Trump wants deals on Ukraine and Israel. Here’s why he will struggle.

Donald Trump may be at war with Washington but he’s still eager to make peace with the rest of the world.

The incoming 47th president is stocking his Cabinet with super-hawks and mega-disrupters who, in the eyes of Trump’s critics, threaten to immolate the entire federal government. Yet some officials who know him say Trump the agitator is still Trump of the “Art of the Deal” — the self-styled master negotiator who sought to cut deals with U.S. adversaries around the globe when he was president last time and wants to do it again.

“I told the president very early in my tenure, ‘You’re going to be known as the peacemaker,’” Robert O’Brien, who was Trump’s last national security adviser in his first term and has been deemed a top contender for a senior role in the new administration, said in an interview. “I think that is still his vision.”

The problem: Even in his first term, Trump failed in his efforts to achieve successful agreements with China, Iran and North Korea. And in the four years since he left the Oval Office, the world has moved on, changing in ways that mean he faces a much harsher international environment than last time — an environment that makes it unlikely that even the wars in Ukraine and the Mideast, which have exhausted all sides, will end anytime soon.

Here are five ways conditions have changed globally that all but ensure Trump is going to find it harder to get his way this time around.

1. Russia Is Escalating the War in Ukraine

Trump already faces the prospect of breaking one of his biggest campaign promises, having repeatedly pledged to end that war “before I even become president.” Over the summer he said he’d do it “in 24 hours,” presumably by declaring a cease-fire on the current front lines and then striking a deal in which Ukraine gives up some territory — and future NATO membership — in return for peace.

But any such deal requires the front lines to be somewhat stable, and in a phone call two days after the election, Trump reportedly warned Vladimir Putin not to escalate his 2½-year-old invasion. The Russian president has, instead, done the opposite: He is still massing forces in Ukraine’s southeast in apparent preparation for a new offensive, and over the past week Putin has launched some of his biggest missile attacks on Ukraine in months.

Ukraine, meanwhile, is running out of troops. This week, President Joe Biden sought to give Kyiv more leverage before he leaves office by supplying the Ukrainians with long-range missiles. Ukraine promptly used them to attack Russia, which responded by threatening, yet again, nuclear war. Biden’s move led Trump’s incoming national security adviser, Michael Waltz, to comment: “This is another step up the escalation ladder, and no one knows where this is going.”

True, this would seem to be Trump’s moment: On the stump he repeatedly said the greatest danger America faced was “World War III” and only he could prevent it, and Putin has indicated he’s willing to discuss a cease-fire. But neither Putin nor the Ukrainians are playing along for now. The GOP, meanwhile, is still heavily populated with fairly strong supporters of Ukraine, including Trump’s incoming secretary of State, Sen. Marco Rubio. If they have his ear, Trump may be loath to begin his presidency with a display of weakness by simply surrendering large parts of Ukraine to Putin.

2. Israel’s Threats of Annexation Could Prolong Hostilities

When it comes to Israel’s two-front war in Gaza and Lebanon, the president-elect has indicated to both Israeli Prime Minister Benjamin Netanyahu and senior negotiators in Qatar that he supports Netanyahu’s military plans but wants to see him “wrap things up” by the time Trump is inaugurated on Jan. 20, 2025.

But while Netanyahu is expected to be more willing to bend to Trump than he has been with Biden, the Israeli leader is also in a stronger position politically — and more able to resist U.S. pressure — than he has been since the Oct. 7, 2023 attacks by Hamas. Following Israel’s successful campaigns against Hezbollah and Hamas, Netanyahu has strengthened support in his cabinet and made it likely he can survive in power for at least another year.

True, the Israeli Defense Forces have been saying for some time that its military objectives in Gaza have been met, and the Washington Post reported recently that Israel is preparing a cease-fire deal with Hezbollah in Lebanon as a “gift” to Trump when he takes office in January.

But Netanyahu said a week later that Israel will continue to operate militarily against Hezbollah in spite of any cease-fire. And Netanyahu’s government is openly discussing annexation of the West Bank. That might win support from the pro-Israel hawks on Trump’s team — including Rubio, U.N. Ambassador-designate Elise Stefanik, and Israel Ambassador-designate Mike Huckabee — but it would also almost certainly prolong hostilities and indefinitely delay a proposed Saudi-Israeli normalization pact that is seen as the crux of a broader peace deal in the region.

3. Iran Is Much Closer to Going Nuclear

Trump also faces new obstacles in fulfilling another campaign pledge: Getting Iran to surrender its nuclear weapons program. Trump plans to renew his “maximum pressure” campaign by dramatically increasing sanctions on Iran and choking off its oil sales, according to reports. And Iran’s relatively moderate new president, Masoud Pezeshkian, is showing a willingness to negotiate, saying, “Whether we like it or not, we will have to deal with the U.S. in the regional and international arenas.”

The problem for Trump is that Tehran is also newly motivated to go nuclear. In recent months, its conventional deterrence suffered a catastrophic failure against Israel, with the Israelis virtually wiping out the top leadership of its proxies, Hezbollah and Hamas, including conducting strikes inside Iran. Earlier this year, a senior Iranian Revolutionary Guards commander suggested Iran might review its “nuclear doctrine” in the face of the Israeli threats. And Iran is now far closer to a nuclear weapon than it was in 2018, when Trump repudiated the nuclear pact negotiated by his predecessor, Barack Obama.

What could also change Iranian calculations in favor of expediting their nuclear program is the confirmation by U.S. and Israeli officials that Israel’s retaliatory attack on Iran last month destroyed an active nuclear weapons research facility. Iran’s hard-liners have warned openly that such a degree of strategic vulnerability is unacceptable to them.

“We have the capability to build weapons and have no issue in this regard,” Kamal Kharrazi, an adviser to Iranian supreme leader Ayatollah Ali Khamenei, said on Nov. 1.

4. North Korea’s Kim Has a New Paramour: Putin

Nor can Trump count on any kind of disarmament deal with North Korea. In his first term Trump embarked on what he described as a “special friendship” with North Korean dictator Kim Jong Un, who reciprocated eagerly in a bizarre exchange of letters, calling their relationship “deep and special.”

But Kim has advanced his nuclear and ICBM program dramatically since Trump left the White House. Kim has also embraced a new military alignment with Russia that has rendered Pyongyang less reliant on U.S. assistance. The mutual defense agreement between Russia and North Korea, announced in June, means Kim is getting food aid, money and oil — and likely military technology — that previously only a deal with Washington could provide.

“We are not going to be able to get the agreement we were able to get in the first Trump administration,” said Stephen Wertheim, a foreign policy strategist at the Carnegie Endowment. “It’s going to take a lot more to pry North Korea away from the Russians.”

5. China’s Xi Has Become More Hard-Line

Trump will find it far more difficult to push China to play fair on trade and stand down on its threats to Taiwan, because Chinese President Xi Jinping is more of a hard-liner on all these issues than he was four years ago. Trump will also be forced to confront the fact that the deepening ideological partnership between Beijing and Moscow — one built on their mutual opposition to U.S. hegemony — does not lend itself well to his purely transactional, bilateral approach to geopolitics.

True, China’s economy is slowing dramatically, and Xi is relying partly on exports to revive it. Xi’s economic mismanagement has led to mounting debt, declining foreign investment and capital flight. Thus Trump’s threats to impose new 60 percent tariffs could hurt China badly.

But while Trump has all but promised a trade war with Beijing, he has also indicated he wants to avoid an actual shooting war over Taiwan. And that signal of softness on the Taiwan issue, along with Xi’s grand plan of turning China into a self-reliant global superpower, could make the Chinese leader even less willing to alter Beijing’s fundamental trade practices — including illegal subsidies to companies and widespread intellectual property theft — than he was last time Trump was in office. “It didn’t work the last time, and I see no reason why it would work this time,” said William Reinsch, a former U.S. Commerce undersecretary now at the Center for Strategic and International Studies.

The country’s ability to navigate these shifts will depend heavily on the personnel Trump brings in. Even under his iron rule, the GOP is undergoing an ideological battle between traditional hawks who seek to project strength abroad and are averse to negotiation, and on the other hand “restrainers” and “realists” who seek to avoid foreign conflicts, taking a more neo-isolationist, “America First” view. For now, it appears the hawks are being appointed to the most senior positions, including Rubio at State, Waltz as national security adviser and, most surprisingly, former Fox News host and combat veteran Pete Hegseth as Defense secretary.

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But there are countervailing forces already surfacing in the new administration who will be more inclined to counsel accommodation, especially when it comes to China. Trump has declined to appoint some longtime China hawks such as Arkansas Sen. Tom Cotton and his own former secretary of state, Mike Pompeo, who earlier this year said it was time to recognize Taiwan’s independence. Trump’s new inner circle includes several business people who might take a more diplomatic approach. Among them is his would-be adviser-in-chief, Elon Musk, whose success with Tesla manufacturing in China has depended on Beijing’s favor and who once described himself as “kind of pro-China.” Another is the co-chair of Trump’s campaign, Howard Lutnick, who has been nominated to serve as his Commerce secretary and who Trump said will “lead his tariff and trade agenda.” Lutnick’s Wall Street financial services firms, Cantor Fitzgerald and BGC Group, also have substantial business interests in China.

Other former Trump officials likely to gain senior roles in the new administration, such as former senior defense official Elbridge Colby, have blamed Taipei for being a security freeloader and implied that Trump wouldn’t be as quick to defend the island as Biden. As Trump himself said in a July interview with Bloomberg Businessweek: “Taiwan should pay us for defense. … Taiwan doesn’t give us anything.”

“These people believe we can’t risk sinking the Pacific fleet for a country [Taiwan] that doesn’t want to help itself,” said one national security expert who is close to the Trump transition. “So China policy could end up being more dovish than people think.”

The incoming president is already sending out peace feelers to foreign adversaries, even as he embarks on what can only be described as a hostile takeover of the federal government and a domestic war against the “deep state.” As Trump said at a Colorado rally in October, “the enemy from within” is “a bigger enemy than China and Russia.”

“I’m not going to start wars, I’m going to stop wars,” Trump declared in his victory speech the night of Nov. 5. In meetings with foreign delegations at Mar-a-Lago, Trump has said “he’s looking to end all of these conflicts,” even when it comes to Iran, although Tehran plotted to assassinate him, according to a diplomatic official briefed on one of those conversations. He noted that Trump himself started up a back-channel mediation with Iran after he ordered the Jan. 3, 2020, assassination of Iranian Gen. Qassem Soleimani. Musk met secretly with Iran’s U.N. ambassador after the election to defuse tensions, according to reports.

Gwenda Blair, author of the 2000 book The Trumps: Three Generations of Builders And A President, said for Trump the drive to leave a legacy as the great peacemaker is fundamental. “He would indeed like to be the dealmaker of the ages, using that same transactional DNA that propelled his grandfather during the Gold Rush, his father [building a housing empire] in the New Deal, and his own career in real estate, casinos and reality TV,” said Blair.

She warned, however, that “everyone else at the table is as self-interested as he is and far less vulnerable to lies, exaggerations, and distortions. In a global landscape of shrinking American hegemony, he may run aground on demanding a bigger slice for himself than they are willing to give.”

Trump might heed his own advice on this score. As he wrote in his 1987 book The Art of the Deal: “The worst thing you can possibly do in a deal is seem desperate to make it. That makes the other guy smell blood, and then you’re dead. The best thing you can do is deal from strength, and leverage is the biggest strength you can have.”

The very real question is whether Trump, in his pronounced eagerness to make deals, will have the leverage he thinks he needs. Without it, he may well find himself engaged in a series of one-sided negotiations in his second presidency in which he walks away, once again, empty-handed.