Steve Witkoff: From Business Tycoon to Trump’s Global Troubleshooter

The leading figure in negotiations to halt the Ukraine war is not a seasoned diplomat or the United States secretary of state, but billionaire property developer Steve Witkoff.

Much like President Donald Trump – his long-time friend and golfing companion – Witkoff stepped onto the global stage without traditional diplomatic credentials. Instead, he relies on what the pair believe to be a keen instinct for human interaction and deal-making.

For Trump, the 68-year-old offers what he values most: unshakeable personal loyalty. Yet Witkoff has faced strong criticism from those who argue he is out of his depth and has shown excessive deference towards Russian President Vladimir Putin, whom he met in Moscow on Tuesday.

“I liked him. I thought he was straight up with me,” Witkoff remarked in March after meeting Putin, who has long targeted his political opponents at home and abroad.

“I don’t regard Putin as a bad guy. That is a complicated situation, that war, and all the ingredients that led up to it,” he said.

More recently, Bloomberg News published details of a telephone conversation in which Witkoff appeared to advise one of Putin’s aides on how best to present a peace plan to Trump.

According to the transcript, Witkoff suggested during the call that Russia – which launched a full-scale invasion of Ukraine in February 2022 – “has always wanted a peace deal” and added that he holds “the deepest respect for President Putin”.

Witkoff travelled to Moscow alongside Trump’s son-in-law, Jared Kushner, after meeting Ukrainian negotiators in Florida.

An initial version of the plan reportedly asked Ukraine to surrender territory that Russia has not captured militarily, in exchange for security guarantees that fall significantly short of Kyiv’s aspirations for NATO membership.

Trump has repeatedly expressed frustration over billions of dollars in United States aid to Ukraine and previously hinted that time was working in Russia’s favour.

Unorthodox approach

The visit marked Witkoff’s latest trip to Russia this year. After Trump’s election victory in the previous year, he was appointed special envoy for the Middle East, quickly broadening his role beyond negotiating two ceasefires in Gaza.

Witkoff soon demonstrated his readiness to break from conventional diplomatic practice. He cooperated with the outgoing Biden administration during negotiations on the first ceasefire.

At one stage, Witkoff flew from Qatar to Israel to personally urge Prime Minister Benjamin Netanyahu to accept a deal. The meeting took place on Saturday, when official government offices are closed for the Jewish Sabbath – Witkoff himself is Jewish.

In another unorthodox move, he held direct talks with representatives of Hamas, which the United States designates as a terrorist organisation, in an effort to push them towards an agreement.

Following an Israeli strike in September that targeted Hamas leaders meeting in Qatar, a close partner of the United States, Witkoff expressed condolences in Cairo to senior Hamas negotiator Khalil al-Haya, whose son had been killed.

“I told him that I had lost a son, and that we were both members of a really bad club, parents who have buried children,” Witkoff later told CBS News programme 60 Minutes.

Witkoff frequently speaks about his son, Andrew, who died of an opioid overdose at the age of 22 in 2011.

Born in the Bronx, Witkoff built his fortune in real estate, beginning his career as a lawyer before founding his own property group. Forbes estimates his wealth at $2 billion.

Khaborwala/SS