San Francisco Frontiers - Steve Witkoff, neophyte diplomat turned Trump's global fixer

Much like President Donald Trump -- for years his friend and golfing partner -- Witkoff came to the world stage without traditional experience. Instead, he relies on what the two men believe is a successful instinct in human relations and deal-making.

For Trump, the 68-year-old Witkoff brings the quality the president most cherishes: personal loyalty. But Witkoff has drawn wide criticism from those who believe he is out of his depth and has shown too much deference to Russian President Vladimir Putin, whom he met in Moscow on Tuesday.

"I liked him. I thought he was straight up with me," Witkoff said in March after meeting Putin, who has ruthlessly targeted 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," Witkoff said.

More recently, Bloomberg News reported a telephone conversation in which Witkoff offered advice to one of Putin's advisors on the best way to present to Trump a plan to end the Ukraine war.

According to the transcript, Witkoff said during the call that he believes Russia -- which started the war in Ukraine by launching a full-scale invasion in February 2022 -- "has always wanted a peace deal" and that he has "the deepest respect for President Putin."

Witkoff flew to Moscow with Trump's son-in-law, Jared Kushner, after meeting Ukrainian negotiators in Florida.

An initial version of the plan would ask Ukraine to cede territory that Russia has not won on the battlefield in return for security promises to Ukraine that fall well short of Kyiv's hopes to join NATO.

Trump has fumed about billions of dollars in US assistance to Ukraine and mused in the past that time was on Russia's side.

- Unorthodox approach -

It was the latest trip this year to Russia by Witkoff, who was tapped after Trump's election victory last year as his special envoy on the Middle East and quickly expanded his remit beyond negotiating two ceasefires in Gaza.

Witkoff quickly showed he was willing to break traditions to get deals. He worked alongside the outgoing administration of Joe Biden for the first of the ceasefires.

At one point, Witkoff flew from the discussions in Qatar to Israel to personally press Israeli Prime Minister Benjamin Netanyahu to accept. It was an unusual meeting held on Saturday, when official Israel is closed due to the Jewish Sabbath -- Witkoff is also Jewish.

In another break with protocol, Witkoff has met directly with representatives of Hamas, which the United States bans as a terrorist group, to push them on a deal.

After Israel targeted Hamas leaders meeting in September in Qatar, a close US partner, Witkoff personally offered condolences in Cairo to the top Hamas negotiator, Khalil al-Haya, whose son was killed in the Israeli strike.

"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 program "60 Minutes."

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

Witkoff was born in the Bronx and made his fortune in real estate, first as a lawyer and later as head of a property group. Forbes estimates his wealth at $2 billion.

R.Baker--SFF