Even a Broken Clock Is Right Twice a Day: Would Putin Have Invaded Ukraine If Trump Were President?
This essay is not a defense of Donald Trump. It's not a critique of his presidency or a judgment on his worldview.
It's a focused answer to one specific question:
Would Vladimir Putin have invaded Ukraine while Trump was still in office?
I believe the answer is no.
And I believe the timeline, behavior, and signaling—on both sides—support that view.
🕰️ This Was No Pearl Harbor
The invasion of Ukraine in February 2022 was not a surprise. It wasn't a bolt from the blue. It wasn't Pearl Harbor.
It was a year-long military buildup carried out in full view of the world:
Covert Intelligence:
War planning probably detected from the beginning of the Biden presidency
Strategic decision-making likely intercepted at the highest levels
Initial resource allocation and military preparations probably tracked
Communications likely showing invasion timeline development
Open Intelligence:
Satellite photos of troop movements
Intelligence briefings to Congress and allies
Open-source footage on social media
Kremlin speeches telegraphing intentions
Visible Military Buildup:
Tank formations massing at the border
Artillery units in assault positions
Fuel convoys and supply lines
Field hospitals - the telltale sign of planned casualties
This wasn't a military exercise or war games. Covert intelligence probably knew about invasion planning from the very beginning of the Biden presidency, a year before the visible buildup that the rest of the world started to see. The Biden election was likely seen as a strategic opportunity.
Putin didn't just fail to hide his plans—he advertised them. You could watch it on the nightly news. You didn't have to be in the CIA to see what was going on.
🛠️ What the West Could Have Done—But Didn't
Armed with that intelligence—and that open visibility—the West had choices. Real ones. Timely ones.
The U.S. and Europe could have:
Moved lethal aid into Ukraine early
Conducted joint NATO-Ukraine military drills
Deployed American or European advisors in-country
Announced financial and energy sanctions up front—not as after-the-fact punishment
Applied real political pressure on Nord Stream 2
Created ambiguity instead of signaling inaction
Instead, Western leaders responded with public restraint: "We will not send troops."
"We don't want to provoke Russia."
"Sanctions will come after an invasion."
Putin didn't need spies or backchannels. He got the message—loud, clear, and repeatedly.
That wasn't deterrence. That was a green light.
🛑 Biden Froze Like a Deer in Headlights
During Trump's presidency, the U.S. broke with Obama-era policy and delivered lethal military aid to Ukraine—Javelin anti-tank missiles, training, and logistics. This wasn't symbolic—it changed Ukraine's ability to defend itself.
When Biden took office, his administration paused a military aid package and initially withheld additional lethal weapons—reportedly to avoid "provoking Russia."
This mirrored a broader pattern. As I pointed out in my critique of Obama on the world stage in "A Sobering View of the Obama Administration Part I"—and you can skip reading it if you want, just know that it was piss poor—the U.S. under his leadership failed to project decisive military clarity when it mattered. Biden's response here was no better. The same caution returned, and with it, strategic resolve vanished at exactly the wrong moment.
Only months later, when it did not act as a deterrent, did Biden resume arms shipments. But by then, the message was already clear:
The U.S. had stepped back.
And Putin stepped in.
🔁 Trump's Response Would've Been Different
No one can say exactly what Trump would have done.
He might have:
Bluffed publicly
Threatened Putin directly
Tried to make a de-escalation deal
Declared Ukraine a neutral buffer
Or done something theatrical to muddy Putin's timing
I can't imagine Trump waiting for at least one year, and most likely two, doing nothing while realizing what was going to happen. He did not want a war starting during his presidency.
Whatever action he took, it would have forced Putin to recalculate. And uncertainty alone might have been enough to derail the invasion.
Now the war presents a much more complicated problem. The cat is already out of the bag and Putin has too much invested to go home. Trump's recent attempts to end the conflict show he doesn't quite know what to do with a war already in progress. But when it really matters—in moments of pressure and decision—Trump tends to act.
🎭 Unpredictability as Deterrence
Putin operates with cold calculation. He tests boundaries when he believes he understands the risks. With Biden, those boundaries were clearly marked: no troops, no escalation, no serious preemptive cost. Putin surely knew that Biden would do nothing.
With Trump, it was different. Putin would have had no real idea what Trump would do.
If you watch players in Vegas play hold'em, you know as a viewer what's in their hand, but it's amazing how bluff and strategy separate the winners from the losers. Even with partial information about your opponent, uncertainty about their next move changes how you play. You never see winning players announce "I always fold pocket pairs" or "I don't bluff when I'm scared." Predictability is how you lose.
And this wasn't just theoretical. Trump's unpredictable behavior had previously rattled the Kremlin—most notably when he ordered a sudden missile strike on Syria in 2017, and when he later authorized the assassination of Iranian General Qasem Soleimani, who had been directing regional operations from Syria and Iraq. These actions were abrupt, dramatic, and not clearly telegraphed in advance.
Putin was playing against someone who might fold with a great hand or go all-in with nothing. That uncertainty alone changes how you play, regardless of what cards you think they're holding.
🎖️ Lt. General Ben Hodges Observations: From Buildup to Now
Retired Lt. General Ben Hodges has been one of the most vocal critics of Western strategic communication failures during the Ukraine war. He's pointed out the stupidity of constantly telling Russia what the West will not do.
Western leaders responded with public restraint that became a roadmap for Putin:
No troops
No escalation
No preemptive strikes
No red lines
No whatever
As Hodges puts it: "We're with Ukraine for as long as it takes." What a totally empty statement! That means nothing. As long as what takes?
Hodges argues the West failed to define its objective: "My president has got to say: 'We want Ukraine to win. We want Ukraine to eject Russia back to the 1991 borders.'" That's what should have been said from the beginning.
It didn't signal weakness. It showed their hand. When you play poker, you don't tell your opponent what's in your hand and what your betting strategy will be.
Hodges has been blunt about the consequences: "Right now, Putin sees that we are not committed to Ukraine winning. So he just has to hang on."
Western leaders undermined their own position by obsessing over nuclear threats. They probably did this because they were terrified Putin might start a nuclear war and wanted him to know what they were not going to do - hoping to prevent miscalculation and keep things from spiraling out of control.
But as Hodges notes, "There's zero benefit to Russia if they use a nuclear weapon" and "Russia, as terrible as they are, does not want to commit suicide."
The fear of nuclear weapons became more paralyzing than the weapons themselves. As Hodges puts it: "Their weapons are only useful when they threaten it, because they can see how many of us are terrified that they might actually do it."
🧩 A John Bolton Observation
John Bolton, who served under Trump and later broke with him publicly, has said Trump has no consistent strategy, no policy discipline, and often believes whatever the last person in the room tells him.
While Bolton is consistently critical of Trump's unpredictability, calling it chaotic and undisciplined, he inadvertently makes the case for why it worked as deterrence. That kind of unpredictability is exactly what's hard for adversaries to plan around.
Even Bolton—despite his disdain—admits the one thing that matters: Putin didn't invade while Trump was in office.
🎯 A Nod to Trump
I'm not a fan of Donald Trump. We can leave that understatement without further discussion.
But the guy has a lifetime of experience negotiating and playing mental poker with high level opponents in business. He's not a complete idiot.
This kind of situation is coming right into his power alley (the place in baseball that you don't want to pitch to a particular batter unless you want to see them knock it out of the park).
🎯 Final Thought
Trump was in office.
Putin waited.
The invasion didn't happen.
Even a broken clock is right twice a day.
This might just have been one of them.