The Trump Leadership Playbook–And Why It Matters

Article Summary: 

It’s no surprise that Donald Trump is an unconventional leader, but it’s less obvious that he’s operating from the leadership playbook of his former fixer, Roy Cohn. And with big implications. Here Gregg Vanourek looks at this topic from a leadership perspective.

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Donald Trump’s approach to leadership is unconventional. To understand his leadership playbook, we need to back up and examine how his former fixer and mentor influenced him.

 

A Fixer and His Client

Roy Cohn was famous for being Donald Trump’s “fixer” (well before Michael Cohen arrived on the scene). Since most of us don’t have one, it’s fair to ask: What’s a fixer?

A fixer is someone who solves problems for others, no matter what it takes. Their methods don’t matter. Morality and the law are beside the point. The key is getting things done. Often, it’s the dirty work (e.g., hush money payments).

A fixer is somewhat akin to what’s called a “cleaner” in the mafia but not usually as extreme. (In a nutshell, cleaners remove incriminating evidence, eliminate witnesses, and hide the bodies.)

Cohn famously had a huge impact on Donald Trump, given their close personal and professional relationship over many years. Hand in glove with his fixer duties, Cohn mentored Trump and also represented him legally. The start of it all: In 1973, when Trump was in his late twenties, Cohn began representing the Trump family and their businesses in response to a U.S. Department of Justice lawsuit accusing them of racist and discriminatory rental practices in their New York City apartments, including allegedly marking rental applications with a “C” for “colored,” in violation of the Fair Housing Act.

 

Close Relationship & Influence

Cohn and Trump were close. Cohn called Trump his best friend and told the media that Trump used to call him 15 to 20 times a day at times. Trump started talking like Cohn, using his phrases. Before Cohn died, Trump was the last person to speak with him on the phone, according to Cohn’s long-time colleague Christine Seymour. And Cohn introduced Trump to political operatives Roger Stone and Paul Manafort.

Cohn’s influence on Trump isn’t hard to spot. “All I can tell you,” said Trump about Cohn to a Vanity Fair writer, “is he’s been vicious to others in his protection of me.” When Attorney General Jeff Sessions recused himself from the Russia probe in 2017, exposing Trump to more risk, Trump reportedly asked,

“Where’s my Roy Cohn?”

 

The Making of a Fixer

So, who was Roy Cohn? He grew up in a wealthy family as an only child and was “incredibly spoiled,” according to his cousin, who added, “He always got his way.” Cohn became Chief Counsel to Senator Joseph McCarthy during the “Red Scare” period in the 1940s and 1950s. He represented mafia bosses (including John Gotti, Tony Salerno, and Carmine Galante), media mogul Rupert Murdoch, and others.

Cohn was famous for not paying people back. He bragged openly about not paying his taxes. He was indicted four times (for perjury, bribery, conspiracy, extortion, blackmail, filing false reports, obstructing justice, stock swindling, and more), but he was acquitted three times, with the fourth ending in a mistrial. It’s fair to wonder whether it was vindication or evidence of his penchant for beating the system.

In 1986, Cohn was disbarred as a New York attorney based on accusations of “dishonesty, fraud, deceit, and misrepresentation” related to four cases over decades, including misappropriating a client’s escrowed property, trying to defraud a dying client by forcing him to sign a will amendment that would enrich Cohn by making him a co-executor, failing to pay a client’s loan back, and lying on his D.C. bar application.

Over the years, those who have known, worked with, or investigated Cohn have described him as follows: “sinister,” “savage,” “amoral,” and “ruthless.” “You knew when you were in Cohn’s presence,” said an attorney who knew him for years, “you were in the presence of pure evil.” They’ve called him an “intimidator,” a “political hitman,” an “expert at media manipulation,” a “quintessential hypocrite,” “a scoundrel,” and “a snake” who “will stop at nothing”—as well as a closeted and homophobic “gay man who persecuted other gay people.” He died of AIDS in August 1986 but refused to admit he had it. The IRS then seized almost all of his assets, from his home and cars to his bank accounts and other personal assets.

 

A Fixer’s Playbook

A big part of Cohn’s legacy is the influence of his teachings on Donald Trump, a playbook of sorts. He was expert at manipulating the media and planting stories in the tabloids. Cohn taught Trump how to find and exploit legal loopholes and vulnerabilities in the justice system. His approach involved no apologies, no shame, and no remorse. Never giving an inch on anything.

If you’re in legal trouble, start by denouncing the judge. Threaten their family. Better yet, get the judge in your pocket. “I don’t want to know what the law is,” Cohn would say. “I want to know who the judge is.”

Cohn famously taught Trump to “attack, counterattack, and never apologize.” Always attack, never defend, and never concede defeat. He viewed fear and chaos as valuable weapons in law and politics. Aggression and intimidation were also useful tools. Cohn was big on what he called “scare value” when it came to manipulating people or forcing them to back down. When accused, turn the tables and attack your accuser. Countersue.

Beneath it all was a zero-sum view of life in which winning is everything. (1) Winners are fighters who leverage power and exploit vulnerabilities. How? By using people, and by spotting suckers and playing them. Through public manipulation. Plausible deniability. Crafting narratives and controlling the media. Blurring lines so people can no longer tell what’s real. Cohn gave Trump a blueprint for creating and curating his public image and countering criticism with combative pushback. Confrontation and defiance. Ferocious retaliation and threats.

Cohn also taught Trump a distinctive viewpoint about loyalty and betrayal: First, winners require loyalty (or even devotion) from everyone they work and associate with, both personally and professionally. Second, they need not reciprocate that loyalty. They throw people under the bus when it suits them. Everything is transactional. Cutthroat. (True to form, Trump abandoned Cohn in the end, when Cohn was in physical and mental decline. He “dropped him like a hot potato,” according to Susan Bell, Cohn’s secretary.)

Surely, Cohn had some redeeming qualities as well, including a fierce intellect. No doubt, the public record doesn’t fully capture the nuances of his life, the pains he suffered, or all the good he did in some cases. But overall, a clear picture emerges of a deeply flawed man with a dark and cynical worldview. To see that, we need only turn to Cohn himself in his own words.

 

Roy Cohn in His Own Words

The following are quotes by Roy Cohn from his books or public statements:

• “I decided long ago to make my own rules.”
• “Power is not given, it is taken. And I will take it.”
• “The pursuit of power is the ultimate adventure.”
• “I am willing to fight for what I believe in, no matter the consequences.”
• “I am a master manipulator, able to bend people to my will.”
• “True power lies in controlling the narrative.”
• “Fear is a powerful motivator, and I know how to use it to my advantage.”
• “Justice is a concept I have redefined in my own image.”
• “It’s not about being liked, it’s about being respected and feared.” (2)

What does it reveal about Trump that he would choose this man as a friend, fixer, and mentor? As the proverb goes:

“Tell me who your friends are, and I will tell you who you are.”

Trump has been in the public eye for a long time, from Trump Tower and The Art of the Deal to “The Apprentice” and the Oval Office. We’re all familiar with his quirks and antics. Once you learn about the Roy Cohn playbook, though, things start falling into place. You see how Trump follows the playbook closely, though with his own flourishes. For evidence, let’s turn to Trump himself.

 

Trump in His Own Words

Here is Donald Trump in his own words from his books and public statements:

• “Rules are meant to be broken.” -Donald Trump, Midas Touch
• “My motto is: Always get even. When somebody screws you, screw them back in spades.” -Donald Trump, Think Big: Make It Happen in Business and Life
• “Unite to win. Divide to conquer.” -Donald Trump, Midas Touch
• “There’s an old German proverb to the effect that ‘fear makes the wolf bigger than he is,’ and that is true.” -Donald Trump, Think Like a Champion
• “When I look at myself in the first grade and I look at myself now, I’m basically the same. The temperament is not that different.” -Donald Trump
• “The best thing I know about me, is that I’m rich.” -Donald Trump
• “The final key to the way I promote is bravado. I play to people’s fantasies.” -Donald Trump, Trump: The Art of the Deal
• “He’s not a war hero, he’s a war hero because he was captured. I like people who weren’t captured, okay?” -Donald Trump, July 18, 2015, in Ames, Iowa, when asked about the naval service of U.S. Senator John McCain
• “Show me someone without an ego, and I’ll show you a loser.” -Donald Trump
• “All I want to do is this: I just want to find 11,780 votes…. I only need 11,000 votes. Fellas, I need 11,000 votes. Give me a break…. It’s just not possible to have lost Georgia. It’s not possible.” -Donald Trump on a January 2, 2021, call with Georgia Secretary of State Brad Raffensperger
• “And after this, we’re going to walk down, and I’ll be there with you, we’re going to walk down… Because you’ll never take back our country with weakness. You have to show strength and you have to be strong…. I know that everyone here will soon be marching over to the Capitol building to peacefully and patriotically make your voices heard…. This is a time for strength…. And we fight. We fight like hell. And if you don’t fight like hell, you’re not going to have a country anymore…. So let’s walk down Pennsylvania Avenue.” -Donald Trump speech at the Ellipse, January 6, 2021
• “…that was a day of love…. Nothing done wrong at all.” -Donald Trump, October 16, 2024 at a Univision town hall when asked about the January 6, 2021 assault
• “You know, the wall is built…. We did a great job in the wall.” -Donald Trump speech at the Ellipse, January 6, 2021
• “A Massive Fraud of this type and magnitude allows for the termination of all rules, regulations, and articles, even those found in the Constitution.” -Donald Trump post on his Truth Social platform, December 2022
• “Please blame it on me. Please.” “A Border Deal now would be another Gift to the Radical Left Democrats.” -Donald Trump statements on why he urged lawmakers to kill the 2024 bipartisan immigration bill
• “You know, it really doesn’t matter what (the media) write as long as you’ve got a young and beautiful piece of ass.” -Donald Trump
• “Yeah that’s her with the gold. I better use some Tic Tacs just in case I start kissing her. You know I’m automatically attracted to beautiful… I just start kissing them. It’s like a magnet. Just kiss. I don’t even wait. And when you’re a star they let you do it. You can do anything…. Grab them by the p*ssy. You can do anything.” -Donald Trump to TV host Billy Bush in a 2005 video clip
• “We pledge to you that we will root out the communists, Marxists, fascists, and the radical left thugs that live like vermin within the confines of our country.” -Donald Trump in Claremont, New Hampshire, November 2023 (3)
• “It’s poisoning the blood of our country.” “…we got a lot of bad genes in our country right now.” -Donald Trump (4)
• “Proud Boys, stand back and stand by.” -Donald Trump, when asked during a debate if he’d condemn militia and white supremacist groups

Of course, it’s not just Trump’s words that matter but also—even more so—his actions.

 

Trump’s Actions: Accomplishments & Missteps

No doubt Trump has many accomplishments. For example, he grew the Trump family real estate business substantially and has accumulated vast amounts of wealth. He has a valuable brand and co-produced and starred in “The Apprentice,” a popular reality T.V. series. He clearly has a knack for marketing and branding.

Trump went from being a political outsider to U.S. president. Notably, he realigned the Republican Party from a conservative, principle-driven, free-market, free-trade, strong-alliance, family-values party to a nationalist-populist, personality-driven “Make America Great Again” movement (comprised especially of non-college-educated white working-class voters, particularly men, from rural and suburban areas, as well as older voters). His administration passed major tax cut legislation, helped the U.S. move toward energy independence, and mediated the Abraham Accords in the Middle East.

Trump has also had many missteps and failures, many of them disturbing and shocking. His failed business ventures include Trump University (fraud allegations and a $25 million settlement), Trump Airlines (sold in bankruptcy), Trump Steaks (discontinued), Trump Vodka (disappeared), Trump Magazine (folded after a few issues), Atlantic City casino ventures that filed for bankruptcy, and more. He’s famous for stiffing vendors.

 

Trump’s Legal Problems

Here are examples of Trump’s legal problems:

• a 2024 jury finding him guilty in a criminal conviction (the first-ever for a former U.S. president) of all 34 charges of falsifying business records in his hush money trial related to the 2016 election campaign and adult film star, Stormy Daniels
• a 2023 ruling that Trump committed fraud by overvaluing his assets for years
• a 2023 ruling that Donald Trump was liable for sexually abusing E. Jean Carroll (awarding her $5 million in damages for sexual battery)
• 2023 charges for mishandling classified documents after leaving office (including alleged unlawful retention of national defense information and obstruction of justice)*
• a four-count 2023 federal indictment regarding the election, including conspiracy to defraud the U.S. and obstruction of an official proceeding*
• a 2023 Georgia indictment for alleged attempts to overturn the 2020 election (including election interference and racketeering)*
• Trump Organization tax fraud (found guilty in 2021 of tax fraud and other financial crimes)
• dissolution of The Donald J. Trump Foundation for misusing charitable funds for personal and political purposes

* Cases ongoing.

On the personal front, he’s famous for frequent lying and for having an obsession with his net worth and his position on the Forbes Billionaires list. He surreptitiously called journalists in the 1990s using the fake name, John Barron, pretending to be his own publicist. The idea was to plant stories and build up his image, including, again, claims about his net worth. He also has a fixation with crowd sizes at his rallies, and he famously and cruelly mocked a reporter’s physical disability at a rally.

 

The Political Front

On the political front, Trump is the only U.S. president who’s been impeached twice. The national debt grew from about $19.9 trillion when he began his presidency to a record $27.8 trillion when he left office (with tax cuts, government spending, and Covid spending as the big drivers of that historic increase).

The January 6 violent and deadly assault on the U.S. Capitol, with support from far-right extremist groups like the Oath Keepers and Proud Boys, was fueled by his incessant lies about the 2020 election and his inflammatory rhetoric.

“Power is not given, it is taken.”
-Roy Cohn

And then his outrageous and unforgivable delays in taking action to stop the violence and call off his supporters. The result: several deaths, 174 police officers and many others injured, terrible destruction and even defecation in “the People’s House,” mob calls to hang Mike Pence and Nancy Pelosi, hundreds of court cases, and lasting trauma inflicted on police officers, citizens, and our nation.

NEVER ADMIT WRONG.

“…that was a day of love…. Nothing done wrong at all.”
-Donald Trump, October 16, 2024 at a Univision town hall when asked about the January 6, 2021 assault

NEVER CONCEDE DEFEAT.

The attack, all premised on the playbook of never conceding defeat, threatened our democracy, endangering the peaceful transition of power between presidents—a bedrock of our Constitutional order—and was one of the worst stains on the American story.

By following this playbook (and signaling he’ll do it again this year if he loses the election), he’s showing a willingness to divide, damage, and endanger the country in his quest to return to power. Republican politicians must show total absolute loyalty to Trump and his big lie or risk his wrath and a career-threatening primary challenge from a MAGA loyalist. LOYALTY AND BETRAYAL.

“True power lies in controlling the narrative.”
-Roy Cohn

 

The Trump Leadership Playbook: Thought Experiments

We’ve seen the influence of the Roy Cohn playbook on Trump’s words and deeds. Given the strange phenomenon of normalization and acceptance that’s occurring where people are shrugging off things like felony convictions, impeachments, the Capitol assault, and a call to terminate the Constitution, it’s worth doing some thought experiments to see what impacts this playbook would have in other settings. A few examples:

Birth of American democracy: What if on March 4, 1797, George Washington used the Cohn-Trump playbook and shrewdly held on to power instead of willingly, peacefully, and graciously transferring the power of the presidency to John Adams?

Civil War: What if Abraham Lincoln had sought revenge and retribution against the South after the Civil War instead of focusing on healing and uniting the nation?

Cuban Missile Crisis: Imagine if President John F. Kennedy chose bravado, aggressive confrontation, and threats instead of engaging in calm deliberation and seeking the counsel of his National Security Council to defuse a tense and dangerous nuclear standoff with the Soviet Union.

Little League baseball: Imagine your eight-year-old son’s team loses the championship game at the local ballpark and the coach disputes the loss, contesting the result. In a fit of rage, members of the team destroy the dugouts, ransack the snack shack, and tear up the field.

Super Bowl: What if star quarterback Patrick Mahomes announced in advance of a Super Bowl that there’s no way the Chiefs can lose unless the other team cheats—and then accuses the National Football League of fraud if his team loses?

“I decided long ago to make my own rules.”
-Roy Cohn

 

Conclusion

In leadership, character matters more than anything else. By far. Leaders’ worldviews deeply influence how they lead and, of course, the impact they have on followers.

Roy Cohn left Donald Trump a doozy of a playbook, and Trump took it and ran with it. No doubt it’s contributed mightily to this strange, chaotic, disturbing, and exhausting political chapter we’ve been living in for almost a decade. A chapter of darkness and extraordinary division, even among good and kind people who love their country, take pride in its accomplishments, and have so much in common when it comes to shared values and aspirations.

Is it a playbook fit for the presidency? (5)

 

Tools for You

• Leadership Derailers Assessment to help you identify what’s inhibiting your leadership effectiveness
• Personal Values Exercise to help you determine and clarify what’s most important to you
• Alignment Scorecard to help you assess your organization’s level of alignment

 

Related Articles

• “Toxic Leaders, Susceptible Followers”
• “The Problem of Bad Leaders—And Why We Keep Following Them”
• “The Root Causes of Ethical Failings (and Our Political Dysfunction)”
• “The Importance of Integrity in Leadership”
• “The Importance of Credibility in Leadership”
• “What to Do If You Work for a Toxic Boss”
• “Why Are We Talking about Ethics?”
• “The Essential Qualities of Servant Leadership”
• “The Case for Love-Based Leadership”

 

Appendix: The Influence of Trump’s Context

Surely, there have been other influences on Trump’s leadership playbook, from his upbringing and his father’s legal troubles to his advisors. Another potentially overlooked one is the business context he operated in. When Trump was most active with his real estate, hotel, and casino businesses during the 1980s and 1990s, those New York City and Atlantic City industries were rife with organized crime, political corruption, and scandals. Common practices ranged from intimidation and loan sharking to money laundering, bribery, and extortion. There was collusion between developers and city politicians, including developers bribing city officials to secure permits, zoning changes, and other favorable treatment. Tough industries, to be sure, but ones that he chose. It’s fair to wonder the extent to which that context also influenced his worldview and leadership approach.

 

Postscript: Quotations on Leadership Playbooks & Worldviews

• “Character is destiny.” -Heraclitus, ancient Greek philosopher
• “Power tends to corrupt, and absolute power corrupts absolutely.” -Lord Acton, English historian and politician
• “The supreme quality for leadership is unquestionable integrity. Without it, no real success is possible, no matter whether it is on a section gang, a football field, in an army or in an office.” -Dwight D. Eisenhower, U.S. president and five-star Army General
• “Integrity is the most important characteristic of a leader, and one that he or she must be prepared to demonstrate again and again.” -Warren Bennis, leadership author
• “Ninety percent of all leadership failures are character failures.” -Stephen R. Covey, author, executive, and teacher
• “There are no easy answers, but there are simple answers. We must have the courage to do what we know is morally right.” -Ronald Reagan, U.S. president
• “Character, in the long run, is the decisive factor in the life of an individual and of nations alike.” -Theodore Roosevelt, conservationist, writer, and U.S. president
• “Leadership is character and competence. If you can have only one, opt for character.” -Norman Schwarzkopf, U.S. Army General
• “The most important human endeavor is the striving for morality in our actions. Our inner balance and even our very existence depend on it.” -Albert Einstein, German-born theoretical physicist
• “A moderately bad man knows he is not very good: a thoroughly bad man thinks he is all right…. Good people know about both good and evil: bad people do not know about either.” -C.S. Lewis, Mere Christianity
• “There is no safety for honest men except by believing all possible evil of evil men.” -Edmund Burke, Anglo-Irish philosopher and statesman

“Ultimately, an organization cannot be excellent without being ethical….
“There is… one hard and fast rule: triple crown leaders do not compromise on the ethical imperative. Once they do so, they have stepped onto a slippery slope. Ethical compromises set a bad precedent, communicate a reverberating message, undermine credibility, and will likely come back to haunt them many times over. Leaders have to draw the line.”
-Bob and Gregg Vanourek, Triple Crown Leadership: Building Excellent, Ethical, and Enduring Organizations

 

References

(1) In the leadership literature, there’s a word for that: “teleopathy” (a pathological pursuit of an aim). It’s linked with unethical behavior. Source: Goodpaster, K. (2004): Ethics or excellence? Conscience as a check on the unbalanced pursuit of organizational goals. Ivey Business Journal. See also “The Root Causes of Ethical Failings.”

(2) Cohn also said that “Donald Trump pisses ice water” (referring to how ruthless Trump was). Cohn also said, “No public man can indefinitely survive in the center of controversy.”

(3) The word “vermin” is a notable and controversial choice for Trump and his speechwriters to use because the word is well known for its usage in contexts of genocide, ethnic cleansing, and the Holocaust. Historians have noted that Hitler and Mussolini famously called people “vermin.” The idea was to dehumanize certain groups, signaling to the in-group that the outsiders are inferior based on race or other factors. (See U.S. high school history textbooks.)

(4) Historians have noted that “blood poisoning” is a direct quote from Hitler: “All great cultures of the past perished only because the originally creative race died out from blood poisoning.” -Hitler in “Mein Kampf”

(5) Some struggle with this question because they’re concerned the alternative might be worse. After all, the U.S. has two political parties, setting up an essentially binary choice in elections (excepting for minor third-party challenges). “Leaders’ values aren’t judged just by the everyday choices they make,” writes Harvard Business School professor Gautam Mukunda. “They’re measured most importantly by what they do when every option seems like a bad one.” It’s fair to question the basis on which one might believe the other side is worse when the Cohn-Trump playbook is public manipulation, plausible deniability, crafting narratives, controlling the media, blurring lines, breaking rules, dividing to conquer, never giving an inch, never conceding mistakes or defeat, and fighting like hell. The fact remains that Trump had his day(s) in court with more than 60 cases. Our judicial system functioned as designed, and Trump lost. At some point, one might want to reconsider whether to continue believing the claims of the person who follows the playbook of deception, denial, and division—as well as his enablers in this era of misinformation and disinformation. And if you’re worried about policy issues, recall that we have a federalist system with checks and balances. Even if one party controls the presidency, House, and Senate (which is rare), there’s still a Senate cloture rule, requiring 60 votes to end a filibuster.

 

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This article is by Gregg Vanourek, a writer, teacher, and TEDx speaker on personal development and leadership. He is co-author of three books, including Triple Crown Leadership: Building Excellent, Ethical, and Enduring Organizations (a winner of the International Book Awards written with his father, Bob Vanourek). Check out Gregg’s Leadership Derailers Assessment or get his monthly newsletter. If you found value in this, please forward it to a friend. Every little bit helps!