The Art of the Flip
For Donald Trump, the dividing lines between friends, foils, and foes are blurry, if not entirely nonexistent. There is no contradiction in his mind as he rapidly rotates people through these categories, because his worldview is fundamentally transactional. Very few things are truly personal with him.
(This is an exclusive preview of chapter 5 in “Trump’s Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox” by Jeffrey Sonnenfeld and Steven Tian. The book is published by Worth Books and will be released on March 31, 2026. Pre-order your copy now: https://worth.com/trumpten/)
This is the art of Trump’s flip: he can let bygones be bygones with astonishing ease. Consider the politicians who crossed Trump, lived to tell the tale, and became stalwart loyalists. Lindsey Graham once called voting for Trump “a choice between getting shot or taking poison,” yet transformed into a fierce defender. “Lil Marco” Rubio went from questioning Trump’s manhood to executing his foreign policy. “Lyin’ Ted” Cruz weathered JFK assassination smears to become a trusted Senate ally. JD Vance went from dubbing Trump “America’s Hitler” to serving as his loyal vice president. To Trump, the ultimate pragmatist, converting critics into useful allies is simply good business.
Followers, Not Friends
Perhaps calling them “friends” is a stretch; Trump has few friends, only followers. He cares almost exclusively about whether you serve a useful purpose for him. Once you cannot, you are discarded. Allies must constantly re-prove their value to avoid outliving their usefulness.
While supporters might frame this as a ruthless meritocracy, critics argue he will abandon a once-useful advisor the moment they slip into irrelevance, regardless of their years of service. Staffers without real constituencies of their own—who rely entirely on Trump for their standing—are treated as interchangeable and immediately disposable.
Redeeming the “Untouchables”
Conversely, Trump is always looking to bring individuals with independent constituencies into his tent. This explains why he routinely defends ostensibly left-in-the-dust losers that polite society shuns.
With these figures, Trump opportunistically “buys low,” calculating how he can benefit from their misfortune. The decisive factor is constituency. He doesn’t ask if someone has morally repented; he asks if they still command an audience that serves his interests—especially if their story fits a narrative of victimization.
This is why Trump defends fallen stars like Martha Stewart, whose indictment aligned with his own grievances against prosecutors; Eric Adams, who retains working-class support; Mike Tyson, who commands a die-hard fandom ; and the Tate brothers, who hold cult status on the extreme right. They remain glamorous and sympathetic to their specific networks. Defending them costs him little, but reaps the reward of their loyal followings.
The Perpetual Need for Foils
The dizzying volatility of Trump’s relationships serves another vital purpose: he constantly needs foils. Without them, his shtick falls apart. For Trump to be Trump, he requires a convenient target du jour for his supporters’ ire. The rage isn’t personal in most cases, and many such targets are later converted into friends and the target might later be flipped into a friend when their usefulness as targets wane and their usefulness as prospective friends increases.
His attacks are deeply intentional. He reads people unfailingly, utilizing an outsider’s instinct for the jugular. His nicknames—“Low-Energy Jeb,” “Lil Marco,” “Lyin’ Ted,” “Crooked Hillary,” “Sleepy Joe”—catch fire because they capture a resonant shred of truth about his opponents’ perceived weaknesses.
The Authentic Social Subversive
Behind the cold logic of Trump’s curated social stage is a genuinely disarming, subversive accessibility that defies all protocol. He relishes inverting social hierarchies in ways no other leader would. He’ll bring world leaders to eat cake and drink Cokes on the Mar-a-Lago patio, surrounded by gawking club members. He crashes strangers’ weddings on a whim to take photos.
Trump is also a relentless connector, delighting in creating collisions between radically different worlds. When I brought some top Chinese CEOs to visit him a year, he didn’t hold a stiff corporate meeting. He called his kids down to parade through the office , then marched the executives to visit his tenants at the New York branch of ICBC, playfully introducing the world’s largest bank as “some little Chinese bank”, bemusing and horrifying his guests in equal doses.
His door is open to almost anyone. He’s just as likely to pull random landscapers off the White House lawn to quiz them on tariffs as he is to consult a CEO. He’ll usher a touring group of HBCU presidents into the Oval Office on the spur of the moment. As MSNBC anchor Stephanie Ruhle quipped: “I called DJT on his cell phone and he picked up first ring, and I said, ‘Yo, can I get an interview?’ And he told me to go f*ck myself, but I still was able to connect with him just like that”. By contrast, she noted, reaching Joe Biden or Kamala Harris requires navigating fifty intermediaries and the Pony Express.
Ultimately, in the Trump solar system, relationships are not built on enduring loyalty, but on immediate leverage and pragmatic utility. By mastering this dizzying fluidity of friends, foils, and foes, Trump ensures that no matter who enters or exits the stage, the spotlight never leaves him.
Pre-order the Book Today
Trump’s Ten Commandments: Strategic Lessons from the Trump Leadership Toolbox reveals that whether he is crushing opponents or charming former rivals, Trump is always playing a calculated game. Beyond the transactional “Fluidity of Friends, Foils, and Foes” explored above, Sonnenfeld unpacks nine other distinct commandments—from his “Wall of Sound” media dominance to his “Hub-and-Spokes” management style. Pre-order here: https://worth.com/trumpten/
