life has been about winning. I like to win. I like to close the deal.”24
—Donald J. Trump
Donald Trump’s favorite word may be “win.” Implicit in how he uses “win” is that someone must lose, get defeated, or get beaten. Merriam-Webster defines “win” as “to gain in or as if in battle or contest” or “to gain the victory in a contest.”25
Negotiation has traditionally been viewed as a competitive contest in which you win or lose. Not both. And not win–win.
This is an essential part of Donald Trump’s life. And it permeates his business deals and way of thinking.
Where did it start? It may simply be in his DNA, but this attitude first openly manifested itself at the New York Military Academy, where he was sent at age 13. As noted in Trump Revealed,
Donald’s competitive drive took over as he learned to master the academy. He won medals for neatness and order. He loved competing to win contests for cleanest room, shiniest shoes, and best-made bed. For the first time, he took pride in his grades; he grew angry when a study partner scored higher on a chemistry test, even questioning whether he had cheated.26
He learned much of this from World War II combat veteran and the Academy’s baseball and football coach Theodore Dobias. As Dobias in 2014 told Pulitzer Prize–winning journalist Michael D’Antonio, author of The Truth about Trump, he “taught [his players] that winning wasn’t everything, it was the only thing.”27
This winning “was the only thing” quote from legendary Green Bay Packers’ coach Vince Lombardi greatly impacted Trump. Dobias told D’Antonio, “Donald picked right up on this. He would tell his teammates, ‘We’re out here for a purpose. To win.’…. He would do anything to win…. [Trump] just wanted to be first, in everything, and he wanted people to know he was first.”28
Trump recognized this, believing that “his ball-field experiences were formative because they made him locally famous and because they instilled in him the habit of winning,” according to D’Antonio.29
Trump also became a lifelong sports fan, where “in Trump’s zero-sum world of winners and losers, sports always held a special place.”30 Sports is the quintessential zero-sum environment, where individuals or teams win or lose.
Of course, a win–lose, zero-sum mindset can be positive or negative in negotiations and life. Sometimes both.
For instance, Donald Trump’s dominant win-at-almost-all-costs attitude was reflected in his purchase of the United States Football League’s New Jersey Generals in 1983 and his effort to parlay it into an NFL franchise.
Trump’s Win–Lose Approach to Get into the NFL
Donald Trump bought the USFL’s New Jersey Generals in 1983 with two goals in mind: own a successful NFL team and stadium, and mass market the Trump brand. How did he intend to do this? And how did his win–lose attitude figure into it?
Three elements of his effort illustrate his intentions and win–lose attitude:
Trump needed to win games right away,
Trump needed the USFL to compete with the NFL in the fall, and
Trump’s last shot to win—sue the NFL.
Trump Needed to Win Games Right Away
In 1983, Donald Trump had just opened Trump Tower, a 58-story tower in New York City with his name emblazoned in big gold letters above the entrance. And he was selling Trump Towers condos at a great clip and receiving loads of positive publicity for its design and as the luxury place to live in Manhattan. Trump Tower was a “win” right away.
Next up—he bought the Generals in late 1983 and immediately went on a spending spree with a series of high-profile negotiations for current NFL players and coaches.31 This generated a ton of media coverage for Trump and the USFL, as the two-year-old league was about to start its second season. (It played in the spring so as not to compete with the NFL.)
As Trump said about the publicity, “I hire a general manager to help run a billion-dollar business and there’s a squib in the papers. I hire a coach for a football team and there are sixty to seventy reporters calling to interview me.” 32
His ownership also led to his first national TV interviews. Win #1—publicity for the Trump brand. Trump also felt this publicity was good for the USFL. Some owners disagreed.
The USFL’s economic plan had been to “keep salaries low, minimize superstar acquisitions, and slowly build the league.”33 Trump’s public spending spree caused tensions with other USFL owners.
Myles Tannenbaum, one of the league’s founders and owner of the Philadelphia Stars, confronted Donald about the spending spree in mid-December. “I’m in the media capital of this country,” Donald replied. “When you’re in New York, you have to win.”
“Donald, in Philadelphia you have to win, too,” Tannenbaum retorted. “You have to win everyplace.”
“I need to win more,” Trump insisted.34
Another USFL owner Ted Taube wrote at the time, “It may be in Don Trump’s best interests to pursue [this] strategy…. But Don’s best strategy for the Generals could be [financially] devastating for the USFL as a whole.”35
But Trump didn’t much care about this cost, as it would be borne by the other owners when their players’ salaries skyrocketed. We know this as Trump shortly thereafter signed All-Pro New York Giants’ linebacker Lawrence Taylor, the NFL’s top defensive player.
Trump signed Taylor even though the USFL’s Philadelphia Stars had the exclusive right to sign Taylor under USFL rules. Ironically, the Giants still had the right to keep Taylor, and they promptly gave him a big raise and paid off Trump (who made a quick profit and a lot of publicity).36 Trump wins. USFL and the other owners lose.
Of course, some owners supported Trump and viewed his publicity as a net plus for the league.
Another example of Trump wanting only to win and not caring about the rules occurred when he signed Heisman Trophy–winning quarterback Doug Flutie to a five-year deal worth up to $7 million. But the USFL had a $2 million salary cap.37 Trump didn’t care. Trump “won” again.
Interestingly, Trump later agreed he “overspent” on Flutie when he didn’t perform well.38
Trump Needed the USFL to Compete with the NFL in the Fall
Trump’s aggressive push to get into the NFL also reflected his win–lose mindset.
Trump wanted to own an NFL franchise and build a New York stadium to house it. This could happen if he either a) bought an NFL team (from 1981 to 1983 he tried buying the Baltimore Colts, but they couldn’t agree on the price, and he also considered buying the Dallas Cowboys in 1983.) or b) bought a USFL team and merged with the NFL.39
But the NFL wasn’t
