- Trump Files #49: Trump’s Epic Insult Fight With Ed Koch
- Trump Files #50: Donald Has Some Advice for Citizen Kane
- Trump Files #51: Donald Once Turned Down a Million-Dollar Bet on “Trump: The Game”
- Trump Files #52: When Donald Tried to Shake Down Mike Tyson for $2 Million
- Trump Files #53: Donald and Melania’s Creepy, Sex-Filled Interview With Howard Stern
- Trump Files #54: Donald’s Mega-Yacht Wasn’t Big Enough For Him
- Trump Files #55: When Donald Got in a Fight With Martha Stewart
- Trump Files #56: Donald Reenacts an Iconic Scene From Top Gun
- Trump Files #57: How Donald Tried to Hide His Legal Troubles to Get His Casino Approved
- Trump Files #58: Donald’s Wall Street Tower Is Filled With Crooks
- Trump Files #59: When Donald Took Revenge by Cutting Off Health Coverage for a Sick Infant
- Trump Files #60: Donald Couldn’t Name Any of His “Handpicked” Trump U Professors
- Trump Files #61: Watch a Clip of the Awful TV Show Trump Wanted to Make About Himself
- Trump Files #62: Donald Perfectly Explains Why He Doesn’t Have a Presidential Temperament
- Trump Files #63: Donald’s Petty Revenge on Connie Chung
- Trump Files #64: Why Donald Called His 4-Year-Old Son a “Loser”
- Trump Files #65: The Time Donald Called Some of His Golf Club Members “Spoiled Rich Jewish Guys”
- Trump Files #66: “Always Be Around Unsuccessful People,” Donald Recommends
- Trump Files #67: Donald Said His Life Was “Shit.” Here’s Why.
- Trump Files #68: Donald Filmed a Music Video. It Didn’t Go Well.
- Trump Files #69: Donald Claimed “More Indian Blood” Than the Native Americans Competing With His Casinos
- Trump Files #70: Donald Has Been Inflating His Net Worth for 40 Years
- Trump Files #71: Donald Weighs In on “Ghetto Supastar”
- Trump Files #72: The Deadly Powerboat Race Donald Hosted in Atlantic City
- Trump Files #73: When Donald Fat-Shamed Miss Universe
- Trump Files #74: Yet Another Time Donald Sued Over the Word “Trump”
- Trump Files #75: Donald Thinks Exercising Might Kill You
- Trump Files #76: Donald’s Big Book of Hitler Speeches
- Trump Files #77: When Donald Ran Afoul of Ancient Scottish Heraldry Law
- Trump Files #78: Donald Accuses a Whiskey Company of Election Fraud
- Trump Files #79: When Donald’s Anti-Japanese Comments Came Back to Haunt Him
- Trump Files #80: The Shady Way Fred Trump Tried to Save His Son’s Casino
- Trump Files #81: Donald’s Creepy Poolside Parties in Florida
- Trump Files #82: Donald Gives a Lesson in How Not to Ski With Your Kids
- Trump Files #83: Listen to Donald Brag About His Affairs—While Pretending to Be Someone Else