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“Some people have an ability to negotiate. It’s an art you’re basically born with. You either have it or you don’t.” ⁶

—Donald J. Trump

Donald Trump made millions from his starring role in The Apprentice and its progeny. And the publicity and persona he derived from it formed a fundamental basis for the millions more he made from subsequent U.S. and international licensing deals.

His celebrity and brand also proved indispensable to his successful presidential run. He almost certainly would not be president today had he not first been portrayed as such a widely admired and successful business titan in the popular NBC series.

So, how much preparation did he do for his first meeting and negotiation with Mark Burnett, the creator of the hit Survivor reality TV series who pitched The Apprentice concept to Trump?

None. Trump did it all on the fly based solely on his instincts.

According to Michael Kranish and Marc Fisher in their extensively researched and well-written biography Trump Revealed, The Definitive Biography of the 45th President:

Burnett walked out of that first meeting with a handshake deal to make The Apprentice. Trump secured not only a starring role on a show made by TV’s hottest producer but also 50 percent ownership of it. Trump had consulted no one, done no research. He liked the idea; he bought it. It was a classic Trump moment, an example of the gut-instinct decision making that he had proudly touted throughout his career. ⁷

How does this fit into Trump’s business negotiation approach? Two consistent themes run through Trump’s business negotiations:

1) his gut-level planning and decision-making, and

2) his win–lose mindset and approach to business and life.

Trump’s Gut Drove His Business Negotiations—Not Strategic Homework

“I just think that you have an instinct and you go with it. Especially when it comes to deal-making and buying things.” ⁸

—Donald J. Trump

Lack of planning in The Apprentice deal was typical Trump. In 1986, Trump sought to take over Bally’s, a public company that owned three casinos, one in Atlantic City, where Trump already owned two casinos. Trump eventually became Bally’s biggest shareholder after investing $63 million and buying up 9.9 percent of its stock.

His interest in Bally’s originated from Daniel Lee, an analyst at Drexel Burnham Lambert, the infamous Wall Street investment bank led by Michael Milken that went bankrupt in 1990 due to its involvement in illegal activities in the junk bond market.

According to Lee, who informally advised him on this effort, “[Trump had] begun buying the stock without even reading the annual report.” [Emphasis added.]⁹

As with The Apprentice deal, though, Trump’s gut proved profitable. While Bally’s fended him off, he made over $20 million when Bally’s bought him out.

Trump acknowledges this tendency and considers it a strength. In a 1984 interview with Lois Romano of The Washington Post in which he discussed negotiating nuclear disarmament with the then Soviet Union, he said that—while he was no expert on missiles—“it would take an hour and a half to learn everything there is to learn about missiles….I think I know most of it anyway.”¹⁰

President Ronald Reagan, whom no one ever accused of digging deep into the policy details of nuclear disarmament, certainly spent a lot more than an hour and a half strategic prep time before negotiating this with Soviet Leader Mikhail Gorbachev in 1986.

How important is strategic preparation before complex, significant negotiations?

RESEARCH: Harvard Law Professor Robert Mnookin, Chair of the Harvard Program on Negotiation, noted in his excellent book Bargaining with the Devil, When to Negotiate, When to Fight, it’s appropriate to spend around 90 percent of your time in these negotiations “on preparation behind the table.”¹¹

In my training and consulting, I usually recommend at least twice as much time on strategic planning as “at the table” negotiating. Here’s how I describe this crucial element in my book, Gain the Edge! Negotiating to Get What You Want (St. Martin’s Press, 2004) (Gain the Edge!):

The Power of Preparation Always Makes a Difference

What is the most universally ignored but most effective negotiation tool? Preparation. I conclude every one of my seminars with this statement: “Prepare. Prepare. Prepare. It’s guaranteed to succeed. The more you prepare, the better you will do.”… Renowned UCLA basketball coach John Wooden said: “Failing to prepare is preparing to fail.” He’s right…. Negotiation research unmistakably illustrates the concrete value of preparation.¹²

Of course, Donald Trump would dispute the characterization that he doesn’t do his homework.

First, he would likely suggest he does his homework where it’s needed. A perfect example would be his first big real-estate negotiation when he was 27—a complex deal involving multiple parties in which he redeveloped the Commodore Hotel in New York City next to Grand Central Station (now the Grand Hyatt).

He may be right. In fact, his long-time lawyer and co-star of The Apprentice, George H. Ross, in Trump-Style Negotiation: Powerful Strategies and Tactics for Mastering Every Deal (Trump-Style Negotiation), wrote:

Donald Trump spends a great deal of time preparing himself and members of his team for every negotiation—not just for the big deals, but every negotiation he enters. He knows that by being as well prepared as he can be, there will be fewer surprises.¹³

Ross is probably right, at least for the 1970’s Trump. This is confirmed in possibly the most comprehensive Trump biography by Village Voice investigative reporter Wayne Barrett, who met Trump in 1978 and compiled 14 file drawers of documents on Trump and his deals. In Barrett’s 450-page book, Trump: The Greatest Show on Earth published in 1992 (Trump Show), he wrote about Trump’s 1974 purchase of some bankrupt Penn Central railways properties:

[Ned] Eichler and Donald cut the deal over the next six months, winding their way through a 65-page contract and working out a timetable for the first phase of the anticipated zoning changes and housing subsidies that reached 13 years into the future.¹⁴

While Trump probably did his homework early on, he did less as he became more prominent in the mid-1980s and beyond.

Barrett described Trump in the mid-1980s here in two Atlantic City casino negotiations.

The Hilton Castle Casino Acquisition

While the Plaza deal took four years, from Donald’s initial lease negotiations in the spring of 1980 to the grand opening, the Castle acquisition took less than four months…. He proudly boasted that he purchased the Hilton without ever having taken even a walk-through….

The Taj Construction Catastrophe

The catastrophe at the Taj was a symptom of [Trump’s] sudden inability to focus—he’d visited the site rarely and lost contact with the detail work that was once his trademark…. By and large, he’d transcended his Hyatt and Trump Tower days of creating value and repositioned himself as a player in the far less demanding league that merely traded in it. [Emphasis added.]¹⁵

Trump’s loss of focus and attention to detail became increasingly problematic.

Second, Trump would likely indicate that negotiation leaders should delegate to take advantage of their team’s strengths. Doing detail-oriented homework is neither his strength nor in his interest, he might note. That’s why you hire experts and lawyers, right?

Ross would again agree with Trump, noting:

To my knowledge, Donald Trump has no negotiating weaknesses except maybe the fact that he doesn’t like to discuss minor details. He lacks the patience to work on unimportant paperwork, because he likes to focus on the big picture as a more productive use of his time…. Being a smart deal maker, Donald has learned to see the forest and let his subordinates see the trees.¹⁶

Delegation is a critical negotiation strategy. Negotiation leaders should rely on experts and others. But effective negotiation leaders still need to understand the interests, details, and interconnections between the issues to fully appreciate the strategic negotiation landscape.

RESEARCH: Professors Roy Lewicki, David Saunders, and Bruce Barry, co-authors of Negotiation, the world’s bestselling business school negotiation textbook and the gold standard, wrote:

We cannot overemphasize the importance of preparation, and we strongly encourage all negotiators to prepare properly for their negotiations…. Preparation… should be right at the top of the best practices list of every negotiator. Negotiators who are better prepared have numerous advantages.¹⁷

One final note on preparation. So far, we have focused on the substantive preparation for negotiations. Learn the facts.

You also need to do your homework on the negotiation process. Most successful professionals do their due diligence on the facts. But they give short shrift to the process and wing it when it comes to preparing for the actual moves in the negotiation. Do both.

How well has Donald Trump prepared on the substance and process in his negotiations over the years? On a scale of 1 to 10, 10 being the most prepared, I would give him a three. I expect he would agree he’s not much for preparation.

His gut dominates.

Trump’s Win–Lose Mindset Impacted All His Business Negotiations

“We are going to start winning again…. We are going to win so much.”¹⁸

“I have a winning temperament. I know how to win.”¹⁹

“I’m not big on compromise. I understand compromise. Sometimes compromise is the right answer, but oftentimes compromise is the equivalent of defeat, and I don’t like being defeated.”²⁰

“We [the U.S.] don’t win anymore. We don’t beat China in trade. We don’t beat Japan, with their millions and millions of cars coming into this country, in trade. We can’t beat Mexico, on the border or in trade.”²¹

“I win, I win, I always win. In the end, I always win, whether it’s in golf, whether it’s in tennis, whether it’s in life, I just always win. And I tell people I always win, because I do.”²²

“If I’m President, we will win on everything we do.”²³

“My 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 interested in 1984 in merging with the brand-new league. What did Trump do? He convinced his fellow USFL owners to change their go-slow-and-grow strategy by promising either:

A network TV contract for a fall season despite the USFL being in the midst of a multi-year $14 million annual ABC contract for the next few spring seasons. The idea? Head-to-head competition with the NFL in the fall would convince it to merge with the USFL. Or;

A lawsuit against the NFL for antitrust violations for preventing a fall USFL schedule and get a massive judgment forcing a merger.

Trump’s language at the January 1984 USFL owners’ meeting, according to the owners’ meeting notes, reflects Trump’s win–lose mindset:

I guarantee you folks in this room that I will produce CBS and I will produce NBC and that I will produce ABC, guaranteed, and for a hell of a lot more money than the horseshit you’re getting right now…. I don’t want to be a loser. I’ve never been a loser before, and if we’re losers in this, fellows, I tell you what, it’s going to haunt us…. Every time there’s an article written about you, it’s going to be that you owned this goddamn team which failed… and I’m not going to be a failure.⁴⁰

Trump convinced the owners in August 1984 to switch, starting fall of 1986. Unfortunately for the owners, though, it took place after an aggressive media campaign highlighted a nasty personal war between Trump on one side and USFL Commissioner Chet Simmons and Tampa Bay Bandits owner John Bassett on the other.

A Bassett letter to Trump illustrates how Trump interacted with the other owners—his seeming partners with common interests. Bassett, who originally liked Trump, opposed Trump’s strategy but shared interests with him in an ultimate merger with the NFL.

Dear Donald:… I have listened with astonishment at your personal abuse of the commissioner and various of your partners if they did not happen to espouse one of your causes or agree with one of your arguments…. You are bigger, younger and stronger than I, which means I’ll have no regrets whatsoever punching you right in the mouth the next time an instance occurs where you personally scorn me, or anyone else, who does not happen to salute and dance to your tune.⁴¹

Trump’s attitude was win–lose, even with his partners.

The owners interestingly voted to move to a fall schedule despite having commissioned an independent study from McKinsey consulting which found Trump’s strategy assumed events it deemed highly unlikely, including any new TV contract for the fall of 1986. This was because:

NBC said it had no interest in televising the USFL in the fall;

CBS said it wouldn’t be interested for the fall of 1986, but might for 1987 if the USFL’s ratings improved; and

ABC’s contract with the USFL would be breached if the USFL moved to the fall of 1986.

McKinsey’s recommendation? Cut costs, stay in the spring for 1986, launch an ad campaign to drive up attendance and revenue, and consider moving to the fall of 1987 when ABC and CBS might be interested.⁴²

What happened after the owners decided to move to the fall of 1986?

ABC, the only network possibly interested for the fall of 1986, was upset the USFL intended to breach its spring 1986 contract. It thus refused to sign a deal to broadcast any fall 1986 USFL games. CBS and NBC also confirmed their disinterest in televising the USFL’s fall 1986 games.

“Winning” the battle to go to a fall 1986 season also meant that Trump and the USFL would lose their contractually solid deal with ABC to broadcast USFL spring games in 1986.

No television contract for the fall of 1986 basically spelled the end of the USFL, except for a possible antitrust lawsuit against the NFL.⁴³

“Wait,” you might say. “It’s obvious the USFL should have just followed McKinsey’s recommendations and waited to go to a fall 1987 season. Why did these owners vote for Trump’s move for 1986?”

Three reasons. First, the owners were desperate financially. Many might not have even made it to a fall 1987 season. Even Ted Taube, who penned that early letter indicating “Don’s best strategy for the Generals could be devastating for the USFL as a whole,” came around, noting that the USFL had “no other financially viable alternative.”

Second, Trump negotiates and communicates in clear and definitive language with an air of invincibility. He “guaranteed” the TV contracts. Clarity and certainty can be persuasive and convincing. The owners wanted to believe him too.

And third, Trump threatened that if the USFL did not move to the fall, it might find itself playing without him. Since Trump was then practically the face of the USFL, this might spell its doom sooner rather than later.

Trump tactically and smartly negotiated with the other owners to get them to vote for the move, despite their internal strife. All along he demonstrated his win–lose mindset.

One final element of this “move to the fall” effort illustrates Trump’s mindset. Trump in March 1984 secretly met with long-time NFL head Pete Rozelle to discuss the NFL–USFL relationship.⁴⁴

We know about this negotiation as it became a major element of the USFL’s antitrust lawsuit against the NFL. And Rozelle and Trump testified about it under oath.

Rozelle also a) wrote a memo to his file immediately after describing what occurred, and b) discussed it later with the NFL’s finance chairman. This foreshadows former FBI Director James Comey’s testimony about his Trump meetings in 2016 and 2017, where he also wrote file memos about his meetings and discussed them with his FBI colleagues.

Trump wrote no such memo nor discussed this meeting with any colleagues. (According to his testimony he said, “I would have considered notes to be a very unnatural thing to do. People don’t go around making notes of conversations in my opinion.”)

What happened at the Trump–Rozelle meeting that illustrates Trump’s win–lose mindset? We have conflicting versions of it.

According to Trump’s testimony:

Rozelle promised him an NFL team if he would help keep the USFL in the spring and stop an antitrust lawsuit;

Trump responded there is “no way I am going to sell out [my fellow USFL owners]” and would only consider an NFL team as part of a merger with “four or five or six teams” coming in from the USFL (18 USFL teams then existed); and

Rozelle told him he would explore the possibility of at most one or two teams and get back with Trump.

According to Rozelle’s testimony:

– Trump started the meeting by threatening an antitrust lawsuit, but noting he didn’t want to sue;

– Trump said he really just wanted an NFL expansion team for himself in New York;

– Trump said if the NFL did not agree right away to his demands, he would sue and would become too committed to the USFL to walk away and cut a separate deal;

– Trump offered to identify two or three other USFL owners Rozelle might reward with franchises; and,

– Rozelle would get back with Trump on the possibility of adding one or two more teams later.⁴⁵

Regardless of who you believe, two things are clear: One, Trump offered to throw at least 11 of his fellow USFL owners under the bus in exchange for an NFL team in New York. And two, Rozelle would consider adding one or two teams—including one for Trump—and get back to him.

Both support the following conclusion: Either Trump wins and 11 or more USFL owners lose, or no one wins.

Of course, Trump might respond that those other USFL owners could not have financially qualified for NFL teams anyway. So, he wasn’t “selling them out,” right?

Wrong. The purpose of the meeting, which took place at Trump’s request and unbeknownst to the other USFL owners, revolved around an NFL franchise for Trump.

Had Trump cared about other USFL owners getting NFL franchises, he would have informed at least some of them of his Rozelle meeting. By keeping the meeting secret, even from his “partners,” he maintained his ability to accept an NFL franchise in the future without publicly stabbing his fellow USFL owners in the back.

But Rozelle later rejected any deal. So, it was on to litigation—another negotiation strategy that reflects Trump’s zero-sum win–lose mindset.

Trump’s Last Shot for an NFL Team—Sue!

Litigation represents the ultimate win–lose approach to satisfying parties’ interests. Why? The final judge or jury in litigation almost always has only one choice at the end of the trial: One side wins and one side loses. Any other solution to the dispute, a negotiated settlement, must be agreed upon by the parties.

Trump understands this. In fact, his love of litigation borders on the legendary. It’s public record that Trump has been a party in over 4,000 litigation matters prior to becoming President.⁴⁶ He has sued over 1,900 times. Since he effectively took control of the Trump development business in his late 20s, this comes to either suing or being sued an average of over 90 times per year.

This time he and the USFL sued the NFL for antitrust violations, alleging the NFL used its monopoly power to prevent the networks from televising USFL games starting in the fall of 1986. This destroyed the USFL, they alleged.

They sought hundreds of millions of dollars in damages, hoping a favorable verdict would force a merger.

Two elements here reflected Trump’s win–lose attitude. Each furthered his goal to build his brand and generate maximum publicity for Donald Trump.

Trump Chose an Attack-Dog Win-at-All-Costs Litigator

Trump pulled a fast one on his fellow USFL owners by announcing the lawsuit at a press conference with no invited USFL representative and selecting his long-time lawyer Roy Cohn to litigate it.

Other than Trump’s father, Roy Cohn more than anyone contributed to Donald Trump’s business and personal success.

A bit of history: Roy Cohn came to fame as U.S. Sen. Joseph McCarthy’s right-hand man in the 1950s. McCarthy made headlines then by leading a public and political witch hunt to ferret out alleged Communist Party spies and subversives who had supposedly infiltrated all levels of the U.S. government and society.⁴⁷

“McCarthyism” became one of our country’s most embarrassing historical episodes. Sen. McCarthy was ultimately censured by the Senate, and Cohn forced to resign as McCarthy’s Chief Counsel of the Senate’s Permanent Subcommittee on Investigations.

Cohn would later say he “had never worked for a better man or a better cause.”⁴⁸

Cohn subsequently returned to practice law in New York City and became one of its most influential men, wielding enormous political influence and representing clients ranging from the Catholic archdiocese to the mob.

He was no saint either. Cohn, according to Trump Revealed, “in the two decades following the McCarthy hearings…was indicted on charges ranging from obstruction of justice to bribery to extortion, but he always seemed to get off. To fight his legal battles, [he] honed a set of hard-boiled tactics and a rhetorical style that would serve him far beyond the courtroom.”⁴⁹

Trump biographer Barrett called Cohn “a walking advertisement for every form of graft, the best-known fixer in New York.”⁵⁰

The point here is not to impugn Trump’s character by associating him with Cohn. Instead, it is to illustrate that Trump—who had first hired Cohn in 1973 to defend him in a U.S. Justice Department lawsuit alleging racial discrimination in Trump’s apartment buildings—hired an extremely aggressive win–lose mad-dog litigator.

Cohn’s litigation and approach to life can be summarized as “go to hell” and “when attacked, counterattack with overwhelming force.”⁵¹

“Don’t Mess with Roy Cohn,” a 1978 Esquire magazine profile of Cohn written with his cooperation stated that he fought every case as if it were a war and, “Prospective clients who want to kill their husband, torture a business partner, break the government’s legs, hire Roy Cohn….He is a legal executioner—the toughest, meanest, loyalest, vilest, and one of the most brilliant lawyers in America.”⁵²

Trump was quoted in Esquire saying, “when people know that Roy is involved, they’d rather not get involved in the lawsuits and everything else that’s involved.” ⁵³

Trump later hired another lawyer of the same ilk to try the NFL case when Cohn got sick, Harvey Myerson. Myerson would later spend 70 months in prison for tax evasion and other crimes in what prosecutors labeled “a one-man crime wave.”⁵⁴

Significant benefits can attach to a highly aggressive adversarial litigation approach. A win–win mindset and/or result is not one of them. It’s win–lose with litigators like this.

The Jury and Appellate Court’s Decisions

Trump and the USFL won the case and that final battle. And they got a ton of publicity. But they lost the war.

What happened? The jury concluded the NFL inappropriately used its power to prevent the USFL from competing with it. But they only awarded the USFL $1.00 in damages. Here’s what happened in the six-person jury room, according to juror interviews:

– Two jurors felt the NFL had harmed the USFL and deserved hundreds of millions of dollars;

– Two jurors felt the USFL’s lawsuit was just a desperate effort to stay alive; and

– Two jurors initially were undecided, one of whom was Patricia Sibilia—who felt that the NFL acted like a monopoly and engaged in predatory action but that the USFL had overspent and was partially responsible for its own demise, violating their TV contract by moving to the fall season.

Regarding Trump, Sibilia, who brokered the ultimate compromise, “decided she didn’t like Trump, whom she’d barely heard of before the trial. ‘He was extremely arrogant and I thought that he was obviously playing the game,’ Sibilia recalled. ‘He wanted an NFL franchise….The USFL was a cheap way in.’” ⁵⁵

The U.S. Second Court of Appeals upheld this verdict, noting “what the USFL seeks is essentially a judicial restructuring of major league professional football to allow it to” merge with the NFL. The decision stated, in a passage relevant to the win–lose litigation strategy pursued by Trump and the USFL:

The jury in the present case obviously found that patient development of a loyal following among fans and an adherence to an original plan that offered long-run gains were lacking…. The jury found that the failure of the USFL was not the result of the NFL’s television contracts but of its own decision to seek entry into the NFL on the cheap.⁵⁶

Donald Trump described his USFL experience this way,

I bought a losing team in a losing league on a long shot. It almost worked, through our antitrust lawsuit, but when it didn’t, I had no fallback. The point is that you can’t be too greedy. If you go for a home run on every pitch, you’re also going to strike out a lot…. If there was a single key miscalculation I made with the USFL, it was evaluating the strength of my fellow owners. In any partnership, you’re only as strong as your weakest link.⁵⁷

Another win–lose mindset hallmark: If you win, take credit; if you lose, blame your partners.

Two final notes on Trump’s win–lose mindset. One, George Ross, his long-time lawyer, would disagree with the conclusions here. Ross notes that “the recurring theme in Trump-style negotiation is looking for ways to satisfy both sides, to structure a deal so that everyone feels that he or she comes out a winner.”⁵⁸

In fact, Ross concludes his book by stating: “Just remember this most important element of Trump-style negotiation: You can only achieve mutual satisfaction and complete the biggest and best deals when you build a relationship of trust and rapport with those with whom you become involved.”⁵⁹

Ross’ statement regarding mutual satisfaction is true. Does Trump believe this? Not according to the evidence. Does Ross himself really believe Trump brings a win–win mindset to negotiations? The example he cites in his book after this statement does not even involve Trump.

Plus, the USFL negotiation and Trump’s many negotiations detailed later illustrate his dominant negotiation mindset: win–lose.

It’s also important to examine what constitutes a “win” here in Trump’s eyes. If Trump measures wins financially, he admittedly lost $22 million here.⁶⁰

A better financial deal would have been the Cowboys. He could have bought the NFL Cowboys in 1984 for $85 million. (It sold then for $85 million.) Its owners then turned around and sold it to its current owner in 1989 for $170 million. Forbes in 2017 declared the Cowboys the most valuable sports franchise in the world at $4.8 billion.⁶¹

But Trump didn’t think in purely financial terms. He said in January 1984, shortly after buying the Generals, “I feel sorry for the poor guy who is going to buy the Dallas Cowboys. It’s a no-win situation for him, because if he wins, well, so what, they’ve won through the years, and if he loses…he’ll be known to the world as a loser.” ⁶²

Trump became “known to the world” and gained his first national exposure for his name and brand during this time. He also gained a reputation as the wealthy New York developer who took on the uber-powerful NFL. That’s a win for him.

On the other hand, he didn’t end up owning an NFL team.

Bottom line—Trump views negotiations and life with a win–lose, zero-sum mindset.

As John “Jack” O’Donnell, President of the Trump Plaza Hotel & Casino in the late 1980s recalled after working closely with Trump in Atlantic City, “Trump had a simple mindset, winners versus losers, and…his chief motivation was winning, even when he didn’t need the money.” ⁶³

And Trump himself stated: “Man is the most vicious of all animals, and life is a series of battles ending in victory or defeat. You can’t let people make a sucker out of you.” ⁶⁴

LESSONS LEARNED

Trump’s Strategies and Tactics	Gut-level decisions drove Trump’s negotiations, not strategic planning.
A strictly win–lose mindset impacted all Trump’s negotiations.
Lessons Learned	Strategic preparation based on the experts’ proven research—not guts and instincts—should drive our negotiations.
Detailed preparation and homework behind-the-table should involve two to nine times more time than at-the-table negotiating.
Preparation on the process of negotiation—not just learning the facts—is critical to success.

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