
I don’t have experience with international diplomacy, but I do have experience with difficult bosses. I recall when one such employer was presented with the company’s social media redesign. A man of President Trump’s generation (and no social media or design background), he began mercilessly picking our new Facebook page apart. His critique was mostly directed at the layout of Facebook itself, which, of course, our team couldn’t change. In such a situation, do you point out that your boss knows nothing about digital marketing? Or do you thank him for his input and agree that Facebook is poorly designed? Certainly, we’d all like to make our boss look foolish sometimes. But we also have livelihoods to maintain and mouths to feed. An experienced professional knows that you need to work around as well for your boss; to manage up as well as down. Otherwise, you won’t stay professionally experienced for very long.
Volodymyr Zelensky is a world leader, not an employee. But he’s also reliant on American support for his nation’s survival,1 and the US is now led by a cutthroat businessman. If I were the Ukrainian leader, I’d take a masterclass in managing up. I’d study my patron’s psychology and play to his vanity by praising him and criticizing his rivals.2 I’d wear a suit to the Oval Office, because I know my patron cares about appearances.3 In fact, I’d wear a red tie and a “Make Ukraine Great Again” hat, because I know he’s susceptible to visual flattery. I’d also make a series of largely symbolic political gestures to show that I’m on his side. For example:
Offer to conscript America’s illegal aliens into the Ukrainian army. Deportees could be given the option of fighting for Ukraine in exchange for EU residency rights. (Ukraine isn’t part of the EU, but the Europeans would surely agree.) This would help alleviate Ukraine’s manpower shortage, reduce America’s Venezuelan surplus, and provide a legal pathway to the First World for poor migrants to boot. The offer could even be extended to America’s convicted criminals to relieve overcrowded jails.4
Promise that, as the nation with the largest standing army in free Europe, Ukraine will support any American military ventures following peace with Russia. That could include sending troops to fight Mexican drug cartels and helping to seize and garrison the Panama Canal.5 Essentially, the Ukrainian army would become the US version of Russia’s Wagner Group, doing America’s dirty deeds abroad under a transparent cloak of deniability. In exchange, Ukraine would seek American backing for a European peacekeeping force.
Commit to investigating possible corruption by Hunter Biden during his time as a paid board member of Kyiv-based Burisma Holdings in 2014. President Joe Biden pardoned his son for all “offenses against the United States which he has committed or may have committed or taken part in during the period from January 1, 2014 through December 1, 2024.” But Hunter is not immune from prosecution for offenses against Ukraine, which could accordingly request his extradition.
Pledge to work with American companies, including the Trump Corporation and Jared Kushner’s Affinity Partners, to make Odesa the “Riviera of the Black Sea.” (Odesa is already sometimes called the “Riviera of the Black Sea,” but that’s a minor detail.) To symbolize the deal, Ukraine would erect a statue of Trump to replace the city’s dismantled monument to Empress Catherine the Great. American investment, backed by political muscle, could simultaneously help to secure freedom of navigation in the Black Sea.
It doesn’t matter if fewer than 100 illegals end up enlisting, the Ukrainian army proves ineffective at drug busting, the Hunter Biden investigation comes up empty, or the Trump Potemkin Hotel stays vacant. What matters is the image that such gestures help create. In the pre-Trump era, America supported Ukraine because the cause was noble. In the age of Trump, America will only support Ukraine if it’s seen as benefiting the US in general and/or Trump in particular. To an extent at least, Ukraine recognizes this new reality. After all, Kyiv first proposed a critical minerals deal during the Biden administration, but delayed signing so Trump could take credit. Still, Zelensky’s disastrous February 28 White House meeting shows that he has not fully adjusted to the new geopolitical bottom line.
A counterargument is that Zelensky was the victim of a planned ambush; that nothing he could’ve said (or worn) would’ve made a difference. Obviously, we don’t know for sure. But according to the New York Times,
three people with knowledge of what took place beforehand said neither Mr. Trump nor Mr. Vance had been looking to blow up a deal for Ukraine’s mineral rights, which Mr. Zelensky had been expected to sign in Washington. Instead, they said, Mr. Zelensky seemingly triggered the two American leaders by not sufficiently thanking the United States for trying to end the war (which Mr. Trump wanted to hear) and by pressing for commitments to protect Ukraine from Russian aggression going forward (which Mr. Trump did not want to hear).
The leaders had gotten along well enough before the cameras arrived. Only when journalists started asking questions—and Zelensky openly contradicted Trump’s position—did the meeting derail.6 The point is not whether Zelensky is right that Vladimir Putin is a bad actor. (He is.) The point is that a public spat isn’t worth the suspension of American military aid and intelligence sharing. Notably, Trump said he would continue to arm Ukraine earlier in that same meeting. Keeping his mouth shut and managing up might not have gotten Zelensky a security guarantee. But it wouldn’t have lost him the verbal commitment he already had. Even if Zelensky was, in fact, baited, he didn’t have to take the bait.
After Trump proposed relocating Gaza’s entire population to Jordan and Egypt, Jordan’s King Abdullah promised to accept 2000 Gazan children for medical treatment. Trump called Abdullah’s statement “beautiful” and “music to my ears,” even though that figure is around 0.1% of Gaza’s population. Critically, the king didn’t disapprove of Trump’s idea in front of him, instead saying “I have to look out for the best interests of my country” and dodging questions from reporters. More recently, Trump has said of his Gaza plan, “I’m not forcing it. I’m just going to sit back and recommend it.” When it comes to Ukraine, Trump is hardly standing on long-held principles. In 2017, his administration was the first to sell Ukraine lethal weaponry—which he even bragged about while arguing with Zelensky. True, Trump called Zelensky a dictator, but he also later joked, “Did I say that? I can’t believe I said that.” Are these the words of a man incapable of changing positions? The Ukrainian rallying cry is “Glory to Ukraine! Glory to the heroes!” But sometimes true heroes must trade uniforms for suits and idealism for realpolitik.
Europe is also a major supplier of aid to Ukraine, but Zelensky himself has said that his country has a “low chance” of survival without US backing.
Most Democrats will back Ukraine no matter what Zelensky says, so he could’ve scored an easy win by agreeing that Russia wouldn't have invaded under Trump’s watch.
As
writes:Zelensky has been wearing street clothes since the February 2022 invasion. Imagine him coming to the White House in a suit and dressing up for Trump after three years of not doing so for Biden or any other world leader. . . . the fact that Zelensky didn’t see that this was an easy way to ingratiate himself with Trump indicates that he has bad judgment and either doesn’t know how to manipulate the American president or is too proud to do so.
The precedent here is Salvadoran President Nayib Bukele, who offered to take in deportees of any nationality, plus American convicts, for a fee. The Trump administration praised the idea. And, of course, Russia has made ample use of convicts and foreigners (North Koreans) in its own war effort.
If the US requests assistance with an invasion of Greenland, Ukraine may have to sever its ties with Denmark. But realpolitik comes with a cost.
That Vice President JD Vance was the one to criticize Zelensky for being disrespectful is a classic example of office politics. Vance correctly anticipated his boss’s feelings and articulated them first to score points. In so doing, he also elevated his bid for the number-two spot on the org chart. (Though Elon Musk undoubtedly still holds the position.)
Admitting this feels like blaming Ukraine and/or Zelensky for the failure, but it also seems incredibly reasonable. It seems like a little bit of deference would have won Ukraine a lot more goodwill from the foreign power most capable of ending the war for Ukraine on the most advantageous terms. I have no doubt that Putin and the Russians pander to Trumps ego, calling his political comeback a masterstroke and just generally making him feel important.
I'm sure Putin just parrots back Trump's ideas while calling them very intelligent, making him feel that Trump has the leverage over Russia and Ukraine, while just doing whatever Russia wants on the ground in the meantime. It costs Russia nothing, weakens support for Ukraine, and generates even more conflict between the right and left in the US (by appealing to Trump, Trump says positive things publicly about Putin, which causes strong backlash from the left, and psychologically pushes Trump & Co. further towards defending their nominally pro-Russian position).
If Zelensky was just willing to call whatever Trump had to say genius, make loose concessions that had no significant practical costs in the long run (The mineral deal is so vague it would be very easy for Ukraine to pull out in 5-10 years *long after* US leverage forced a more favorable ceasefire for Ukraine). The half-trillion dollar deal is at least a 95% exaggeration (that's literally 2.5x Ukraine's GDP), but giving Trump the talking point "We made the greatest of deals with Ukraine. They gave us 500 BILLION dollars worth of resources. That's Billion with a B Folks. Never before has our Country made such a Great Deal. Do you think BIDEN could do that? I don't think so. Only I could do that Folks. And really, I think that Zelensky is a great guy. Smart guy. He respects the US so much. What did you say? Putin? He's a smart guy too, CUNNING. Smart but Cunning. We want to make a deal and end the war, and I think we can make a really great deal. Putin and Zelensky both know we can decide to make a deal. And we're going to make a great deal for the country. etc. etc." would go a very long way.
It's hard to assign blame to Zelensky since his country is being invaded, and taking a hardline emotional position in response to that is understandable, but at the same time you can't call it prudent.
Interesting piece. It made me think about how much of international reputation comes down not just to actions, but to how you package and sell those actions to the world.
A small example, if you ask people which countries fought alongside the US in the Korean War, Turkey almost always gets a mention, thanks to the legendary status of the Turkish Brigade. But Greece? Almost nobody remembers that Greek troops were there too, fighting under the same UN flag.
The difference isn’t what they did. Greek soldiers fought bravely, especially at Outpost Harry. It is rather how well each country managed the "story" of their involvement. Turkey actively cultivated the image of a fearless ally standing with the West, and it became part of their Cold War identity. Greece, on the other hand, treated its contribution more quietly, overshadowed by its own internal struggles after the Civil War.
The point being: what you do matters, but how you sell your story might matter even more. Something to keep in mind whenever we analyse the optics of leaders, speeches, and even fashion choices like Zelensky’s non-tie.