President Donald Trump seemingly remains unperturbed that one of his envoys reportedly provided counsel to the opposing party in ongoing foreign-policy discussions.

This development follows a report published by Bloomberg on Tuesday, which unveiled a purported transcript. The transcript allegedly captures U.S. Special Envoy for Peace Missions Steve Witkoff, known for his role in mediating the ceasefire between Israel and Hamas in Gaza and currently engaged in U.S. efforts to broker peace between Russia and Ukraine, advising Vladimir Putin’s senior foreign policy adviser Yuri Ushakov on how the Kremlin could most effectively communicate with Trump.

According to the transcript, which TIME has not been able to independently corroborate, Witkoff suggested during an October 14 conversation with Ushakov that Putin should engage in a phone call with Trump before the U.S. President was scheduled to hold a meeting. Witkoff also recommended that Putin “congratulate” Trump and commend him as a “man of peace.”

Witkoff proposed that instead of Putin delving into the intricate details of potential sacrifices a deal might require, they should “discuss things more optimistically… And I believe, Yuri, the president will grant me significant latitude and discretion to finalize the agreement.”

Putin reportedly acted on this advice. A Kremlin statement indicated that Putin “commenced by commending Donald Trump on his successful initiatives to normalize the situation in the Gaza Strip.” Weeks later, the Trump Administration revealed a peace proposal for Ukraine that was reportedly rejected by Kyiv. Observers noted that it appeared to heavily favor Russia’s interests, and TIME has previously reported that it drew extensively from a document outlining Russia’s prerequisites for ending the conflict.

The Bloomberg report detailing Witkoff’s conversation—coupled with the subsequent peace proposal seen as favorable to Russia—has prompted skepticism from certain critics regarding Witkoff’s loyalties.

“An actual traitor,” stated Democratic Rep. Ted Lieu of California.

“It is evident that Witkoff entirely favors the Russians. He cannot be trusted to lead these negotiations,” asserted Republican Sen. Ben Sasse of Nebraska. “Would a paid Russian agent accomplish less than he? He should be dismissed.”

However, just as Witkoff had foretold in his discussion with Ushakov, Trump reaffirmed his confidence in Witkoff to iron out the necessary details for achieving the agreement.

White House communications director Steven Cheung, in a written statement, described Witkoff as a “successful negotiator” and stated that “there is nothing improper about what was said” during the call.

“That is a standard practice,” Trump remarked on Tuesday when questioned about Witkoff’s reported private discussion with the Russian official. “That’s what a dealmaker does.”

On Truth Social, Trump announced that Witkoff would travel to Moscow to meet with Putin to finalize the peace plan.

Who is Steve Witkoff?

Witkoff has become recognized as one of Washington’s foremost diplomats and negotiators, with the Atlantic even labeling him Trump’s “shadow Secretary of State.”

The special envoy spearheaded discussions with Russia at the outset of Trump’s second term to secure the release of American prisoner Marc Fogel, was central to negotiations for a ceasefire between Israel and Hamas, and has become the primary contact for talks with Russia concerning the cessation of the war in Ukraine.

Yet, prior to these roles, he had been a friend and associate of Trump’s for many decades.

When he testified during Trump’s fraud trial in 2023, Witkoff recounted that his friendship with Trump began at a New York deli in 1986. Witkoff, then a young lawyer, had previously worked for the firm Dreyer & Traub, where Trump was a client, and the two had collaborated on a transaction. “I ordered him a ham and swiss,” Witkoff stated, according to the New York Times, which also reported Witkoff’s recollection that Trump had no cash. Trump would remember that interaction several years later, Witkoff noted, sparking a friendship so profound that Witkoff served as his best man. During the Republican National Convention last year, Witkoff delivered a eulogy for Trump when he lost his son Andrew to an opioid overdose in 2011.

Over the years, Witkoff contributed millions to Trump’s political campaigns, and during Trump’s first term, he informally advised the administration. When Trump emerged victorious in the 2024 elections, Witkoff was appointed as a senior advisor. Days later, Trump declared that Witkoff would serve as his special envoy to the Middle East, despite his limited prior diplomatic experience.

Foreign ties under scrutiny

Earlier this year, the New York Times reported that Witkoff’s diplomatic activities, particularly in the Middle East, occasionally appeared to intertwine with his business interests—a parallel drawn to former Secretary of State Mike Pompeo. More recently, critics have raised additional concerns about his connections abroad.

Witkoff’s responsibilities expanded beyond the Middle East in March, when Trump altered the mandate of his previously appointed envoy for the Russia-Ukraine conflict, Keith Kellogg, to focus solely on Ukraine, thereby entrusting Witkoff with negotiations concerning Russia.

Witkoff faced early criticism from Zelensky and others for appearing to favor Moscow and even reportedly using outdated maps during diplomatic discussions.

Several journalists and social media users have since brought up Witkoff’s past associations with Russian figures in the wake of Bloomberg’s report.

Ine Iversen, an independent reporter covering Ukraine, posted on X a claim that Witkoff “has spent three decades immersed in Russian money, Russian mob circles, and the Russian real-estate pipeline.” Others have referenced American journalist Craig Unger, who recently wrote about what he described as Witkoff’s ties to the “Russian Mafia.”

Iversen and Unger highlighted how real estate magazine The Real Deal reported in 2013 that Witkoff provided a recommendation for indicted Russian mobster Anatoly Golubchik when Golubchik sought residency in a New York condominium building.

On X, some users have made connections to Len Blavatnik, a Ukraine-born businessman who partnered with Russian billionaire Viktor Vekselberg. Vekselberg was sanctioned by the U.S. for his links to Putin, while Blavatnik, despite divesting from Russian assets following Russia’s 2022 invasion of Ukraine, faced scrutiny in 2023 due to national security concerns.