Diplomatic winds are shifting across Eastern Europe, and the world is watching as U.S. President Donald Trump’s administration forges ahead with a flurry of new moves on Belarus and Ukraine. In the span of just a few weeks, the U.S. has overseen prisoner releases in Belarus, partially lifted sanctions on its national airline, and opened the door to supplying Ukraine with long-range missiles. But with every step, questions swirl: Is this a genuine humanitarian breakthrough, a calculated geopolitical gamble, or a diplomatic stalemate in the making?
It all began in earnest on September 11, 2025, when Trump’s envoy, John Coale, landed in Minsk. According to The Kyiv Independent, Coale’s visit secured the release of 52 prisoners from Belarusian jails and prompted the U.S. to ease sanctions on Belavia, Belarus’s state airline. More releases are reportedly in the pipeline, raising hopes for hundreds of families. For Belarusian strongman Alexander Lukashenko, the payoff is clear: a slow but steady thaw in relations with the West and the loosening of economic strangleholds that have long isolated his regime.
But what’s in it for Washington? The answer, it seems, is as much about symbolism as substance. The U.S. began exploring backchannels with Minsk over a year ago, when Joe Biden was still in the Oval Office. But negotiations picked up speed after Trump’s return in January 2025, with the White House eyeing Lukashenko as a potential intermediary in future peace talks with Russia’s Vladimir Putin. According to journalist Simon Shuster, this year of secret diplomacy paved the way for the much-hyped but ultimately fruitless Alaska summit in August. Yet, the process also drew Trump’s personal attention to the plight of Belarus’s more than 1,100 political prisoners—a cause he’s referenced multiple times on his Truth Social platform and in White House briefings.
“Trump’s administration somehow managed to sell it to him as a potential humanitarian victory. (…) Trump wants to have a traditional victory as a great leader who freed more than 1,000 hostages,” explained Artsiom Shraibman, a nonresident scholar at the Carnegie Russia Eurasia Center, in comments to The Kyiv Independent. Shraibman described Washington’s approach as “highly personalistic and fragile,” hinging on Trump’s own interest and appetite for a legacy-defining win.
The recent prisoner releases, which included opposition activist Siarhei Tsikhanouski and U.S. citizens, were initially met with little more than social media applause and diplomatic visits. But the latest batch of 52 freed detainees finally triggered a concrete concession: the partial lifting of U.S. sanctions on Belavia. The move, however, comes with strings attached. While restrictions were removed from eight planes, the Boeing 737-8EV reserved for Lukashenko himself remains blacklisted. And flights to Russia, Cuba, Iran, North Korea, and Russian-occupied regions of Ukraine are still off-limits. The U.S. Bureau of Industry and Security will now review Belavia’s aircraft parts requests individually, ensuring nothing is diverted to Russia or other “unsupported” destinations.
“President Trump feels that if you can have a relationship with people with whom you wouldn’t have had in the past, but try to build it up, then maybe we wouldn’t have as many wars on the table,” John Coale told DWS News, framing the prisoner releases as a step toward “normalizing relations.”
But humanitarian gestures aren’t the only motive in play. Regional security looms large, especially as the U.S. seeks to carve out a voice in the Russian political system. Dr. Ryhor Astapenia, director of the Belarus Initiative at Chatham House, told The Kyiv Independent that “the Trump administration would like to have a voice within the Russian political system (and at this point, they likely view Lukashenko as a certain representative of it) to talk more about de-escalation.” He added, “The rhetoric about the need for peace and negotiations used by Trump and Lukashenko is quite similar.”
Astapenia also noted that, given Belarus’s deepening dependence on Russia, the U.S. may be trying to buy time. “Looking at the increased Belarusian dependence on Russia over the past five years, (Trump’s administration) has likely come to the sad conclusion that Belarus might cease to exist in another 5-10 years under this regime. Stretching this process out for another 20 seems a better prospect.”
Lukashenko, for his part, is eager to capitalize. He’s seeking not just restored diplomatic ties but also the lifting of U.S. sanctions on Belarusian banks and the country’s lucrative potash fertilizer sector. He’s played this game before: in 2015, he freed political prisoners to curry favor with the West and hosted peace talks over the war in Ukraine. Dzianis Kuchynski, a diplomatic advisor to opposition leader Sviatlana Tsikhanouskaya, told The Kyiv Independent that a repeat scenario would suit Lukashenko just fine. But, he warned, “Lukashenko is even more dependent on Putin. Without him, Lukashenko would last about as long as a scuba diver without an oxygen tank. He might swim for a little while, but he would not reach the surface.”
Negotiations, according to Kuchynski, are unfolding on two tracks: humanitarian (focused on freeing detainees) and political (aimed at halting repression and moving toward democratization and, eventually, free elections). Yet, the road ahead is littered with obstacles. Trump’s highly personalized engagement could fade, Russia-Ukraine talks might stall, and European sanctions remain firmly in place. Lithuania and Poland, both of which have suffered from Belarus’s actions and Russia’s aggression, are holding the line on sanctions. “We don’t see that the European Union has any appetite right now to change its policy towards Lukashenko, lift some sanctions from him, or do some legitimization reset with him,” Kuchynski said.
Still, Shraibman sees potential value in the process. The last thaw in 2015 gave Belarusian civil society breathing room, which ultimately led to the 2020 mass protests. “But honestly, this is still hardly a reason not to try to save people’s lives in this process. And perhaps that is valuable in itself.”
Meanwhile, U.S. policy on Ukraine is evolving rapidly. General Keith Kellogg, the U.S. Special Representative for Ukraine, revealed on Fox News that President Trump authorized long-range strikes by Ukraine against Russia, though the Pentagon sometimes withheld permission for operational reasons. Vice President J.D. Vance confirmed that the U.S. is weighing the supply of Tomahawk missiles to Kyiv, but the final call rests with Trump. Ukrainian President Volodymyr Zelensky pressed for these missiles during a meeting at the United Nations General Assembly, and Foreign Minister Andriy Sibiga confirmed that discussions with Trump included lifting the taboo on such weapon transfers.
“As of today, Trump’s position is balanced and supports Ukraine,” Zelensky said at the Warsaw Security Forum, as reported by UNN. “Our goal is to maintain the new U.S. attitude towards the war so that it corresponds to the European one.” He also made it clear that “Russia will not establish Ukraine’s borders, which are defined by the Constitution,” and expressed openness to diplomatic negotiations.
Vance, in a Fox News interview, acknowledged frustration in the White House over Russia’s refusal to engage in peace talks. “They’ve refused to sit down with any trilateral meetings where the president or some other member of the administration could sit down with the Russians and the Ukrainians.” Trump, for his part, took to Truth Social to declare, “Ukraine, with the support of the European Union, is in a position to fight and win all of Ukraine back in its original form.”
As the U.S. continues to send Patriot air defenses and HIMARS rocket systems to Ukraine, the stakes couldn’t be higher. Analysts agree that the deployment of long-range missiles and other advanced systems must be weighed carefully, with diplomacy and civilian safety at the forefront. The world may not know yet whether Trump’s Belarus and Ukraine gambits will yield lasting peace or simply rearrange old fault lines. But for now, the region is holding its breath—and hoping for more than just a fleeting thaw.
