Political observers are starting to raise concerns about President-elect Donald Trump’s selection of Jewish real estate investor Steve Witkoff as his special envoy to the Middle East last week.

“Steve is a Highly Respected Leader in Business and Philanthropy, who has made every project and community he has been involved with stronger and more prosperous,” the announcement indicated. “Steve will be an unrelenting Voice for PEACE, and make us all proud.”

According to the Trump campaign, Witkoff, along with former Sen. Kelly Loeffler (R-GA), is also set to co-chair the 47th president’s inaugural committee.

In an interview with The Bulwark in May, Witkoff, founder of the Witkoff Group, which he started in 1977, explained that he secured “six-figure and seven-figure donations” for the Trump campaign from Jewish donors following Biden’s announcement he’d be pausing weapons shipments to Israel. (Related: War on Gaza: Trump’s cabinet is a recipe for all-out Middle East war.)

Critics noted that Witkoff has “no known experience with diplomacy or the Middle East.” Apart from openly expressing his pro-Israel stance, he even lauded the Israeli Prime Minister’s speech when he spoke at the U.S. Congress earlier this year.

He told Fox News that Netanyahu’s message was “strong and it was epic to be in that room.”

“It felt spiritual,” he added.

The Wall Street Journal published an article, highlighting Trump’s and Witkoff’s friendship going way back.

“Elon Musk may be Trump’s most visible new ‘bestie’ since throwing his weight and money behind the president-elect’s campaign, but Witkoff has been one of Trump’s closest and most constant friends on his climb back to power,” WSJ wrote.

It added that the New York investor traveled with Trump throughout his campaign and stayed with him at Mar-a-Lago in the week leading up to election day. He was even golfing with Trump on the day of an attempted assassination in September.

In April 2022, Witkoff’s son Zach and his wife Sophie Knight held their wedding reception at Trump’s Mar-a-Lago estate. Paying tribute that evening were Trump and his wife, who stayed late into the night to celebrate.

Also present at the event were Florida Gov. Ron DeSantis and a collection of real estate royalty, including Barry Sternlicht, and the baseball star Alex Rodriguez.

Why Trump chose a negotiator to be the Middle East envoy

As to why the president-elect chose another developer, as opposed to a diplomat, is perceived that Trump views the current Middle East crisis as a complicated property negotiation.

Incidentally, a person familiar with Witkoff’s thinking said that he thinks that the conflict is “one giant real estate deal.”

Insiders also reasoned that choosing someone who Trump is confident to work with whom he trusts would be able to carry on Jared Kushner’s approach. Kushner is Trump’s former senior advisor and Ivanka Trump’s husband, the incoming POTUS’ daughter.

Witkoff was at a Trump campaign event at Madison Square Garden in New York last month.

“His negotiating style was one where it was never adversarial,” said Don Peebles, another well-known developer who attended the Mar-a-Lago wedding, recalling their first dealings years ago. Witkoff is “not the kind of negotiator that wants to see blood on the floor before getting the deal done.”

However, critics have pointed out that he was Jewish and has been a staunch supporter of Israel.

Also, another real-estate executive sounded skeptical about Witkoff’s credentials even while praising his savvy. Peacemaking in the Middle East isn’t Witkoff’s world, this person said.

Witkoff may also have to finesse relationships closer to home. Kushner has indicated that he expects to remain involved — even without an official role. “I’ll give them my advice, I’ll help them in any way they need,” he told WSJ in a recent interview.

According to the news outlet, Witkoff plans to “speak with, collaborate and download with” Kushner, whom he believes has an “exceptional grasp of the dynamics” of the region, said a personal familiar with this thinking.

Moreover, Witkoff has shown his loyalty to the president-elect.

In fact, he came to Trump’s aid during the Manhattan fraud trial. He was the first to testify in his friend’s defense. He did this at a time when many previous supporters and donors were moving away to avoid being linked to Trump.

One of Witkoff’s real estate partners reached out towards the end of the campaign, asking when he would see him again. Witkoff, according to this person, declared: “I will stay with the president for the duration.”

He was among the tight circle of family and friends called to the stage to celebrate on election night.

He was also one of Trump’s biggest fundraisers. He provided a connection to Jewish donors, including Miriam Adelson, a staunch supporter of Israel who ultimately contributed $100 million and a regular companion on the campaign trail.

After Trump insulted Georgia Gov. Brian Kemp at a rally, Witkoff flew to Atlanta to smooth things over. Days later, Kemp went on Fox News to pledge his allegiance to Trump.

And when DeSantis bowed out of the race, Witkoff brokered a détente between the protégé-turned-challenger and Trump.

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Sources for this article include:

InformationLiberation.com

WSJ.com