Witkoff’s arrival in Moscow comes as Trump hardens his rhetoric toward the Kremlin. Initially critical of Ukrainian President Volodymyr Zelenskiy, Trump has grown increasingly frustrated with Putin, citing recent drone attacks on Ukrainian cities as a turning point. In a CNBC interview, Trump suggested Russia’s economy is weakening and argued that further drops in global energy prices could force Putin to retreat. “If energy goes down another $10 a barrel, he’s going to have no choice,” Trump said, adding, “his economy stinks.”

To accelerate pressure, Trump has threatened secondary sanctions on countries buying Russian oil—a tactic fraught with geopolitical risk. While designed to curb Moscow’s war chest, such measures could also strain relations with India and China, major buyers of Russian energy. Trump has already clashed with New Delhi, threatening to raise tariffs, and warned that penalizing Beijing could derail an emerging trade truce.

Concerns Grow Over Envoy's Approach

European officials have privately expressed unease that Witkoff might be overly accommodating to Russian demands. A European diplomat noted that Witkoff is perceived as the Trump administration’s most sympathetic ear to Moscow, raising doubts about whether the envoy can extract meaningful commitments from Putin. The same diplomat warned that Russia may simply seek to prolong the war while avoiding punishment.

Zelenskiy, who spoke with Trump by phone on Tuesday, described the conversation as “productive.” Reports also indicate that U.S. special envoy Keith Kellogg is expected in Kyiv by week’s end. The diplomatic push follows months of appeals by European leaders urging Trump to re-engage after earlier threats to disengage from peace efforts.

The political stakes are high for Trump, who has repeatedly delayed sanctions to keep negotiations open. A failure to follow through this time could feed criticism that the president backs down under pressure—a narrative already dubbed “Trump Always Chickens Out” by some investors. Meanwhile, U.S. domestic concerns, including high gas prices and energy supply issues, add further urgency to the administration’s balancing act.