Starting out as a billionaire, investor and real estate developer, Mr. Steven Witkoff (67 years old) is gradually asserting his position in the diplomatic arena. He has continuously appeared at the ceasefire negotiation tables in the Middle East before and now Russia - Ukraine.

From Gaza to Ukraine

According to CNN, during Mr. Trump's 2024 US presidential campaign, Mr. Witkoff acted as a personal diplomat for the billionaire, facilitating negotiations with some of his top Republican rivals.

During the first month of Mr. Trump’s presidency, Mr. Witkoff traveled the world on behalf of the White House boss, meeting with leaders including Russian President Vladimir Putin.

Mr. Witkoff's first "achievement" during President Trump's early term was to promote ceasefire negotiations in the Gaza Strip.

On January 15, Israel and the Palestinian Islamist group Hamas officially reached a ceasefire agreement after 15 months of conflict. By the end of January, US special envoy for the Middle East Witkoff became the first US government official to visit the Gaza Strip in many years.

Then, in early February, billionaire Witkoff unexpectedly met Russian President Putin in a private meeting. Speaking at an investment conference in Miami (Florida, USA) in February 2025, Mr. Witkoff revealed that he spent the entire meeting developing a friendship and relationship with President Putin.

According to the New York Times , Mr. Witkoff appeared to have felt comfortable with the Russian leader, even though the two had just met for the first time.

This newspaper commented that approaching Russian President Putin is not an easy task, making even a veteran diplomat "suffocate". Because before becoming the leader of Russia, Mr. Putin was an intelligence agent.

The meeting helped Washington successfully exchange a number of prisoners with Moscow, including Marc Fogel, an American citizen serving a prison sentence in Russia for marijuana smuggling.

Become the 'king of negotiation'

Speaking to NBC News after the talks in Gaza, a Middle Eastern diplomat described Mr. Witkoff as a tough negotiator, but still showing soft spots.

The US media also called Mr. Witkoff a special envoy specializing in diplomatic negotiations with the style of a "real estate tycoon" going to make deals.

At the time, Mr. Witkoff expressed his sympathy for parents who had lost children in the conflict, whether Israeli or Palestinian, through his own story of losing a child. Mr. Witkoff did not hesitate to share the story of his son Andrew, who died at the age of 22 in 2011 from an overdose of the painkiller OxyContin.

In the Russia-Ukraine story, Mr. Witkoff once expressed a different perspective when he refuted the idea that Russia is a “dangerous invader”. Responding to CNN in February 2025, Mr. Witkoff said that Moscow’s military campaign in Ukraine was “provoked”.

Some have argued that Mr Witkoff's unusual remarks show flexibility and a more "open-minded", easy-going, and gentler perspective.

At the meeting on March 11, Mr. Witkoff, along with US Secretary of State Marco Rubio, attended the ceasefire negotiations between Russia and Ukraine in Jeddah, Saudi Arabia. However, the US media could not help but wonder about the absence of President Trump's special envoy for Russia and Ukraine, Keith Kellogg, at the negotiations in Saudi Arabia.

Observers say that special envoy Kellogg seems to have been “sidelined” because of his somewhat “hawkish” and rigid views on Russia. Previously, Mr. Kellogg was the one who continuously urged Washington to pump more military aid into Ukraine as well as always tried to ensure security to help Kiev sit at the negotiating table with Moscow in a “superior” position.

Two sources familiar with the matter told CNN that Moscow had indicated that it would rather negotiate with Witkoff than Kellogg. The White House, however, has denied the reports.

Responding to CNN, some people who attended joint meetings with Mr. Witkoff described the Jewish-American billionaire as a kind but straightforward person, a “more polite version” of President Trump, a sociable person who knew how to use “communication levers” at the right time to help ease some tense negotiations.

Sources close to President Trump also said Mr. Trump soon believed that Mr. Witkoff had honed his negotiating skills through his real estate career.

Experts also said that Mr. Witkoff has an advantage over other senior officials of President Trump in that Mr. Witkoff has known Mr. Trump for a long time and knows his "ways and moves".