Unboxing the Odd Couple: Trump and Bolton
If politics is theater, then the Trump White House during John Bolton's tenure was The Odd Couple rebooted for the Situation Room. One man, a seat-of-the-pants improviser with no patience for homework; the other, a rigid hawk convinced that order, detail, and discipline are the only antidotes to chaos.
Donald Trump was Oscar Madison — brash, impulsive, trusting his gut and his charm. John Bolton was Felix Unger — meticulous, humorless, and convinced that the room wouldn't function unless everyone color-coded their notes.
The Dealmaker and the Doctrine
Trump has always been the boss — the dealmaker who believes relationships move the world. To him, Xi Jinping isn't China; he's "my friend Xi." Kim Jong-un isn't a dictator; he's the guy who sends "beautiful letters." Trump's foreign policy was personal chemistry first, strategy later.
Bolton is OCD on steroids. He entered the West Wing from a home office that, in all the YouTube interviews, looks like everything is glued in place. He was convinced that the world without his deep understanding of geography, history, doctrine would cease to spin on its axis. He didn't see himself as an adviser but as a tutor, there to educate a president he deemed dangerously uninformed.
Never mind that Bolton had been catastrophically wrong about Iraq — a trillion-dollar, twenty-year mistake that destabilized the Middle East. He was front and center on the cheerleading squad for that fiasco. His acknowledgment? "Some mistakes were made." That's like saying atomic bombs go boom!
When Worlds Collide
The misalignment showed up everywhere, but nowhere more perfectly than on Air Force One flying to Europe for an important meeting. I imagine that Trump just wanted to unwind and watch the soccer game. Bolton saw a ten-hour captive audience for another lecture on transatlantic security frameworks.
I've heard John Bolton tell this story many times. It's comical to think of how the two people had such different views of the situation. Bolton was mad that Trump was not listening to his lecture the whole trip and kept fading in and out between his lecture and watching the soccer match. Trump was probably looking for the eject button for Bolton's seat.
The policy clashes followed the same pattern:
North Korea: Trump believed he could charm Kim into a historic deal. Bolton saw appeasement and pushed "maximum pressure."
Iran: Bolton treated every provocation as an argument for escalation. Trump, wary of a war that could tank his reelection chances, balked.
Afghanistan: Trump wanted a headline-grabbing withdrawal. Bolton warned of chaos, lecturing in circles until Trump tuned him out.
Trump thrives in chaos; Bolton seeks order. Neither had the wiring to meet the other halfway.
Trump on Bolton
By mid-2019, Trump was mocking him as "Mr. Warmonger."
I think it's fair criticism. Bolton is like a Chatty Cathy doll that only says "Bomb them! Attack!"
As Trump put it in 2020: "If I listened to him, we would be in World War Six by now."
But Trump also understood how to use Bolton strategically. "When I hired him, he served a good purpose," Trump said recently. "I'd walk into a room with him in a foreign country, and the foreign country would give me everything because they said, 'Oh no, they're going to get blown up because John Bolton's there.'"
Bolton on Trump
Bolton was equally unsparing. "I don't think he's fit for office," he said in 2020. "I don't think he has the competence to carry out the job."
In his memoir, Bolton wrote that Trump "believed he could run the Executive Branch and establish national-security policies on instinct, relying on personal relationships with foreign leaders, and with made-for-television showmanship always top of mind."
He observed that Trump "couldn't tell the difference between his personal interests and the country's interests."
But Bolton's critique says more about his own rigid worldview than Trump's approach. What Bolton describes as incompetence is actually a common business management style — quick decisions based on instinct and relationships rather than endless analysis. Bolton can't fathom that there might be more than one way to lead effectively.
Bolton also claimed that Putin "played" Trump and that Trump simply "listened to the last person in the room." Both criticisms assume Trump operates without any coherent strategy or core beliefs — which says more about Bolton's dismissive view of Trump than it does about Trump's actual decision-making process.
As I discussed in my op-ed "The Fool's Mask," these characterizations misunderstand Trump's deliberate performance that often is meant to conceal and misdirect and not so trite as Bolton thought.
Under-Planning vs. Over-Planning
Their partnership was doomed by two opposite but equally limiting instincts:
Trump under-plans. He's the one-minute manager — agile, flexible, and fast — but execution often collapses when the details don't sort themselves out.
Even in business, Trump often doesn't plan or think things through sufficiently, which is why he had so many failed businesses and bankruptcies: Trump Taj Mahal (1991), Trump Plaza Hotel and Casino (1992), Plaza Hotel (1992), Trump Castle Hotel and Casino (1992), Trump Hotels and Casino Resorts (2004), and Trump Entertainment Resorts (2009). Plus failures like Trump Steaks, Trump Airlines, Trump Vodka, Trump Mortgage, Trump University, Trump Magazine, and Trump Ice.
Diplomacy and world politics is complicated and you can't always walk things back.
But I think Trump's idea is to work from the top down.
Bolton over-plans. He drowns every problem in strategy memos and rigid frameworks — but no matter how detailed the analysis, every flowchart ends in the same box: bomb them.
It was improvisation versus doctrine, and neither man trusted the other's map of the world.
The Breakup
The Trump–Bolton experiment was never built to last.