Donald Trump has long promoted himself as a successful businessman, but was he truly a business leader in the traditional sense? While he exhibits some characteristics of a founder, his track record suggests he lacks the operational discipline expected of an effective CEO. Despite branding himself as a master dealmaker, he has seen multiple business ventures fail. Here is a look at some of his most notable business missteps.

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Trump Airlines

In 1988, Trump purchased Eastern Air Shuttle, a no-frills airline operating hourly flights between Boston, New York City, and Washington, DC, for $365 million. He sought to turn it into a luxury airline. However, the airline never turned a profit, and mounting debt led to Trump defaulting on his loans.

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Trump Vodka

In 2006, Trump introduced his own vodka brand with the slogan "Success Distilled." Advertisements for the product claimed it would "demand the same respect and inspire the same awe as the international legacy and brand of Donald Trump himself." Confident in its success, he predicted that the "T&T" (Trump and Tonic) would become the most popular drink in the country. However, production ceased in 2011 due to low demand.

Trump Casinos

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Trump Entertainment Resorts, which operated three Trump-branded casinos in Atlantic City, filed for bankruptcy for the fourth time in 2014. Trump attempted to distance himself from the company, saying that apart from the name, he had "nothing to do with it," despite owning 28% of its stock.

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Trump: The Game

In 1989, Trump launched a Monopoly-style board game, which was pulled off the shelves within a year due to poor sales. He made a second attempt in 2005, releasing an updated version tied to The Apprentice, but this too was discontinued.

Trump Magazine

Trump introduced his own luxury magazine in 2007. However, the publication folded just a year and a half later.

Trump Steaks

In June 2007, Trump launched a premium steak line. Despite his claims that they were the "world’s greatest" steaks, the business failed. The Trump Steakhouse in Las Vegas was also shut down in 2012 after receiving 51 health code violations.

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GoTrump.com

Trump ventured into the travel industry in 2006 with GoTrump.com, a luxury travel search engine powered by Travelocity. However, the website was shut down just a year later.

Trump University

In 2005, Trump launched Trump University, a for-profit, non-accredited institution. In 2010, four students filed a lawsuit against the university, claiming the courses were little more than extended "infomercials." Following the lawsuit, the business rebranded as The Trump Entrepreneur Initiative, but it shut down entirely in 2011.

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Trump Mortgage

In 2006, Trump entered the mortgage business. However, Trump Mortgage collapsed within a year and a half.