Trump May Find Out That Whining Does Not Always Lead to Winning

In an interview in 2016, then-candidate Donald Trump proclaimed, “I whine because I want to win, and I’m not happy about not winning, so I am a whiner, and I keep whining and whining until I win.” In his ten years in politics, the nation has seen ample evidence that here was one of those rare occasions in which Trump actually told the truth. What has come as something of a surprise—or perhaps not—is that Trump, sort of like the toddler he often seems to be, makes no distinction between the crucial and the petty. He needs to win them all and employs his whine-until-win strategy seemingly by reflex.

Whining doesn’t exist in a vacuum, however. With Trump, it goes hand in hand with bullying, the former only employed when the latter has failed. To Trump’s credit, he seems to have an acute sense of when to go from one to the other.

Until recently, he had employed the two with remarkable success. Not only did he bully and whine his way to winning two presidential elections, but he also succeeded in creating a rather large chorus of those who swore that he had won a third. After his re-election, he bullied and whined until terrified Republicans passed legislation that any fool could see would hurt their core supporters and damage their chances in the 2026 midterms.

But, although Trump would refuse to believe it, when bullying is no longer effective, whining can have diminishing returns. As his popularity plunged and a disaster midterm scenario took shape, a number of congressional Republicans, faced with potential Democratic majorities, decided they feared the electorate more than Trump. The Senate, in particular, started ignoring Trump’s bullying and turned a deaf ear to his whining. Republican Senators refused, among other acts of rebellion, to even call for a vote on the Save America Act.

But Trump knows no other tactic. For him, whining has occupied the space where, for others in politics, conciliation and compromise would be. Trump, born into great wealth and family power, has always been able to survive crises engendered by inflexibility by simply declaring bankruptcy of one sort or another—divorce, for example—and moving on. (Lying, the third prong of his pitchfork, has been liberally employed to explain away these retreats. Thus, TACO was born.)

Trump’s lack of adaptability should have been most problematic in his relations with the Supreme Court. Supreme Court justices do not have to stand for election and are therefore not susceptible to bullying. They can blithely ignore whining, as they have with most presidents of both parties. (Barack Obama’s confrontation with Samuel Alito at the State of the Union is a memorable example.) But the current Court is so political, so ideologically driven, that Trump might well have concluded they were as compliant as Congress had been.

Then came the decisions overturning Trump’s tariffs and his executive order on birthright citizenship. Even though virtually every other important decision had gone his way, Trump descended into fury, calling down the wrath of MAGA on justices…and their families…who had dared inflict him with two losses. Then, instead of realizing that just a soupçon of moderation could repair the damage, he has upped the stakes by challenging the Court to continue to dare defy him and the results could well set the tone for decisions the Court renders until the end of his term.

Refusing to be deterred from building a ridiculously overdone White House ballroom that no one really wants and the nation does not need, Trump has just asked the Supreme Court to grant an emergency petition setting aside an appeals court judgment that halted all above ground construction. Trump’s argument is that, after end-running an earlier series of orders that he cease construction, the project is now too far gone to stop. (This is a variation of the old Yiddish joke about the man who murders his parents and then throws himself on the mercy of the court on the grounds that he is an orphan.)

Although Trump might win this one, it is certain to leave a bad taste for John Roberts and likely Amy Coney Barrett as well. In addition to already asking the Court to overturn the pause on his executive order placing a nationwide ban on mail-in voting, sure to follow are emergency petitions on what are expected to be adverse decisions on Kennedy Center signage and the criminal prosecution of non-existent Reflecting Pool vandals.

But most significant in Trump’s new offensive is the appeal that appears the most petty—asking the justices to set aside the $83 million payment to E. Jean Carroll that was assessed after Trump continued to defame her after he lost a civil case in which a jury unanimously concluded that he had sexually assaulted her in Bergdorf Goodman in the mid-1990s.

After the original $5 million verdict in 2023, Trump was livid. He continued to deny ever meeting Carroll and claimed she was “not his type” although there was a photograph that showed them together and that he had confused her for his second wife. His mood did not improve when he was ordered to put the money in escrow pending appeal.

Trump responded by calling her a “whack job” on national television, adding “I think she’s sick, mentally sick.” While his appeals on the $5 million worked their way through the courts, Trump continued his insults.

But Carroll proved to be tougher than Trump gave her, and likely all women, credit for. She sued once more and this time she was awarded $83.3 million, including $65 million in punitive damages. Trump’s lawyers appealed on the grounds that presidential immunity should be applied because Trump made the statements while in office.

In September 2025, the 2nd Circuit Court of Appeals disagreed, rejecting both the immunity argument and that the award was excessive. “Given the unique and egregious facts of this case,” they wrote, “we conclude that the punitive damages award did not exceed the bounds of reasonableness.”

In late June, the Supreme Court, “without a noted dissent from the denial,” refused to hear Trump’s appeal to block the initial judgment and he was forced to pay Carroll $5.6 million, which included interest.

Having thus far failed to whine his way to victory, in July, Trump decided to give the Supreme Court one more chance. Instead of just paying the two dollars—pocket change; he is a billionaire after all—his lawyers asked the Court to review the larger judgment as well, using the same immunity argument that had failed in circuit court.

Key here is that it is this very panel of justices that expanded presidential immunity to encompass anything that can even vaguely be considered an official act, a decision for which they were widely upbraided and helped bring the Court’s approval rating to another record low. Now they were being asked to apply their new standard to protect a man who had been found to have committed sexual assault. They thus have the choice of limiting their first decision or being seen as protecting a sexual predator.

The justices will not be pleased with being forced to make this choice. Perhaps it will make no difference, but Trump’s overreach might well be on their minds during deliberations on the next case that seeks to expand presidential power.

Whining-to-win seems to have gotten tired with more than a few non-MAGA Republicans and perhaps now with two or even three Supreme Court justices as well.

We will find out in November whether voters feel the same way.