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Tired of winning? Good, because Trump is losing in Ukraine.

During the 2016 presidential campaign and again in the 2024 campaign, then-candidate Donald Trump repeatedly told the American public they would win so much, they would be “sick and tired of winning.” 

Who would have thought America would have become “tired of winning” so early in Trump’s second term? 

It certainly seems that way when it comes to the U.S. supporting a winning plan in Ukraine. Russia is dictating the terms, while the Trump administration appears to be obliging in order to get a deal done. Team Trump is dangerously out of sync and desperately needs a reset or it risks getting played by Russian President Vladimir Putin.

One month into Trump’s second term, his administration has already “bent the knee” to Putin on three key demands: NATO membership, Ukrainian President Volodymyr Zelensky’s legitimacy and presence during negotiations, and the retention of the four illegally and partially occupied annexed oblasts in September 2022 — Donetsk, Luhansk, Zaporizhzhia and Kherson — and Crimea in March 2014. 

And negotiations have not even begun in earnest yet. That is not winning — that is capitulation, also known as losing.

As we warned might happen last week, Team Trump appears to have become lost in a “fog” of its own making. Troubling ill-advised concessions, as a result, inexplicably became an overarching White House mindset.

Defense Secretary Pete Hegseth told the Ukraine Defense Contact Group on February 12 in Brussels, “We must start by recognizing that returning to Ukraine’s pre-2014 borders is an unrealistic objective. … The U.S. does not believe that NATO membership for Ukraine is a realistic outcome of a negotiated settlement. … There will not be U.S. troops deployed to Ukraine.”

Keith Kellogg, Trump’s envoy for Ukraine, doubled down on Hegseth’s “unrealistic objective” comment by adding, “I think there will be a certain agreement on the potential loss of territory.” It was as if the Trump administration were negotiating with itself.

Putin was already sensing blood in the water. During a January 28 interview with state TV channel Rossiya 1, he reiterated his claim that Zelensky is “illegitimate” and said that he has no right to sign any documents in potential peace negotiations. The Russian president continued saying, “Negotiations can be held with anyone, but due to [Zelensky’s] illegitimacy he has no right to sign anything.”

Then on February 15, sensing weakness in Washington, Moscow hammered it home during a TASS interview with the pro-Putin former Ukrainian parliamentarian Viktor Medvedchuk to reiterate the Kremlin’s false narrative about Zelensky’s illegitimacy. The next day, Kremlin spokesman Dmitry Peskov doubled down on that message, saying, “Ukraine thus lacks sovereignty.”

Secretary of State Marco Rubio, along with National Security Adviser Michael Waltz and U.S. Envoy to the Middle East Steve Witkoff, began bilateral meetings with their Russian counterparts, consisting of Foreign Minister Sergei Lavrov and Russian Aide to the President Yuri Ushakov, in Riyadh, Saudi Arabia, on Tuesday. The goal is to end the war in Ukraine. Absent, however, were Kellogg, Zelensky, European leaders and NATO

It is hard to have negotiations to end a war when the country invaded, and the NATO alliance supporting its defense, are not represented at the table. Zelensky told NBC’s “Meet the Press” on Sunday that he “will never accept any decisions between the U.S. and Russia about Ukraine” if Ukraine does not participate in those negotiations.

Granted, this was just the opening round — a condition setter for future discussions. But the negotiations cannot solely be about what is in America’s best interest. That is is the perception, and Rubio’s comment that “the U.S. will be ready to engage Kyiv and European partners in the settlement process at later stages” only strengthens that narrative.

Dictating terms to your allies is a bad look. Team Trump should have learned that lesson from the Biden administration’s dealings with Ukraine and Israel.

Dictating elections in Ukraine after a peace agreement is signed should be a non-starter. That would only validate Russian allegations that the Ukrainian government is illegitimate.

How would the U.S. guarantee Russia will not try to influence the election to emplace pro-Russia government? One need only look at recent elections in Moldova and Georgia — and arguably the U.S. — to understand this threat.

Russia sought additional concessions during their initial meeting. Lavrov told the American delegation that “Moscow would not accept the deployment of NATO troops in Ukraine, whatever flag they were under.” He also said there was “high interest” in lifting economic barriers between the U.S. and Russia.

Given all of the above, it certainly seems Team Trump is capitulating to Putin’s negotiation demands. Putin is setting conditions to win; Team Trump is in a rush to bring the war to a conclusion and “stop the killing,” whatever the cost.

But the strategic cost would be high. The U.S. is a founding member of NATO — a defensive alliance formed to deter Russian aggression in Europe. Trump’s “America First” mantra does not mean NATO, Ukraine and Europe second. In terms of national security, the two go together.

It was Gen. George Patton who told us that “Americans love a winner and will not tolerate a loser. Americans play to win all the time.” Team Trump is on the path to losing in Ukraine. The end state cannot be the easy wrong — in this case, throwing Ukraine and Europe under the bus to stop the war — versus the difficult right, enabling Ukraine to win the war.

Nor does Trump have any business blaming NATO or Ukraine for the war in the first place, as he did Tuesday evening. That is not winning. That is loser behavior, to borrow from the president’s own vocabulary.

There has never been a plan to win the war in Ukraine — not under the Biden administration, not drafted by NATO and not by the Trump administration. Throwing money, weapons and ammunition at the problem without a plan has only prolonged a war that Ukraine could still win. 

Putin is at his absolute weakest, yet Team Trump forges ahead with peace plans that benefit only Russia and threaten the long-term security of Ukraine and Europe. 

The war may stop, but the killing will continue. Russia will erase the Ukrainian identity by a different means.

Col. (Ret.) Jonathan Sweet served 30 years as an Army military intelligence officer. Mark Toth writes on national security and foreign policy.



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