Following a significant diplomatic victory in the Middle East, President Donald Trump appears to be enjoying a wave of support, even from some of his skeptics. However, White House aides remain cautious, aware of the president’s history with a formidable rival.

According to a White House insider familiar with discussions about President Trump’s recent engagement with Ukrainian President Volodymyr Zelenskyy, the president is feeling ambitious yet remains clear-eyed about the tactics of Russian President Vladimir Putin.

“Trump believes he has momentum to address this issue, but he’s deeply frustrated with Putin, feeling that Putin is undermining his image on the global stage,” the source explained.

The aide highlighted that Trump is approaching Putin with increased skepticism, prepared to adopt more assertive strategies if necessary.

In a “productive” phone conversation with Putin on Thursday, the two leaders agreed to initiate new peace negotiations in Hungary in the coming weeks, though no specific date has been set.

Analysts caution that while the recent ceasefire between Israel and Gaza, along with the exchange of hostages and prisoners, was a complex achievement, navigating the unpredictability of Putin presents an even greater challenge.

Putin commands a nuclear arsenal, controls Europe’s energy supply and has shown no signs of backing down after almost four years of grinding war in Ukraine.

‘Putin is a mob boss. Hamas are street thugs,’ said Len Khodorkovsky, a former deputy assistant secretary of state.

‘Putin is a master manipulator… former KGB,’ said a former senior defense official in the Biden administration. ‘He’s made it clear he wants to continue the war.’ 

A Ukrainian serviceman stands among the rubble in the courtyard of destroyed residential buildings in the frontline town of Kostyantynivka, Donetsk region, on Sunday

Ukrainian soldiers take part in trench training at a British base on Wednesday

Trump walks with Russian President Vladimir Putin as they arrives at Joint Base Elmendorf-Richardson on August 15 in Anchorage, Alaska

Since their frosty Oval Office clash in February, when Trump and Vice President JD Vance openly criticized Zelenskyy for what they called a ‘lack of gratitude,’ the dynamic between the American president and his Ukrainian counterpart has thawed.

Trump has moved from a hands–off approach with Putin to a tougher stance, even declaring that Ukraine could reclaim land taken by Russia. In a September Truth Social post, he labeled Russia a ‘paper tiger’ and, for the first time, called it the aggressor in the war.

President Trump is set to host Ukrainian President Volodymyr Zelenskyy at the White House on Friday, marking a clear shift toward strengthening US–Ukraine relations following months of pressure on Kyiv to make compromises in its conflict with Russia. 

A recent phone call between the two leaders reportedly included discussions about the potential transfer of long–range Tomahawk missiles to Kyiv, a topic expected to be revisited during their meeting.

According to the former senior Biden Defense Department official, Trump’s recent strong posture in Gaza means his high-pressure tactics are now taken very seriously.

‘Trump was able to strong–arm Netanyahu,’ the official said, pointing to his influence in the recent Gaza ceasefire negotiations.

Trump speaks to Israeli Prime Minister Benjamin Netanyahu at Ben Gurion International Airport before boarding his plane to Sharm El-Sheikh, on October 13 

In Tel Aviv, Israel on October 13, 2025, residents and families of hostages gathered at Hostage Square, awaiting the return of those held by Hamas as Israel and Hamas agreed on the first phase of a Gaza ceasefire deal 

Released Israeli hostage Avinatan Or greets well–wishers upon arriving at Beilinson Hospital in the Rabin Medical Centre in Petah Tikva in central Israel 

With Iran—the main funder of Hamas—’basically eliminated’ following the 12–day war, the official said, ‘that gave Trump the ability to go back to Netanyahu and basically say, enough is enough.’

The Senior Biden administration official warned that Ukraine presents a very different kind of challenge, even though Trump said this week it’s a war Putin should’ve won in a week. 

‘There’s no one capability that’s going to change the battlefield dynamics,’ the official said, noting that even advanced systems like Tomahawk missiles won’t present a silver bullet. ‘The way the war ends is at the negotiating table.’

Russia has an enormous army and vast battlefield resources. But its technology is generally thought to be far inferior to the western weapons that have flooded into Ukraine courtesy of the United States.  

John Sitilides, National Security Senior Fellow at the Foreign Policy Research Institute, observed that Russia is advancing its military campaign at a striking pace, in contrast to Hamas, whose military capabilities have dwindled—particularly as its primary backer, Iran, has been significantly weakened.

‘Russia continues to produce artillery shells and advanced drones at an astonishing rate, far surpassing the output of Ukraine or even NATO.’

Israeli soldiers salute as vehicles transporting the bodies of four hostages handed over following a ceasefire and prisoner exchange deal between Israel and Palestinian factions in Gaza, arrive to the National Center for Forensic Medicine in Tel Aviv on October 13

Trump greets Russia’s President Vladimir Putin, Friday, Aug. 15, 2025, at Joint Base Elmendorf-Richardson, Alaska 

Sitilides, a former State Department consultant, says Trump’s Middle East success has left Putin more isolated diplomatically. 

Putin relied on ties with now–weakened Iran and Syria and alienated Israel by aligning with pro–Palestinian forces. ‘Almost all of his Middle East partners are on the wrong side of the historic peace agreement,’ Sitilides said.

He cautioned that Putin is unlikely to engage in real peace talks unless major concessions are made, such as conceding Crimea, eastern Ukrainian territories, and Ukraine’s NATO exclusion. 

Meanwhile, a former Biden defense official noted the window for peace may be closing for both sides, as the Biden administration had prioritized maximizing Ukraine’s leverage before talks.

Still, the source argued the White House can take a key lesson from Trump’s recent Middle East breakthrough: ‘Friends and allies matter… When the whole region turns against you, that’s incredibly powerful,’ they said. ‘Standing shoulder to shoulder with more people is an incredible message to an aggressor.’