Real Estate Mogul with No Diplomatic Experience, Trump’s 40-Year Confidant... Was Putin Behind His Rise?

Witkoff Visits Russia Six Times, Has Yet to Visit Ukraine

Reports have emerged that Russian President Vladimir Putin’s meticulous calculations were behind the rise in influence of billionaire real estate developer Steve Witkoff, who became a special envoy for U.S. President Donald Trump. Witkoff has no prior diplomatic experience.

On December 19 (local time), Yonhap News Agency cited the Wall Street Journal (WSJ), reporting that shortly after Witkoff was appointed as special envoy to the Middle East in Trump’s second administration, he received a message from Crown Prince Mohammed bin Salman stating that President Putin wanted to meet him. The proposal indicated that Putin wished to meet personally and was even willing to consider releasing American prisoners held in Russia to facilitate the meeting.

Volodymyr Zelensky, President of Ukraine, and Steve Witkowski, U.S. Special Envoy (from left). Photo by Yonhap News Agency

The condition for the meeting was that Witkoff come alone-without a CIA handler, diplomat, or interpreter. Following this, Witkoff met privately with President Putin in Moscow and subsequently brought back American detainee Marc Fogel in February. This event significantly elevated Witkoff’s status. The WSJ reported that President Putin had analyzed the “psychological profiles” of those around Trump to carefully select his point of contact.

At the time, retired Lieutenant General Keith Kellogg, who had been nominated as special envoy to Ukraine, was classified as an “unfriendly” figure because his daughter ran a charity related to Ukraine. Based on this assessment, President Putin reportedly chose Witkoff-who lacked diplomatic experience but enjoyed President Trump’s complete trust-over Kellogg.

As a result, Kellogg lost his footing on Ukraine issues, while Witkoff emerged as a key figure discussing border matters and even the timing of lifting sanctions against Russia, alongside Trump’s son-in-law Jared Kushner. The deep involvement of businessmen, rather than career diplomats, in discussions related to ending the war is considered unprecedented.

Recently, during his sixth visit to Russia, Witkoff held talks with President Putin for over five hours until midnight, while he has yet to visit Ukraine even once.

The WSJ pointed out that it is unprecedented for businessmen, rather than professional diplomats, to be so deeply involved in such critical issues of war and peace.

Meanwhile, on December 19 (local time), President Putin of Russia stated that Ukraine is not yet ready to discuss territorial issues, placing all responsibility for the start and resolution of the conflict on Ukraine. However, he added that he is receiving specific signals indicating Ukraine is prepared to engage in dialogue.