Trump’s ‘art of the deadline’ flaunts his dealmaking prowess

Call it the “Art of the Deadline.”

President Trump has in his first few weeks of his second term shown a tendency to set a deadline for a foreign leader, give himself an opening to shift the deadline, then declare victory when he’s able to extract something of value.

Trump did it when he first told Canada and Mexico they’d be hit with tariffs on Inauguration Day, only to move the deadline back to Feb. 1. When he readied tariffs that day, he was able to tout concessions on border enforcement and pushed the deadline back a month.

The president this week threatened Hamas with a Saturday deadline to release all remaining hostages in Gaza. He gave himself a bit of wiggle room, saying Israel could choose to overrule him. But the mere threat allows Trump to put himself in a stronger position and potentially gain something.

“He’s using deadlines to force people’s hands,” one Trump ally told The Hill. “This threat of deadlines is a way for Trump to close the gap timewise on a better negotiation for the U.S.”

Trump has long used bellicose rhetoric and the threat of action to coax reaction out of rivals and bring them to the table. But he has especially relied on that in the months since he won a second term.

The tactic has not always been fully successful, but it has allowed Trump to move the goalposts when needed and declare victory when he’s able to get concessions.

He threatened in early January that “all hell will break out in the Middle East” if Hamas did not release all hostages by Inauguration Day. While all hostages were not released by Jan. 20, Hamas and Israel did strike a ceasefire agreement that allowed for some hostages to be freed in the weeks after.

Trump, unsatisfied with the pace of hostage releases, again threatened this week that Hamas would face consequences if it did not free more prisoners by Saturday at noon.

“I personally think Hamas will not meet the deadline. They are trying to play the tough guy but we’ll see who is the tough guy here,” Trump said Tuesday.

Trump similarly said he intended to impose tariffs on Canada and Mexico for weeks leading up to Inauguration Day. He later set a Feb. 1 deadline for imposing those tariffs. When Trump signed off on the tariffs on Feb. 1, the fine print stipulated they would take effect on Feb. 4.

That extra wiggle room allowed Trump to hold last-minute calls with the leaders of both Canada and Mexico, who separately committed to take additional steps to crack down on the flow of illegal drugs at the border. Now, the deadline for tariffs is in early March.

To skeptics, Trump’s shifting deadlines are a sign that he is merely using them as a negotiating tactic and they don’t have to be taken all that seriously. They are flexible, so long as Trump can tout something of value in the meantime.

But to Trump’s allies, the use of deadlines, even when they are flexible, are just another sign of his deal-making prowess.

“He’s the master of the art of the deal. He is America’s dealmaker in chief,” White House press secretary Karoline Leavitt said Wednesday. “He leads from a position of securing peace through strength. And I think time and time again already in just four weeks, we have seen the president being able to negotiate successful deals with our partners, our adversaries all around this world.”

‘Elon Musk Derangement System’ takes hold

Move over, “Trump Derangement System.” The president’s circle sees a new affliction taking hold of Democrats, and it’s one that could be politically useful: “Elon Musk Derangement Syndrome.”

“EMDS might be more powerful than TDS in terms of living rent free in Democrats’ heads,” the Trump ally told The Hill.

The billionaire, top ally to the president and head of the administration’s efforts to shrink the government has become a point of fixation for Trump’s opponents. It’s no longer Trump’s every move that alarms and irritates Democrats, but Musk’s as he builds extraordinary influence and power within the White House.

Democrats have taken to describing Musk as the true president and the one calling the shots. Democratic lawmakers spent most of Wednesday’s first subcommittee hearing on Delivering on Government Efficiency attacking Musk. Rep. Robert Garcia (D-Calif.) pulled out a photo of Musk, describing it as a “d‑‑‑ pic.”

Musk himself has acknowledged he’s a lightning rod for controversy and attacks.

“What? I have detractors?” Musk asked sarcastically when a reporter on Tuesday sought to ask about what critics have said.

But the attacks on Musk stand to benefit Trump, according to some of his advisers and supporters. It gives Trump distance from certain controversies, and it forces Democrats to defend certain spending that many Americans may view as unnecessary.

“It’s a political weapon for Trump, because it forces Democrats to defend the indefensible,” said Ford O’Connell, a Republican strategist.

What to makes of Trump’s comments on Vance

The Beltway took notice when Trump told Fox News anchor Bret Baier during a pre-Super Bowl interview that it was “too early” to anoint Vice President Vance as his successor looking ahead to 2028.

“No, but he’s very capable,” Trump said. “I think you have a lot of very capable people. So far, I think he’s doing a very fantastic job. It’s too early, we’re just starting.”

Much has been made of Vance’s place in the administration in the early weeks, particularly because of Musk’s high visibility. 

Sources close to the White House said Vance has a strong relationship with Trump. They also cited Trump tasking him with navigating the future of TikTok and with meeting with Ukrainian President Volodymyr Zelensky this week as a sign he’s being trusted with big issues.

Some Trump allies also downplayed Trump’s comments to Fox News, comparing it to last year when he turned his running mate selection into a Beltway version of “The Apprentice.”

“There’s no way he’s going to say who he’s going to pick, because he wants everyone to work on his agenda as hard as possible so they can be the person picked,” one Trump adviser told The Hill. “At the same time, though, if we were going to say as of today who’s the favorite it’s absolutely JD.”