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Does Trump even care anymore that he’s losing?

Opinion

Does Trump even care anymore that he’s losing?

President Donald Trump arrives to deliver remarks on the economy in Clive, Iowa, on Jan. 27, 2026. (Brendan Smialowski/AFP via Getty Images/TCA)

(Brendan Smialowski/AFP via Getty Images/TCA)

Speaking at a rally in 2016, Donald Trump delivered these now-famous lines:

“We’re gonna win so much, you may even get tired of winning. And you’ll say, ‘Please, please. It’s too much winning. We can’t take it anymore, Mr. President, it’s too much.’ And I’ll say, ‘No, it isn’t. We have to keep winning. We have to win more!’ ”


Since then, he’s repeated a version of this cartoonish promise over and over again, only to be reminded of it by his opponents when he seems to be on the ropes.

But now, entering the second year of his second term, the wins have been increasingly hard to locate. Trump’s first attempt at winning — appointing Elon Musk to head up DOGE — was a chaotic, ineffective, and ultimately humiliating endeavor that saw the very public fracturing of their relationship.

The president’s signature economic initiative — tariffs — have done little to stimulate the economy and a lot to piss off our allies. His anti-crime and anti-immigration efforts, which initially had voters’ blessing and approval, have turned into deeply unpopular and divisive liabilities for both Trump and Republicans.

And if the last month has felt like a year to you and me, imagine how it has felt to Trump, whose losses are piling up on top of each other like a precarious and chaotic game of Jenga — and it’s poised to topple over. The question is, does he care?

There was Trump’s Greenland folly. Seemingly all-consumed with the bruising impact of losing the Nobel Peace Prize, he set his beady eyes north, attempting to muscle his way into owning the Danish territory with the surgical skill of an axe murderer and the diplomatic soft touch of the Kool-Aid Man.

After insisting America needed Greenland for national security, promising we would get it, and threatening to take it by force if necessary, Trump stormed Davos in hopes of leaving with the island as a souvenir. Instead, rebuffed by Europe and NATO, he was left announcing a vague (and possibly made up?) “framework” of a deal that has amounted to nothing so far.

In Minneapolis, where Trump deployed ICE in response to cases of Somali-American fraud schemes, the shooting deaths of two U.S. citizen protesters, mother of three Renee Good and VA nurse Alex Pretti, have sparked widespread outrage and condemnation.

While the administration and its supporters started out with a lot of tough talk in defense of ICE, often throwing the acronym “FAFO” around to justify violence against anyone who would get in their way, the tone has shifted considerably.

Controversial Border Patrol commander Gregory Bovino was moved off of Minneapolis, where DHS Secretary Kristi Noem was also leading the charge. Sen. Thom Tillis called for her ouster, and both Noem and Bovino will reportedly be replaced by Border Czar Tom Homan.

Numerous Republican lawmakers, aware of a looming midterm election, have come out to say enough is enough, and call for Trump to change course. Rep. Mike Lawler penned an op-ed in the New York Times saying what Trump has been doing “is not working,” acknowledging “Americans’ many legitimate concerns about how the government has conducted immigration policy,” and calling for the investigation of both deaths by law enforcement as well as Congress.

Right-wing media, too, has begun calling for a shift in strategy, with many on even Fox News ringing alarm bells.

There’s no other way to describe Trump’s results in Greenland and Minnesota as losses, ending with his retreat from a once emboldened position that no longer was tenable or politically prudent.

Undergirding both of those abject failures, of course, is Trump’s flailing economy. Trump’s approval rating on the economy, the issue most people care about the most, has swung a whopping 26 points in just a year, starting at plus-6 points to negative-20 now. Trump’s faring worse now than former President Joe Biden was at the same point.

Quite simply, Americans do not feel like this economy is working for them. That’s bolstered by reality, the impact of Trump’s dumb trade wars, but it’s also bolstered by perception, a belief that Trump is indifferent to the economic pain of his own voters and is focused on literally everything but affordability. That’s a dangerous combination in an election year.

It almost feels like Trump no longer cares. He’s running the country like a guy who was just told he has a year to live, checking off items on a bucket list. Only, instead of “skydiving,” it’s “depose a dictator,” “steal a peace prize,” and “invade a sovereign nation.”

He may not care, but Republican lawmakers definitely do. And they are tired of so much losing. Can they corral him back to the plot in time? The clock is ticking.

S.E. Cupp is the host of "S.E. Cupp Unfiltered" on CNN.


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