Facing Trump are two immediate challenges that would vex any president: ending the war in Ukraine while deterring more Russian aggression, and bringing hostages home from Gaza without sparking a new round of fighting between Israel and Hamas.

Trump has readily tested his diplomatic mettle in each case, deploying a trademark mix of pressure and praise to convince parties of the need for negotiations.

Senior U.S. officials will sit with Ukrainian counterparts in Saudi Arabia next week, just days after Trump paused military aid to Kyiv and demanded Ukrainian President Volodymyr Zelensky apologize for a rancorous Oval Office meeting. Hamas, meanwhile, must decide whether to release all of its hostages after Trump’s threats of military action, a gambit that upended sputtering talks between Israel and the terrorist group.

National Security Council spokesman Brian Hughes insists Trump’s past record in the White House speaks for itself, pointing to the Abraham Accords and the defeat of Islamic State, as well as the maximum pressure campaign against Iran. Trump, even before his inauguration, helped the Biden administration strike the cease-fire between Israel and Hamas.

Hughes added that Russia didn’t invade a neighbor on Trump’s watch, though Moscow’s war in eastern Ukraine, which started in 2014, continued throughout his prior tenure in the White House.

But Trump’s first term also demonstrated some of the limits of high-stakes public diplomacy. His warnings of an impending nuclear holocaust led to three meetings with North Korean leader Kim Jong Un but failed to lead to any agreement to dismantle Pyongyang’s weapons program.

He struck a deal with the Taliban to end U.S. involvement in the Afghanistan war, but left the withdrawal—and the chaotic collapse of the Western-backed government in Kabul—to his successor, then-President Joe Biden.

And Trump tore up the nuclear accord limiting Iran’s path to the bomb, pursuing instead his maximum pressure policy meant to deprive Tehran of funds needed to pursue an aggressive military policy. The result, however, is that Iran has moved closer to having the ability to start a nuclear weapons program.

Iran’s supreme leader, Ayatollah Ali Khamenei, in Tehran last month, at a meeting of defense industry experts and scientists. Photo: Iranian Supreme Leader’s Office/AFP/Getty Images

Even Trump’s most celebrated, hard-won pact had its limits. The Abraham Accords, which normalized ties between Israel and Arab states after years of enmity, sidelined the Israeli-Palestinian conflict. Now, efforts to get Saudi Arabia to join those countries in establishing formal relations with Israel have stalled amid the continuing Gaza conflict.

Trump nonetheless is forging ahead with Middle East dealmaking. On Friday, he revealed that he sent a letter to Iran’s leader to revive nuclear talks. His entreaty to Tehran has been met with immediate skepticism, and Abbas Araghchi, Iran’s foreign minister, said Friday Iran wouldn’t engage in nuclear talks with the U.S. until Trump reversed its sanctions campaign on the Islamic Republic.

At the same time, Trump’s attempts to speak nicely about Vladimir Putin while bullying Zelensky—so that both nations come to the table—appeared in part to backfire. Russia, seizing on the pause of U.S. military support for Ukraine, launched large-scale attacks on Ukraine’s energy infrastructure Thursday night and early Friday morning.

In response, Trump posted on social media Friday that he would impose tariffs and sanctions on Russia until a cease-fire and “FINAL SETTLEMENT AGREEMENT ON PEACE IS REACHED.”

But later in the Oval Office, Trump said he still believed Russia wanted a peace deal despite the bombing campaign, and that the real impediment to peace was Kyiv. “And Ukraine, I’m finding it more difficult, frankly, to deal with Ukraine,” he said. “I don’t know that they want to settle. If they don’t want to settle, we’re out of there.”

The U.S.-Ukraine talks will take place in Saudi Arabia despite no clear pathway toward protecting Kyiv against Putin’s aggressions long-term. Trump has refused to back a European plan to deploy peacekeepers to Ukraine until after a cease-fire, while Russia has repeatedly rejected the prospect of foreign forces there. Zelensky insists he wants to sign a peace deal but only under the right conditions.

Ukraine is open to signing a deal giving U.S. companies access to its rare-earth minerals, which could potentially keep Trump interested in the country’s security long term. “This deal today gives Ukraine the chance to survive,” Andrzej Duda, Poland’s president, said in an interview.

Other European officials are aghast that the Trump administration doesn’t seem to have a plan for what follows a sit-down meeting. One senior European official said closed-door conversations about Ukraine involve little more than U.S. counterparts assuring allies that Trump is the ultimate dealmaker, and there appears to be no discernible strategic planning beyond that.

He faces a different challenge in Gaza, where the U.S. this week escalated the threat against Hamas after attempts to engage directly with the group failed to yield results. Trump had dispatched his hostage envoy, Adam Boehler, to speak directly with Hamas, a move that sidelined mediators Qatar and Egypt and could encourage the terrorist group to expect one-on-one talks going forward

Steve Witkoff, Trump’s Middle East envoy, on Thursday told reporters, “I think there’s going to be some action taken” if Hamas fails to surrender its hostages. “It could be jointly with the Israelis.”

Asked shortly afterward if Witkoff meant the U.S. would join Israel in a military action, Trump said Thursday, “Well, we’re going to find out.”

A temporary cease-fire between Israel and Hamas expired last weekend, complicating the U.S. task of brokering a permanent peace with commensurate hostage releases. Israel blocked humanitarian aid to Gaza after Hamas rejected its proposal to extend the cease-fire without a commitment to end the war or fully withdraw its troops.

The president’s supporters say he has proved himself adept at getting people to the table. “His negotiating style is to make threats and extreme demands to throw the other side off balance and bring them to the table eager to make a deal,” said Matthew Kroenig, director of the Atlantic Council’s Scowcroft Center for Strategy and Security. “That is the playbook he is now following in both Ukraine and Gaza.”

The real question, however, is whether just getting people to the table, and even striking a deal, makes for effective diplomacy, at least in the case of Ukraine.

“We may have made a deal more likely by dramatically worsening Kyiv’s alternatives, but will that deal actually advance U.S. goals?” said Michael Singh, a senior National Security Council official in the second Bush administration. “That’s far less clear, but crucial.”