Donald Trump's biggest business hits and misses

Hit: Trump International Hotel and Tower

Trump bought the former Chicago Sun-Times building in late 2004 for $73 million and turned the newspaper's seven-story building into a 98-story hotel and condo. Trump originally wanted it to be the tallest building in the world, but after the attacks on Sept. 11, 2001, he scaled the project down. When it opened in 2009, it became the fourth-tallest building in the United States.

Miss: Trump Vodka

With the launch of Trump Vodka, the billionaire said "By the summer of [2006], I fully expect the most called for cocktail in America to be the T&T or the Trump and Tonic." The vodka was discontinued in 2011, according to The Wall Street Journal, with the only remaining way to get your hands on a bottle through eBay.

Hit: Trump Winery

Formerly Kluge Vineyard and Estate, Trump Winery is located on Trump Vineyard Estates in Charlottesville, Virginia. It was purchased in April 2011 and officially opened later that year. The business is now owned by Trump's son Eric, and numerous bottles of the company's wine have won accolades over the years.

Miss: Plaza Hotel

"I haven't purchased a building, I have purchased a masterpiece - the Mona Lisa," Trump said after buying the famous Plaza Hotel in New York City in 1988. Trump won a bidding contest between other Manhattan developers for the hotel and borrowed money to pay nearly $400 million for the property. Despite filling rooms and charging more for them, the Plaza wasn't able to cover its interest payments to banks. The ownership lasted until 1995 when the hotel was sold to foreign investors, and none of the money from the deal went to Trump but instead to the banks that lent him money.

Hit: Mar-a-Lago

Trump bought the 1920s estate in Palm Beach, Fla. in December 1985 for less than $8 million, before renovating the 58-bedroom, 33-bathroom facility to include a new 20,000-square-foot ballroom. After being acquired by Trump, the Mar-a-Lago Club played host to large-scale events, including the International Red Cross Ball, musicians -- Billy Joel and Celine Dion have both performed concerts there -- and vacationing celebrities, including Michael Jackson, Sean Combs and Jennifer Lopez. After taking office as the 45th president of the United States, Trump spent several weekends at Mar-a-Lago, referring to the estate as the "Winter White House," and even played host to world leaders, including Japanese Prime Minister Shinzo Abe.

Miss: Trump Steaks

Exclusively introduced at the consumer electronics chain The Sharper Image, Trump Steaks, or "The World's Greatest Steaks," launched in June 2007 to much public relations fanfare, with the billionaire and his beef featured on the cover of The Sharper Image's catalog. Prices for the cuts ranged from $199 for a pack of 12 steak burgers and four steaks all the way up to $999 for the "Connoisseur Collection" of 16 cuts. The steaks were short-lived, with Sharper Image selling them for only two months in 2007. Check out the original ad for the steaks here: https://youtu.be/LyONt_ZH_aw

Miss: Trump Airlines

Originally Eastern Air Shuttle, Donald Trump bought the airline in 1988 for $365 million. He aimed to make the flights into a luxury experience by adding chrome seat-belt latches, gold-colored bathroom fixtures and more decadent styling. But a lack of interest from customers and pre-Gulf War fuel prices led to zero profit and led Trump to cede control to creditors. The airline ceased to exist when it merged with Shuttle Inc. in 1992.

Hit: Grand Hyatt New York

The deal that put him on the map, Trump bought the former Commodore Hotel in 1977, and after six years of construction and $100 million in upgrades, the Grand Hyatt New York opened. The 26-story hotel is in the heart of Manhattan, and the deal was made with help from his father, Fred Trump, who worked with former New York Mayor Abe Beame to get a $400 million property tax abatement for the project. In 1996, Trump sold his half interest in the hotel to the Hyatt Corporation for $140 million.

Miss: Trump University

Trump University operated from 2005 to 2011 and focused on Web-based seminars and courses in real estate, asset management and entrepreneurship. The program has since been the subject of accusations of fraud by New York State, with former students alleging Trump and his school of misleading advertising to dupe 5,000 people to pay up to $35,000 for seminars through the unlicensed, unaccredited "university." Shortly after being elected president, Trump agreed to pay $25 million to settle class-action lawsuits that accused the now-defunct Trump University of defrauding students.

Miss: Trump on the Ocean

Trump on the Ocean was abandoned due to extensive damage from superstorm Sandy. Trump had planned a 38,560-square-foot catering facility at the Central Mall boardwalk at Jones Beach. The plan was ultimately killed in December 2012 by Trump and state officials.

Miss: Trump Entertainment Resorts Inc.

Trump Entertainment Resorts owns the Trump Taj Mahal in Atlantic City, which filed for bankruptcy four times, and used to own Trump Plaza, Trump Marina and other since-sold resorts. Despite the four bankruptcies and sold assets, the company still exists -- although without Trump, who originally founded the company in 1995 but is no longer involved after new parent company Icahn Enterprises assumed full control in February 2016.

Hit: Wollman Rink

After more than six years of inactivity and rising costs, Donald Trump persuaded then New York City Mayor Ed Koch in 1986 to let him complete work on Wollman Rink in Central Park in four months at $2.5 million. Initially, Koch objected to Trump's stipulation that he would pay for the renovations himself in exchange for being allowed to run the venue and an adjacent restaurant to recoup costs, according to Forbes. After public pressure mounted, Koch caved, and the rink reopened in November 1986 with the total costs of renovations coming in under budget at $2.25 million.

Miss: GoTrump.com

A search engine for bargains on luxury travel deals, GoTrump.com was powered by Travelocity and launched in 2006. The site promised deals on airfare, hotels and tips on vacation from Donald Trump himself. At the time, Trump told The New York Times "When you get millions of people using your service, and you get X dollars per person, it adds up to a lot of money." The following year, the site shut down.

Miss: The New Jersey Generals

Trump's foray into the world of professional football came in 1984 as the billionaire became owner of the New Jersey Generals, part of the short-lived United States Football League. Trump sold the team and bought them back in the same year with little luck; in 1985, both the Generals and the entire USFL folded. In this March 8, 1984 photo, Trump shakes hands with Herschel Walker after agreement on a four-year contract with the Generals.

Hit: The Trump Building

Originally known as the Bank of Manhattan Trust Building, the skyscraper at 40 Wall Street in Manhattan was bought by Donald Trump in 1995 and immediately renamed The Trump Building. Trump claimed he bought the building for $1 million during The Apprentice's fourth season, but The Wall Street Journal reported that he bought it for $10 million. Nevertheless, the building proved to be a wildly successful investment for the mogul, with estimates that the 72-story property is now worth at least $400 million.

Miss: Trump Mortgage

Trump launched Trump Mortgage in the spring of 2006, telling CNBC "I think it's a great time to start a mortgage company." The company connected lenders to borrowers looking for loans. Promising to be the "strongest and safest residential and commercial mortgage company in the industry," the company ultimately shuttered less than two years after launching.

Hit: Trump Tower

Trump Tower, which serves as the headquarters for The Trump Organization and the primary penthouse condominium of Trump's, opened in November 1983 after four years of construction. The 57th tallest building in New York City, the Trump Tower features Gucci's flagship store and has had notable tenants like Bruce Willis and Andrew Lloyd-Webber. Trump Tower also served as Trump's base of operations for his presidential transition team.

Miss: Trump the Game

Revived with a limited edition in 2005 with "The Apprentice" show-runner's catchphrase "You're Fired!" added into the game, Trump: The Game had a single-year run in the late 1980s when it was discontinued after poor sales. You can purchase the game today from online retailers. Check out the original commercial for the game here: https://youtu.be/OdY31mDsBmU

Miss: The Trump Network

Launched in November 2009 in front of a packed audience at the Hyatt Regency in Miami, The Trump Network was described by Trump as a "new dream" for Americans after many were hit hard in the Great Recession. The business centered around selling nutritional supplements that came from Ideal Health, which was purchased by Trump in 2009. The business was eventually sold in 2012.

Hit: The Apprentice

"The Apprentice" was a breakout hit for NBC and one of the most-watched programs on the channel for about a decade after premiering in 2004. The show wasn't just a ratings hit: According to Trump, he took in $213.6 million for his 13 years of hosting, or more than $1 million per episode. The show also spawned a spinoff with "The Celebrity Apprentice," and in Trump's absence, former California Gov. Arnold Schwarzenegger has been hosting the new season.

Miss: Trump Ice

Available at Trump's casinos for years, Trump Ice is touted as "one of the purest natural spring waters bottled in the world." When asked by New York Magazine about the fiery packaging, Trump said "It is fiery, isn't it? It's fire and ice! The water puts out the fire." Production shut down in 2010.

Hit: Trump Model Management

Trump Model Management, or Trump Models, is a model agency founded by Donald Trump in 1999. Past and present models include Paris Hilton, Isabella Rossellini, Patricia Hartmann and Trump's wife Melania Trump.

Miss: Trump Magazine

Trump Magazine launched in late 2007 as a joint venture between Trump and Ocean Drive Media Group, now Niche Media. The goal was to attract affluent and wealthy readers in major U.S. markets, with the magazine having "early success, cashing in on the booming advertising market for yachts and other high-end commodities," according to a press release at the time. The magazine folded less than two years later in 2009, according to the Daily News.

Miss: Trump Tower Tampa

The Trump Tower Tampa was a planned 52-story project in 2006 that went sour from the economic downturn. Like many Trump buildings, his name was licensed to the developers of the project who ultimately sought bankruptcy protection in 2008. Dozens of condo buyers sued, and a bankruptcy court ruled that the developer Simdag/Robel would repay half of a buyer's down payment. Others who sued Trump directly had their lawsuits settled out of court. A real estate developer purchased the site in 2011 for $5 million.

The Doral Country Club and Doral Golf Resort & Spa saw a handful of different owners since New York City developer Alfred Kaskel purchased and developed the swampland in 1959, with the club mired in debt after the 2008 market crash. Described as the "deal of a lifetime" in Forbes, the resort and courses were purchased in 2011 for the "bargain-basement price" of $150 million by The Trump Organization in a deal spearheaded by Ivanka Trump. The organization owns four of the five courses.