President Donald Trump hopes lightning will strike twice. Will it?

U.S. President Donald Trump’s recent success in the Middle East has emboldened the Trump administration to approach world conflicts in new ways.

Mr. Trump negotiated a cease-fire, hostage release, and peace accord during a flurry of diplomatic activity in recent months. Addressing the Israeli Knesset last week, Trump laid out a vision for the future.

And he was looking a lot further afield than the Middle East.

Calling the war in Ukraine, “A war that would’ve never happened if I were president” and “a shame,” Trump lamented that, “7,000 young soldiers a week are being killed.”

“More than that, this last week,” Trump told the Knesset. “It’s a shame. Should have never happened, but it did happen. And we won the race, and I took over this horrible war that’s been raging and I thought it would be easily settled. I thought it was a hell of a lot easier than doing what we just did very successfully with Israel and a lot of other people. But this came first and we’ll get that one.”

Mr. Trump expressed great faith in his envoy, Steve Witkoff.

“But I set up a meeting for him to meet with President Putin, thinking it would be a 15- or a 20-minute meeting,” Trump recalled. “Steve had no idea about Russia, had no idea about Putin, too much. Didn’t know too much about politics, wasn’t that interested. He was really good at real estate, but he had that quality that I was looking for, and I didn’t see it around in too many ways.”

“And I set up the meeting with Putin and I called. I said, ‘Is Steve finished yet?’ That was about a half an hour into the meeting,” Trump went on. “‘No sir, he is not. He’s still inside.’ This is in Moscow. I said, ‘Well, how’s he doing?’ ‘I don’t know, sir. He’s still inside.’ I called up an hour later. ‘Let me speak to Steve.’ ‘Sir, he’s still with Putin. He’s with President Putin.’ I said, ‘Wow, that’s a long meeting, one hour.’ I called up an hour later he was still with Putin. Three hours later he was still with Putin. Four hours later we started to get the word that he was gonna be coming out soon. And in five hours he came out.”

“I said, ‘What the hell were you talking about for five hours?’ And he says, ‘Just a lot of interesting things. We just were talking about a lot of interesting things,’ including what he went in there for. But you can’t talk about it for five… You can talk about it for a certain period of time and you know what you’re getting. But that’s a talent. That’s a talent where you can do that.”

“Most people I’d send in, number one, they wouldn’t be accepted. Number two, if they were, were, the meeting would last five minutes,” Trump added. “And that’s what happens with Steve. Everybody loves him. They love him on this side. They love him on the other side. And he really is, he’s a great negotiator because he’s a great guy.”

The media isn’t convinced, however.

“Trump bets Personal Diplomacy Will Break the Ukraine War Logjam,” ventured Vera Bergengruen and Annie Linskey for the Wall Street Journal on October 17, 2025. “The strategy isn’t without risks, with some critics worried a coming summit gives Russia more time to prosecute the war.”

“Trump’s decision to organize another high-profile summit with Putin isn’t without risk,” they surmised. “Trump’s previous meeting with the Russian leader ended without concrete success and was widely seen as a win for Moscow. Trump has so far been reluctant to ratchet up pressure on Putin, and the president’s critics worry that another summit allows Russia to buy more time to execute its war plans.”

The “coming summit” doesn’t “give” Russia more time to prosecute anything, however.

Vladimir Putin has already had all the time he wanted or needed to fulfill his ambitions for Ukraine.

Trump is also likely banking on a great deal more than “Personal Diplomacy” (whatever that is).

(Contributing writer, Brooke Bell)