‘Shem’s Idle Notes’

Donald John Trump, Sr. (born June 14, 1946) is an American business magnate, television personality and author. He is the chairman and president of The Trump Organization and the founder of Trump Entertainment Resorts. Trump’s extravagant lifestyle, outspoken manner and role on the NBC reality show The Apprentice have made him a well-known celebrity who was No. 17 on the 2011 Forbes Celebrity 100 list. Besides his world-famous business prowess, Donald Trump has every reason to be proud of himself. He managed to convince President Obama to release his birth certificate, ending the debate over whether he was legally fit to lead the country. But not everything the Donald has put his name behind has succeeded.  Here, TIME Magazine takes a look at some of his gambles that didn’t go as planned.

10.  The Middle East ‘Policy’

Trump once suggested that the US "take an oil field” in the Middle East as a way of "reimbursing ourselves” as expenses incurred during the wars. When recently discussing oil prices on air with ABC’s George Stephanopoulos, Donald Trump blustered on about the scheming malfeasance of OPEC and the kingdom of Saudi Arabia. Trump insisted the U.S. could leverage its military supremacy to persuade OPEC to lower prices. In his words: "I’m going to look ‘em in the eye and say, ‘Fellas, you’d have your fun. Your fun is over.’” But this rather naive suggestion of bullying one of the U.S.’s most longstanding and essential allies in the Middle East was comparatively harmless when set against his next suggestion. Trump bemoaned U.S. costs sustained during its wars in the Middle East and floated the idea of "taking” Iraqi oil. Stephanopoulos countered incredulously, "So, we steal an oil field?” Trump responded, "Excuse me. You’re not stealing anything. You’re taking — we’re reimbursing ourselves.” Given how many U.S. leaders have had to stress to their Middle East interlocutors that they’re not in it simply for the oil, Trump would be starting off regional relations on pretty slippery ground.

9. Trump Casinos

In February 2009, Trump Entertainment Resorts Inc. filed for Chapter 11 bankruptcy protection for the third time in a row — an extremely rare feat in American business. The casino company, founded in the 1980s, runs the Taj Mahal, the Trump Plaza and the Trump Marina. All three casinos are located in Atlantic City, N.J., where the gambling industry has faced a decline in tourists who prefer gambling in Pennsylvania and Connecticut instead. Trump defended himself by distancing himself from the company, though he owned 28% of its stock. "Other than the fact that it has my name on it — which I’m not thrilled about — I have nothing to do with the company,” he said. He resigned from Trump Entertainment soon after that third filing, and in August of that year he, along with an affiliate of Beal Bank Nevada, agreed to buy the company for $100 million.

8. The China Connection

Well, Trump ventured into a clothing line, claiming "The problem with our country is we don’t manufacture anything anymore,” Donald Trump told Fox News a year ago. "The stuff that’s been sent over from China,” he complained, "falls apart after a year and a half. It’s crap.” That very same Donald Trump has his own line of clothing, and it’s made in ... China. (O.K., O.K. — not all of it. Salon, which reported this intriguing, head-scratching fact, notes that some of his apparel is from Mexico and Bangladesh.

7. Trump: The Game

In 1989, the Donald teamed up with Milton Bradley to release Trump: The Game, a Monopolyesque board game in which three to four players must buy and sell real estate and try to trump one another in business deals. A year later Trump admitted the game was vastly underselling the predicted 2 million units he and the toy company had hoped for. Not one to abandon ridiculous ideas, Trump revived the game 15 years later after his success on The Apprentice, making sure to incorporate the series catchphrase "You’re fired!” into the game. Other updated features included a sterner-looking Trump on the box cover, somewhat simpler rules and cards with business tips. Enduring feature? The considerable tack factor of a Donald Trump board game.

6. Trump Mortgage

In April 2006, Trump announced that, after years in the real estate business, he was launching a mortgage company. He held a glitzy press conference at which his son Donald Jr. predicted that Trump Mortgage would soon be the nation’s No. 1 home-loan lender. Trump told CNBC, "Who knows more about financing than me?” Apparently, plenty. Within a year and a half, Trump Mortgage had closed shop. The would-be lending powerhouse was done in by timing (the housing market cratered in 2007) and ironically enough, given Trump’s Apprentice TV show, poor hiring. The executive Trump selected to run his loan company, E.J. Ridings, claimed to have been a top executive at a prestigious investment bank. In reality, Ridings’ highest role on Wall Street was as a registered broker, a position he held for a mere six days.

5. The Marriages

For all his success in the boardroom, Donald Trump’s life in the bedroom has been messy at best. The real estate magnate married his first wife, Ivana, in 1977, but things got rocky after Trump’s affair with actress Marla Maples surfaced in New York City tabloids. In 1992, Trump left her with a reported $25 million settlement and married his mistress one year later. His marriage to Maples was even shorter-lived, and the couple divorced in 1999. These days, Trump’s married to Slovenian supermodel Melania Knauss. Together in marital bliss since 2005, this relationship’s proving the third time really is a charm — so far anyway.

4. The Hair

Trump isn’t fooling anyone with that hairdo. That’s not his real hairline; he just blow-dried it forward and then combed it backward. Surprisingly, his hair started out kind of normal in the 1980s. It appeared to be hair sprayed into a pouf, but that was to be expected in the decade in which everything went big. But as the real estate mogul aged, he tried to will himself younger with his hair. It got blonder and blonder until it went yellow. Then it turned into — well, whatever it is that it is now.

3. The Bankruptcies

"I don’t like the B word,” Donald Trump said in 2010 while testifying in a New Jersey bankruptcy courtroom about his gambling company, Trump Entertainment Resorts Inc., which had filed for bankruptcy for the third time. Given the number of times Trump has flirted with bankruptcy, you’d think he’d be used to that word by now.

In 1990, the banking institutions that backed his real estate investments had to bail him out with a $65 million "rescue package” that contained new loans and credit. But it wasn’t enough, and nine months later the famous developer was nearly $4 billion in debt. He didn’t declare personal bankruptcy, although his famous Taj Mahal casino in Atlantic City, N.J., did have to file for it (bondholders ended up taking a 50% stake in the investment). Trump’s economic troubles continued through the early ‘90s, while he was personally leveraged to nearly $1 billion. In 2004, Trump Hotels & Casino Resorts also filed for bankruptcy. The company was only a small portion of Trump’s real estate empire,

but he did still have to personally cough up $72 million to keep it afloat. In 2009, the same company (by then renamed Trump Entertainment Resorts Inc.) filed for bankruptcy again. Yet during all of this, no one ever told Trump, "You’re fired!” Probably because no one could.

2. Trump Vodka

Trump vodka (labelled super premium, naturally) was introduced in 2006 to much fanfare. Under the slogan "Success Distilled,” the liquor was touted as the "epitome of vodka” that would "demand the same respect and inspire the same awe as the international legacy and brand of Donald Trump himself.” At the time, Trump predicted the T&T (Trump and Tonic) would become the most requested drink in America, surpassed only by the Trump Martini. On Larry King Live, he said he got into the vodka business to outdo his friends at Grey Goose. Six years later, Grey Goose is still on top shelves throughout the country. The New York City blog Gothamist reports the vodka has stopped production "because the company failed to meet the threshold requirements.”

Trump Airlines

In October 1988, Donald Trump threw his wallet into the airline business by purchasing Eastern Air Shuttle, a service that for 27 years had run hourly flights between Boston, New York City and Washington, D.C. For roughly $365 million, Trump got a fleet of 17 Boeing 727s, landing facilities in each of the three cities and the right to paint his name on an airplane. Trump pushed to give the airline the Trump touch, making the previously no-muss, no-fuss shuttle service into a luxury experience. But his gamble was a bust. A lack of increased interest from customers (who favoured the airline for its convenience not its fancy new look) combined with high pre–Gulf War fuel prices meant the shuttle never turned a profit. The high debt forced Trump to default on his loans, and ownership of the company was turned over to creditors. The Trump Shuttle ceased to exist in 1992 when it was merged into a new corporation, Shuttle Inc.

Ends