Iconic Tour

Learning from Donald Trump's biggest business wins

Tim Mullaney, special to CNBC.com
Donald Trump, president and chief executive of Trump Organization Inc. and 2016 Republican presidential candidate, acknowledges cheering audience members before speaking at a campaign rally at the Myrtle Beach Sports Center in Myrtle Beach, South Carolina, U.S., on Friday, Feb. 19, 2016.
Luke Sharrett | Bloomberg | Getty Images

Donald Trump's presidential campaign is built on a carefully burnished image of success — but how real is it?

Real enough that he claims to be worth $10 billion or more, though independent estimates are lower, including Bloomberg News' estimate of $2.9 billion last year and Forbes' estimate of a net worth of $4.5 billion. But a billionaire is a billionaire. We'd all rather be in the fight as to whether our wealth was $2.9 billion or $4.5 billion or $10 billion, right?

Yes, Trump is a beneficiary of inheritance, huge early success and has taken companies into bankruptcy, something he said is a function of how all corporations use existing laws, won't apologize for and has only happened "four times out of hundreds."

For all the criticism Trump receives about his business prowess, he has had many successful ventures during his long career. Sorry, haters: It's not just decades of blustery self-preservation. Here are some of Trump's biggest business wins.

By Tim Mullaney, special to CNBC.com
Posted 19 March 2016

The Grand Hyatt

The Grand Hyatt Hotel in New York City.
Brian Godfrey | CNBC

It all begins with real estate, and the Hyatt was Trump's first big signature deal as a Manhattan developer, though some say help was needed. His father was a close friend of then-New York mayor Abe Beame, and Trump won a 40-year abatement on property taxes in exchange for redeveloping a derelict hotel adjacent to the city's historic Grand Central train station. In addition, Trump convinced the Hyatt chain to guarantee half of the $70 million construction cost, since the then-27-year-old developer couldn't get such a big loan on his own. Trump's father guaranteed the other half.

The Los Angeles Times described the deal as "one of the most profitable marriages in the hotel and real estate business" back in 1994, though at the time, Hyatt was suing Trump for refusing to pitch in for a renovation project (not the only lawsuit between the two parties).

The LA Times reported in 2011 that the deal cost the city $60 million in foregone taxes in its first decade. The Trump Organization says the city made the deal because so many surrounding buildings were in or on the verge of foreclosure. Trump has argued that the project was so crucial to New York's redevelopment that the city got a good deal, too. On October 7, 1996, the Pritzker family of Hyatt fame purchased Trump's half share in the hotel for $142 million.

Trump Tower

Trump Tower in New York City.
Mattia Panciroli | Flickr CC

If the Grand Hyatt made Trump rich (beyond family money), Trump Tower made him famous. The 68-story building opened in 1983. It's rated the 17th-best condo building in Manhattan today by CityRealty.com, and the fifth-best in Midtown, with one-bedroom apartments selling recently for about $2.5 million.

When it opened, Trump Tower quickly became a part of the city's imagination. Located on Fifth Avenue between 56th and 57th streets, it attracted residents as diverse as actor Bruce Willis and former Haitian dictator Jean-Claude (Baby Doc) Duvalier. The first 26 floors hold office and commercial spaces, according to the Trump Organization.

Trump has used the property to promote his brand, featuring it in "The Apprentice" and launching his presidential campaign there. He lives in the penthouse, said to be decorated to resemble the interior of the Palace of Versailles in France.

The books

Republican presidential candidate Donald Trump holds up his book 'The Art of the Deal'.
Eric Schultz | AP

The famous Trump brand has gotten a boost from sales of his books, beginning with 1987's "The Art of the Deal." Trump has claimed the book sold 1 million copies and is the best-selling business book of all time. His latter claim isn't true: "In Search of Excellence," by Tom Peters and Roger Waterman, for example, sold 3 million.

Pulitzer Prize-winner PolitiFact reported last year that available data can't settle whether the book sold 1 million copies, but it was on The New York Times best-seller list for 51 weeks. Trump's website says all of his "personally written" books have made the list.

Trump has written or co-written 20 books, from "Surviving at the Top"" to "How to Get Rich." In nods to his recent interests, one is about lessons he learned doing "The Apprentice" and "Celebrity Apprentice" for NBCUniversal, and another is a 2005 book of golf tips. His newest book, "Crippled America: How to Make America Great Again," was released last year to coincide with his campaign — one reviewer noted its "About the Author" section runs 14 pages.

"Crippled America" ranks 347th among books in sales at Amazon.com, as of March 18, and in the top 10 on Amazon among political titles, specifically. Yahoo Finance reported that it sold 199,000 copies in its first four months on the market, citing Nielsen BookScan data that covers about 85 percent of the market.

"The Apprentice"

Donald Trump attends the 'Celebrity Apprentice' Red Carpet Event at Trump Tower on January 5, 2015, in New York City.
Mike Pont | FilmMagic | Getty Images

"The Apprentice" debuted on NBC in 2004 and drew 28 million viewers for its first-season finale. The show lasted for six years before switching to its "Celebrity Apprentice" format, which ran until 2015, interrupted by a resurrection of the original format that lasted one season. In its last season, "Celebrity Apprentice" drew an average of 7.6 million viewers, slightly less than "Shark Tank" on ABC and 67th of 188 network shows that season. NBC Universal plans to bring the show back, featuring Arnold Schwarzenegger as the host.

Trump has said he made $213.6 million from the 14 seasons of "The Apprentice," a claim other sources have disputed. The show played a role in President Barack Obama's famous in-person trolling of Trump at a White House Correspondents' Association dinner, teasing Trump that the president would be kept awake nights trying to decide which celebrity to fire for on-air missteps. Trump wasn't amused, and as Obama spoke, the president had a very different kind of assault on his daily planner: Final preparations for the next day's raid to kill al-Qaeda leader Osama bin Laden were under way.

40 Wall Street

The Trump Building at 40 Wall Street in New York.
Jin Lee | Bloomberg | Getty Images

Trump has done much less real-estate development since the early 1990s, but of his more recent New York deals, 40 Wall Street stands out as a success.

Trump said he paid about $1 million for the 72-story building, which once was the tallest in the world, but other reports claim it was more like $10 million. According to PropertyShark.com, the building is now worth $145 million. Trump won praise from market pros for aggressively cutting prices to refill the tower as a raft of lease expirations hit in the wake of the last recession.

Trump Golf

Donald Trump plays a round of golf after the opening of The Trump International Golf Links Course in Balmedie, Scotland.
Getty Images

Trump has built an elite group of 17 golf courses, either owned by him or using the Trump name under license, focusing on buying financially distressed courses and renovating them. His 2015 financial disclosures put the value of his golf-related businesses at $550 million to more than $675 million. He valued nine of his courses at $50 million or more each, a price no U.S. golf course sold in 2013 commanded.

Trump's golf courses are beginning to command an impressive list of top-tier tournaments. He interrupted his campaign to visit the final round of the World Golf Championships-Cadillac Championship Open at his Miami Doral resort this month. Next year's U.S. Women's Open will be played at his Bedminster, New Jersey, club, where the going rate for rarely available non-member foursomes is $1,800.

The campaign

Republican presidential candidate Donald Trump speaks at a rally on March 13, 2016 in Boca Raton, Florida. Primary voters head to the polls on March 15th in Florida.
Rhona Wise | AFP | Getty Images

For a long-time, Trump said he was self-funding his campaign, but when it was revealed last October that a vast majority of the money his campaign spent didn't come from his own coffers but donations, it was also a sign of how successful a sales organization you could call the Trump presidential run. Individual donations of, on average, $50 had raised as much as $3.7 million during the summer of 2015, when Trump rose to the top of the polls, according to an October 2015 New York Times report. Earlier in the campaign, Trump has provided $1.9 million, the bulk of the funding.

In February, the Times reported that Trump was closing in on one of his boasts: to become the first person to turn a profit while running for president. Based on filings with the Federal Election Commission, more than half of Trump's campaign spending came from supporters' checks, and he spent just $12.4 million in 2015, millions less than rivals. In addition, more than $2.7 million was paid to at least seven companies Trump owns or to people who work for his empire, including $2 million for flights on his own planes and helicopters and $250,000 to his Fifth Avenue office tower.

The Times argued that money Trump has lent to the campaign could ultimately be paid back to him through merchandise sales, like the "Make America Great Again" hats. Meanwhile, Trump has generated $1.9 billion of news coverage, dwarfing the estimated value of news coverage given to any other candidate, according to an analysis conducted by the Times' "Upshot" section in conjunction with mediaQuant, all while spending less on advertising than any presidential rival.

While Trump advisors have stressed he is not running for president to make money, and critics have harped on these numbers to show his campaign isn't self-funded, it's not so hard to make a case that Trump 2016 has been one of Trump's most successful business endeavors.

The name

Presidential hopeful Donald Trump speaks during a rally March 14, 2016 in Vienna Center, Ohio.
Brendan Smialowski | AFP | Getty Images

Like him or not, Trump's really, really rich. Forbes' estimate of $4.5 billion is good enough for the 121st place among Americans to make the Forbes 400, and 324th place among all of the world's billionaires.

While Drumpf got a big spike in late February and early March, thanks to HBO's John Oliver — who explained the Trump family's history pre-U.S. days — it can't keep pace with its Americanized self, which has soared again in search results while Drumpf has sputtered. (Though Oliver's "Last Week Tonight" website did sell out of Drumpf hats.

Trump's come a long way from the dark days of the early 1990s, when he flirted with insolvency and in a now oft-cited anecdote from "The Art of the Comeback" wrote that while walking down the street with Marla Maples (Trump's second ex-wife), they passed a beggar on Fifth Avenue and Trump told Maples the beggar was worth $900 million more than Trump was. "I'm worth minus $900 million," Trump said. At the time, Trump lacked the cash to make his loan payments.

There's really no business that's been better for The Donald than the Trump brand name. But now there's some question as to whether the presidential ambitions, while providing Trump with the stature he craves, are doing damage to the luxury brand he has built over decades.

A longtime survey of luxury brand reputation found in December 2015 that the reputation of the Trump brand had declined and "has lost the confidence of the people who can afford to stay at one of his hotels, play at one of his country clubs or purchase a home in one of his developments," according to a Politico Magazine report on the survey, which was conducted by the BAV Consulting division of Young & Rubicam. "It is also rapidly losing its association with the gilded traits Trump has long promoted as the essence of his business," the report said.