An author who has written extensively about Donald Trump revealed on Tuesday that the president’s latest ploy to win the 2026 midterm election has unsettled White House insiders, and even the president is acknowledging that it is “going wrong.”
Michael Wolff, who has written four books about Trump, said during a podcast interview on Tuesday that Trump is trying to find an issue that will take up as much media airspace as possible to have a shot at competing with Democrats in the midterm. Currently, the president is polling poorly on a range of issues that are shaping up to dominate the next election, from affordability to the economy.
Trump’s efforts to arrest Venezuelan dictator Nicolás Maduro and his threats to invade Greenland are part of that strategy, Wolff said. However, it appears that the strategy is going wrong, he added.
“He has a sense that this is going wrong,” Wolff said. “That they could lose the House and then even acknowledging the possibility that they could lose the Senate, which he says, ‘Then I’m back in court, [and it] won’t be pretty.’”
“This started to happen earlier in the fall when this whole kind of conversation started to go on, and that ‘We’ll have one year.’ So he said we’re going to have to go for Greenland,” he continued. “Now, when he said this, everybody regarded this as a joke … and then people who were slightly more worried than that kind of quiz, Susie Wiles, and she just kind of rolled her eyes and kind of refused to even entertain the possibility of Greenland.”
Wolff noted that Defense Secretary Pete Hegseth’s reemergence in the administration is another sign that Trump is still looking for an issue to take up airspace. Hegseth was largely sidelined by the administration earlier this year after the Signalgate scandal broke. But he has increasingly found himself back in the fold after the boat strikes, Wolff said.
“So he sort of announced we need something for 2026, a standout thing for 2026,” Wolff continued. “It has to be a whole new big deal. He’s been going around and saying it has to play. It has to play.”
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