Former President Donald Trump is advancing efforts to engage directly with Russian President Vladimir Putin amid ongoing tensions over the war in Ukraine, including discussions of a potential hostage release and broader diplomatic negotiations aimed at reshaping U.S.-Russia relations.

Reports indicate that Jared Kushner, a senior adviser to Mr. Trump, is expected to travel to St. Petersburg, Russia, to meet with Mr. Putin. The anticipated trip aligns with attempts to secure the release of an American detained in Russia. The only individual classified by the U.S. State Department as “wrongfully detained” there is Stephen Hubbard, an elderly American who was captured in 2022 and subsequently sentenced to more than six years in a penal colony on charges of mercenary activity linked to Ukraine.

The timing of any release appears strategic, amid the U.S. midterm election cycle, potentially allowing Mr. Trump to portray himself as prioritizing an “America First” foreign policy by facilitating the return of an American prisoner. However, the broader objective for both Mr. Trump and Mr. Putin seems focused on normalizing relations after years of strain following Russia’s 2014 annexation of Crimea and military actions in eastern Ukraine, which had prompted sanctions from the United States and Europe.

Historical attempts at rapprochement, such as the Nord Stream 2 pipeline agreement under former German Chancellor Angela Merkel, ultimately failed to prevent deeper conflict, culminating in Russia’s full-scale invasion of Ukraine in 2022. In this context, Mr. Trump appears to be pursuing a more expansive diplomatic strategy, with plans reportedly being discussed for a three-way meeting involving Mr. Putin and Chinese President Xi Jinping at a Pacific Rim summit. The purported agenda includes discussions on arms control and denuclearization, although none of the parties have indicated a willingness to eliminate their nuclear arsenals.

Such a summit, if it occurs, would mirror past historic conferences where global powers delineated spheres of influence, raising concerns about a potential reordering of international relations that sidelines Ukraine’s territorial sovereignty. Additionally, a forthcoming meeting at a G20 summit hosted by Mr. Trump’s Florida resort would mark a notable step in reintegrating Mr. Putin into global diplomatic forums.

Nevertheless, Mr. Trump’s approach has faced criticism for appearing to shift U.S. policy away from supporting Ukraine’s sovereignty and defense. Ukrainian officials express skepticism that the United States would uphold security guarantees or military aid under a Trump administration. Richard Haass, a veteran diplomat, characterized such a policy reversal as unprecedented, noting that the U.S. rarely “switches sides” in conflicts, particularly by penalizing the victim of an invasion and rewarding the aggressor.

Comparisons to other historical shifts in U.S. foreign policy, such as President Richard Nixon’s opening to China or the withdrawal from Vietnam and Afghanistan, underscore the singular nature of the current situation, given the active war and the introduction of potential economic agreements with Russia’s leadership.

Mr. Trump’s advisors emphasize that the conflict between Russia and Ukraine is at a critical juncture, asserting that the next move must come from Ukrainian President Volodymyr Zelensky. They urge Mr. Zelensky to demonstrate a willingness to negotiate with Russia, possibly conceding territorial claims. This stance contrasts with Mr. Zelensky’s previous commitments to uphold Ukraine’s sovereignty, declarations that previously garnered strong bipartisan support from the U.S. Congress and assurances of continued American assistance.

In recent remarks, Mr. Zelensky acknowledged the changed diplomatic environment, warning that if the United States were to side with Russia, Ukraine would struggle to maintain its position in the conflict. As discussions continue, the future shape of U.S. involvement and the prospects for peace in the region remain uncertain.