Special envoys Steve Witkoff and Jared Kushner are set to travel to Moscow for a meeting with Russian President Vladimir Putin before continuing on to Kyiv, where they will hold talks with Ukrainian President Volodymyr Zelensky. The trip, expected to take place September 5-6, would mark the envoys' first visit to the Ukrainian capital since President Donald Trump returned to office, and comes two days after a Russian jet-powered drone struck the headquarters of Ukraine's Security Service in central Kyiv.
According to a Russian outlet report cited by the Denver Gazette, Kushner and Witkoff will arrive in Moscow and then Kyiv on September 5-6. Trump confirmed the pair will meet Putin at the Kremlin before traveling on to Ukraine, saying he sent the two envoys to determine whether an agreement could be reached. The president has said the broader conflict is being impeded by personal hostility between Putin and Zelensky. Neither Kushner nor Witkoff had visited Kyiv since Russia's full-scale invasion began in February 2022, despite multiple trips to Moscow, according to DW News — a gap that had generated frustration among Ukrainian officials who repeatedly urged the envoys to conduct on-the-ground talks. The last time the two men visited Moscow to meet with Putin and other officials was in January.
Kyiv Struck Two Days Before the Envoys' Planned Arrival
The timing is stark. A Russian jet-powered drone struck the central headquarters of Ukraine's Security Service, or SBU, in Kyiv on Friday, September 4, directly targeting the office of acting SBU chief Oleksandr Poklad and injuring at least seven people, per the Financial Times. The strike hit a high-security government facility located near the UNESCO-protected St. Sophia Cathedral, underscoring the dangerous security environment in the capital just as the American delegation prepares to arrive.
In response, Zelensky announced Thursday that Ukraine has pledged to refrain from conducting aerial strikes against Russian targets during the envoys' visit to guarantee their safety, while calling on Moscow to observe a reciprocal pause, according to The Kyiv Independent. Sources within the Armed Forces of Ukraine told the outlet that front-line military units have been issued orders to halt fighting from midnight Saturday through September 8, spanning the envoys' diplomatic travel. Officials had not formally confirmed a bilateral ceasefire as of Thursday.
A Deal That May Require Putin to Bend
Jan Techau, a senior fellow at the Center for European Policy Analysis, said the envoys are seeking a deal that could make Putin more flexible on Ukraine and initiate negotiations, though he cautioned that Putin has not changed his position on the war and that previous visits have produced little outcome in the Ukraine context. Techau said he is not optimistic that Kushner and Witkoff will achieve their objectives in Moscow, noting that Putin has demands requiring Ukraine to concede before negotiations even begin — terms Ukraine considers unacceptable. Still, Techau said the envoys could carry an acceptable Russian negotiating position back to Kyiv if talks at the Kremlin go well.
The diplomatic push follows intense behind-the-scenes maneuvering by CIA Director John Ratcliffe, who met his Russian counterpart in Moscow less than two weeks before Thursday — a trip Trump has called a semi-routine meeting. During that covert visit on August 25, Ratcliffe proposed a trilateral peace summit between Trump, Putin, and Zelensky, according to Axios. As Hoodline reported in an earlier dispatch on the Moscow trip, U.S. and Russian officials had initially denied reports of Ratcliffe's visit. Ratcliffe met directly with FSB Director Alexander Bortnikov and SVR Foreign Intelligence Chief Sergey Naryshkin, spending roughly eight hours on the ground, though Kremlin spokesperson Dmitry Peskov confirmed he did not meet personally with Putin, per CBS News.
Mixed Signals on What Ratcliffe Actually Discussed
The purpose and substance of Ratcliffe's Moscow meetings remain largely unknown. Reports have suggested variously that Ratcliffe cautioned Russia against aiding Iran's government, that he visited Moscow to press for peace with Ukraine, and that he warned Russia against a hypothetical invasion of the Baltic states. During the same meeting, Ratcliffe formally requested that Russian intelligence agencies refrain from providing Middle East military intelligence to Iran that could be used against U.S. forces, according to reporting reviewed by NBC News.
Despite the intelligence outreach, Russian forces intensified missile and jet-drone attacks against Ukrainian energy, water, and civilian infrastructure in the days that followed, according to The Washington Post, with Russian military leadership reportedly believing Ukrainian air defenses were nearing exhaustion. Ukrainian air defenses have faced severe vulnerability in late August and early September due to a critical shortage of U.S.-made Patriot interceptor missiles, even as they try to counter jet-powered Russian drones traveling at speeds up to 250 mph, according to The Guardian, which noted Russia has launched nightly barrages of up to 800 drones. According to Congress.gov, the proposed Supporting Ukraine Act of 2025 included emergency appropriations for Defense Department assistance to Ukraine, including air defense, for the fiscal year ending September 30, 2025.
Manpower Strain Shapes Moscow's Calculus
Behind Russia's continued bombardment lies a steep human cost. Intelligence estimates in late August indicated Russia had sustained approximately 1.4 million total military casualties since February 2022, leading Kremlin planners to prepare for a potential mobilization of 600,000 additional troops, according to CBC News, without establishing a trend in volunteer recruitment inside Russia. That strain forms part of the backdrop as Witkoff and Kushner prepare for a Kremlin sit-down that could shape whether Moscow shows any new flexibility toward Kyiv — a question Techau says remains very much unresolved even as the envoys make their long-awaited trip.
