Phil Garber
15 min readDec 2, 2023


Photo by Sam Hojati on Unsplash

Trump, the Grifter, Yesterday, Today and Always

Trump has always been a snake oil salesman, a grifter and cheater and it’s a good time for a brief rundown on trump’s many colossal failures from steak and vodka to yachts and jets. Not surprisingly, trump has used the same tactics, insinuations and lies to avoid the many lawsuits filed against him and his bogus products.

Trump Shuttle Inc.

Trump met the Eastern Airlines president at a party in 1989, and later bought the company for $365 million and created Trump Shuttle Inc. The company lasted all of three years.

In 1990, the U.S. invaded Kuwait and oil prices skyrocketed pushing the U.S. to the brink of a recession. By mid-1990, trump’s airline had lost $18 million. He fired 100 employees and decided to sell and the majority stakeholder, Citigroup, negotiated a sale with US Air.

In October 1988, Eastern Air Lines filed for Chapter 11 bankruptcy protection. Many passengers switched to the competing Pan Am Shuttle, while the previously profitable Eastern Shuttle began bleeding money. Eastern president Frank Lorenzo met trump at the party, and subsequently negotiated the sale for $365 million, more than the projected cost to start up a similar airline, but justifiable if the airline achieved a high market share.

Trump owned Trump Shuttle, Inc. from 1989 to 1992. The shuttle had previously been a “no-frills” operation for business travelers, but true to form, Trump announced that he would convert it to a luxury airline, at a cost of $1 million to remodel each jet.

The new Trump Shuttle aircraft were painted in white livery and the interiors redecorated with such garish features as maple wood veneer, chrome seat belt latches, and gold colored lavatory fixtures. Flights offered free meals, including chicken and steak on some flights, as well as complimentary champagne, beer and wine. Trump Am spent millions on advertising campaigns in an attempt to maintain a strong competitive position.

Trump Shuttle was never profitable. While costs of running the airline rose, many of the corporate customers using the shuttle were cutting travel budgets. At the same time, Trump’s casino business was having serious difficulties, and Trump was forced to surrender control over several business holdings to his bankers in June 1990 to avoid personal bankruptcy. The airline ran out of cash and defaulted on its debt in September 1990.

Trump had personally guaranteed $135 million of the shuttle’s debt. Following the default, Citibank made arrangements for Northwest Airlines to take control of the shuttle in exchange for relieving Trump’s personal liability on its debt, and all sides were reportedly close to an agreement by April 1991. Delta Air Lines agreed to buy the competing Pan Am Shuttle in July, and Northwest announced that its acquisition of the Trump Shuttle was cancelled in August, because the Trump Shuttle’s unions were demanding parity with Northwest employees and Trump refused to discount the price to reflect the added costs.

USAir ultimately reached an agreement in December 1991 to take operational control of Trump Shuttle for up to 10 years. Trump was relieved of at least $100 million of his guarantee, and possibly as much as $110 million, leaving him owing between $25 million and $35 million in the closing out of his ownership of the company.

Trump Mortgage

Trump launched his own mortgage company in 2006 and his son predicted that it would be the №1 home-loan lender in the U.S. A year and a half later, the company shut down amid the housing market crash of 2007.

E.J. Ridings, the company’s president and chief executive officer, first suggested the idea of a new mortgage company to an acquaintance, who happened to be Trump’s son, Donald Jr. As of September 2006, Trump Mortgage was licensed in 25 states and the company claimed that it was the fastest-growing commercial and residential mortgage company in the United States.

The company shut down on August 5, 2007, a result of a poor economy and Ridings’ exaggeration of his credentials. It was reported that Ridings claimed that he was “a top professional at one of Wall Street’s most prestigious investment banks,” but, in fact, he had worked at Morgan Stanley for only three months, and had worked at Dean Witter Reynolds for six days as a stockbroker. Experts also believed that the company expanded too quickly.

“Not only will we make money, but it is a humanitarian venture as well. We have created a safe haven where people can get the best deal on a residential or commercial mortgage without worrying about all the hidden clauses,” Ridings said.

Around $25 million in loans was arranged in February 2006, primarily in New York. As of March 2006, the brokerage was licensed in several states, with nationwide licensing expected in the next few months. Within the first six months of its operation, six top executives left the company.

Jennifer McGovern, a former employee of Trump Mortgage, brokered a $26,500,000 financing, which earned more than $500,000 in commissions for Trump Mortgage. Trump Mortgage collected its commission, but McGovern got nothing. She sued and in 2009, McGovern obtained a judgment of $298,274 against Trump Mortgage. As of March 2016, the judgment remained unsatisfied. The Treasury Department placed a lien on Trump Mortgage in 2009 for $3,555 in unpaid taxes.[

Trump Steaks

Trump launched his name-brand steaks in 2007 specifically for The Sharper Image, a high end catalogue business selling gadgets, electronics and more. Trump Steaks failed to sell well through The Sharper Image, which discontinued sales of the product line after two months.

Prices ranged from $199 for a pack of 12 steak burgers and four steaks, up to $999 for a selection of 16 top cuts.

The Trump Steakhouse in Las Vegas was briefly shut down after it was hit with 51 health code violations, including using expired yogurt and five-month old duck.

As of April 2016 the only place the steaks can still be purchased is at Trump properties.

Trump Vodka

Trump joined the “super premium” vodka industry around 2006. He said the “Trump & Tonic” would become the most popular drunk cocktail in the U.S. By 2011 the drink was no longer being produced under the Trump trademark because the company failed to meet the required threshold for distribution.

In 2007, the distributor, Drinks Americas, signed a deal to export 50,000 cases of Trump Vodka annually to Russia.

Drinks Americas had problems producing the vodka because the glass used in the bottles and the gold leaf labels were expensive and the company could not afford to produce them in large numbers. Trump did not include Trump Vodka among his assets submitted to the Federal Election Committee for his 2016 presidential campaign.

Drinks Americas was subject to several lawsuits surrounding Trump Vodka. Bruni Glass sued over unpaid bills and, as a result, melted in a furnace 500,000 Trump Vodka mini-bottles ready for shipment. Trump also sued Drinks Americas for unpaid royalties, but the case was dismissed for lack of jurisdiction.

In 2011,Trump’s name-brand vodkas were being sold in Israel without authorization. Trump Vodka was relatively popular in Israel because it was made from potatoes and not grain, thus satisfying kosher for Passover dietary laws. However, some Trump Vodka produced in 2013 was found to contain leavened ingredients, making it unsuitable for consumption during Passover.

Trump: The Game

Trump issued his own pseudo-Monopoly board game in 1989, but after poor sales, it was discontinued after a year. Parker Brothers re-released Trump: The Game in 2004 following the success of Trump’s reality television series, The Apprentice, from earlier that year. Partly because Trump: The Game had a rule book of more than 12 pages, it received poor reviews from critics and the public audience.

Jeffrey Breslow, who pitched the idea of the game to trump, did not believe that the game would become as popular as Monopoly, and 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 2011, Time magazine listed the game among the “Top 10 Donald Trump Failures,” referring to it as one of Trump’s “ridiculous ideas.”

In May 1991, Trump was sued 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. Trump provided no records to prove his claim about charity donations. The lawsuit was dismissed.

Trump Ice

Trump Ice, promoted as the “purest” bottled water, was shut down in 2010.

Trump Ice was initially sold only at Trump-owned facilities but in 2003, distribution branched out to other national grocery chains and specialty food stores. Kelly Perdew, the winner of The Apprentice 2, was executive vice president while trump personally invested $498,000 in Trump Ice.

“Trump Natural Spring Water” is still listed as exclusively available at Trump-branded hotels, restaurants and golf clubs on Trump’s website .

Entertainment Weekly rejected the brand’s claim that Trump Ice is “one of the highest quality spring waters in the world with an optimum mineral content” by pointing out its “very low” mineral content, plus the fact that it is bottled in plastic, and not glass. A CNN review of Trump products argued that Trump Ice “is clearly not about the water but rather a vehicle for the Trump image.” was a search engine for bargains on luxury travel deals. Powered by, the site launched in 2006 and closed down a year later.

Trump had claimed the company was “working with an esteemed group of partners including Travelocity, American Airlines, American Express, Blue Star Jets and Joonbug.” The site featured 60,000 hotels, including “Trump’s picks,” which were marketed as trump’s favorite hotels and resorts.

Henry Harteveldt, a travel industry analyst with Forrester Research and the former marketing director for Trump Shuttle, called GoTrump a “vanity site” for Trump and said it would not make much money. In March 2016, “” redirected to, which was the official website of Trump’s presidential campaign. By 2022, the url was purchased by The Lincoln Project , an anti-trump political action committee.

Trump Magazine

The Trump Magazine was a collaboration between the Trump brand and a company called Niche Media. It launched in 2007 and two years later, the magazine was nowhere to be found, a victim of poor circulation and the recession.

According to a press release, the quarterly magazine saw early success, “cashing in on the booming advertising market for yachts and other high-end commodities.” But 2007 to 2009 was probably a difficult time for the “booming advertising market for yachts.”

The magazine was the latest iteration in a series of trump publications that focused on trump’s lifestyle and personality. Trump was on the cover of the spring issue while trump’s daughter, Ivanka, graced the summer cover to help attract male readers. Niche Media bought Trump Magazine in 2007 but ceased publication in May 2009, because of low advertisement sales. In February 2016, the New York Daily News reported that issues of Trump World “are nowhere to be found online and hardcopies are likely a rare collector’s item.”

New Jersey Generals

The United States Football League (USFL) was created in 1983. A year later trump bought the New Jersey Generals of the fledgling league. In 1985, the team and the league, folded.

Trump bought the Generals to use as a vehicle to get an NFL team. His plan was to move the Generals across the Hudson River to New York, and play at Shea Stadium until the construction of a new 80,000-seat “Trump Stadium” in Manhattan. The team never joined the NFL and “Trump Stadium” remained another trump pipe dream.

Jeff Pearlman, author of the 2018 book, “Football For A Buck: The Crazy Rise and Crazier Demise of the USFL” wrote that the league “died beneath the weight of a particularly egotistical and bombastic team owner―a New York businessman named Donald J. Trump.”

In a May 29, 2014 story in the Los Angeles Times, reporter Chris Dufresne wrote, “Let the record show that Trump, three decades ago, not only killed off the New Jersey Generals of the United States Football League but also killed off the entire USFL. Many fine people lost jobs because of Trump’s audacious, predatory and unnecessary business practices.”

Dufresne wrote that trump bought the Generals “with the hope he could ruin the USFL and then force a merger with the NFL,” which he hoped would absorb the Generals in the process. Under trump’s direction, players’ salaries went through the roof, causing huge strains on the teams in the league. In response, trump encouraged the league to take on the NFL. When USFL franchises started to fail under the financial strain caused by trump, he helped convince USFL owners to sue the NFL under federal antitrust laws. Trump claimed the USFL “won” its antitrust lawsuit against the NFL. The dying league was awarded a whopping $3, not exactly a major victory. The USFL did not compete head on with the NFL and trump never carried through on another plan to buy the Buffalo Bills.

“Trump can spin history any way he wants,” Dufresne wrote. “He can massage it and sugarcoat it — even turn a blind eye to it. But he can’t rewrite it because there are still too many eyewitnesses.”

Trump Entertainment Resorts Inc.

Trump Entertainment Resorts, Inc. was a gambling and hospitality company founded in 1995 by trump. The company previously owned and operated the now-demolished Trump Plaza and Trump World’s Fair (both in Atlantic City), the now-closed Trump Marina, Trump Casino & Hotel in Gary, Ind., Trump 29 in Coachella, Calif., and Trump Taj Mahal in Atlantic City. The company filed for bankruptcy in 2004, 2009 and 2014. It became a subsidiary of Icahn Enterprises in 2016. Since then, all of the company’s properties have been closed and sold.

In 1995, Trump established Trump Hotels and Casino Resorts (THCR) as a publicly traded company, granting it ownership of the Trump Plaza and the under-development Trump Casino in Gary, Ind. The following year, THCR bought the Trump Taj Mahal at a valuation of $890 million, and bought the Trump Castle from Trump for $486 million (including $355 million in assumed debt).

In 1997, THCR was one of 11 applicants for three casino licenses in Detroit, Mich., with a $542-million proposal for the Trump Motor City Hotel Casino, in partnership with former professional football player, Mel Farr. The bid was ultimately dropped from consideration because of Mayor Dennis Archer’s doubts about the company’s financial condition.

In 1999, THCR agreed to purchase the Flamingo Hilton Casino Kansas City for $15 million, but the deal fell through when Missouri gaming regulators did not approve the company’s gaming license by a contractual deadline. THCR entered a management agreement in 2000 to operate the Spotlight 29 Casino, an Indian casino in Coachella.

On October 10, 2016, the Trump Taj Mahal, the company’s last operating property, closed for the final time.

Trump Plaza remained vacant after the company had gone defunct and its assets were acquired by billionaire investor Carl Icahn. Icahn wanted to demolish the casino, but was unsuccessful in seeking $5.6 million in tax funds to pay for the demolition. The tax funds were not approved and the building remained standing. In March 2020, the city declared the building uninhabitable and demolition began that summer. The building finally imploded on Feb. 17, 2021.

After his election as president, trump named Icahn a special advisor on regulatory reform.

Trump University

Trump University, also known as Trump Wealth Institute and Trump Entrepreneur Initiative LLC, opened in 2005, as a real estate training program. For six years, the for-profit, non-accredited school charged its students $35,000 for tuition. That year, trump licensed his name to an affiliate program called the Trump Institute. The “university” closed in 2011.

The “university” conducted three- and five-day seminars often called “retreats” and used high-pressure tactics to sell them to its customers. Students received no college credits, no degrees, no grades.

“I went to the Wharton School of Finance … I have a great feeling for education and for knowledge and learning … I love the idea of helping people, because I’ve had a lot of experience with real estate, to put it mildly,” trump said.

In 2010, four students sued the “university” for “offering classes that amounted to extended ‘infomercials,’ ‘selling non-accredited products,’ and ‘taking advantage of these troubled economic times to prey on consumer’s fears.’”

In 2013, New York Attorney General Eric Schneiderman sued Trump and Trump University for allegedly defrauding students.

An article in the National Review called the organization a “massive scam.”

In March 2010, N.Y. Deputy Commissioner for Higher Education Joseph Frey notified Trump that “Use of the word ‘university’ by your corporation is misleading and violates New York Education Law and the Rules of the Board of Regents.” In June 2010, Trump University changed its name to “The Trump Entrepreneur Initiative.”

On Aug. 24, 2013, the State of New York filed a $40 million civil suit against Trump University alleging illegal business practices and false claims made by the company. New York Attorney General Eric Schneiderman described Trump University as a bait-and-switch scheme and accused trump of misleading more than 5,000 people to pay up to $35,000 to learn his real estate investment techniques.

Trump denied the allegations and said Schneiderman was “a political hack looking to get publicity.” Trump filed a complaint alleging that Scheiderman’s investigation was accompanied by a campaign donation shakedown. A New York ethics board investigated the complaint and dismissed it in August 2015.

In October 2014, a New York judge found Trump personally liable for operating the company without the required business license.

In May 2010, the consumer protection division of the state of Texas found the company was “engaging in false, misleading and deceptive practices” and had defrauded Texas taxpayers out of $2.6 million. According to John Owens, the Texas attorney general’s deputy chief of consumer protection, an estimated 267 Texans spent more than $425,000 on the three-day seminars, and 39 purchased Trump’s “Gold Elite” package of additional classes and other perks costing $35,000 each. Another 150 customers from Texas spent more than $826,000 on other goods and services.

The Texas consumer protection division under then Attorney General Greg Abbott announced plans to file a lawsuit to recover more than $2.6 million that Texas taxpayers who had been students at the “university” had “spent on seminars and materials, plus another $2.8 million in penalties and fees.” The investigation was dropped and no lawsuit was filed, but Trump University agreed to cease operations in Texas. Abbot has since been elected governor and Owens claimed that decision “not to sue [Trump] was political.” Trump later donated $35,000 to Abbott’s campaign for governor.

David S. Morales, the Deputy Attorney General in 2010, admitted in 2016 that he had quashed the $5.4 million suit without discussing the issue with Abbott. In 2018, Trump nominated Morales to serve as a judge at the District Court for the Southern District of Texas.

On Oct. 18, 2013, California businessman Art Cohen filed a class action suit on behalf of consumers throughout the United States who purchased services known as “Live Events” from Trump University after Jan. 1, 2007. It alleged the events were essentially a scheme to defraud and accused trump of misrepresenting Trump University “to make tens of millions of dollars” while actually delivering “neither Donald Trump nor a university.” The suit named Trump as the sole defendant and sought restitution as well as damages, including punitive and treble damages.

U.S. District Court Judge Gonzalo Paul Curiel certified the suit and trump’s lawyer, Alan Garten, said the judge should recuse himself because of his “animosity toward Mr. Trump and his views.” Curiel remained the judge for the case and set a trial date of Nov. 28, 2016.

During presidential primary campaign speeches, trump repeatedly called the judge a “hater” and described him as “Spanish” or “Mexican” though Curiel was born in Indiana to parents who had immigrated to the U.S. from Mexico.

Trump agreed on Nov. 18, 2016, to pay $25 million to settle the class actions and the New York suit. Under the settlement, Trump who had previously vowed he would never settle, did not admit any wrongdoing. The settlement was paid not by trump but by his friend and Las Vegas hotel business partner, billionaire Phil Ruffin. Ruffin admitted to paying Trump $28 million in 2018, but claimed it was for “back-fees” related to Trump International Hotel Las Vegas and unrelated to the Trump University case.

Ruffin is a longtime friend and business partner of trump. Trump flew on Ruffin’s private jet to Moscow in 2013 for the Trump-owned Miss Universe Pageant. At the time Ruffin was married to a former Miss Universe, Ukrainian supermodel, Oleksandra Nikolayenko. According to the so-called Steele dossier, during the trip, trump allegedly met with prostitutes at a hotel room where they practiced urolagnia, a sexual deviation involving urine otherwise called a “Golden Shower.”

Former British intelligence officer, Christopher Steele reported the alleged activities, although they have not been substantiated in any major media outlets. Trump has repeatedly denied having stayed overnight in Moscow for the pageant despite flight records indicating that Ruffin’s plane arrived in Moscow on a Friday morning and departed Sunday. On that same trip, Ruffin was reported to have attended a meeting with trump, trump’s bodyguard Keith Schiller, and local Russian officials regarding the development of a Trump Tower Moscow.

In 2015, Ruffin gave $1 million to the Make America Great Again PAC, a super PAC supporting trump’s campaign for the presidency. The super PAC shut down and refunded Ruffin’s money after the Washington Post reported on its close association with Trump’s campaign. At an event in January 2016, Trump praised Ruffin for making a $1 million donation to veterans’ groups.

Together with his spouse, Ruffin contributed a total of $1.5 million to trump’s 2020 presidential campaign.

In 2010, the office of Texas Attorney General Greg Abbott investigated Trump University. No suit was brought, but Trump University closed its operations in Texas.



Phil Garber

Journalist for 40 years and now a creative writer