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Questionable Trump insider’s rise began with a 3 a.m. ham-and-swiss sandwich: report

July 22, 2026
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Questionable Trump insider’s rise began with a 3 a.m. ham-and-swiss sandwich: report

President Donald Trump‘s relationship with peace envoy Steve Witkoff started in an unusual way — over a deli sandwich, according to a Slate report on Wednesday.

Journalist and author Andrea Bernstein described her encounter with Witkoff, the Trump insider, whose financial ties have come under scrutiny as he works as “Special Envoy for Peace Missions.”

“He looks like a grandpa, and sounds a little like a Jewish sidekick in a Pixar movie,” Bernstein wrote. “I’d known of him as a New York real estate mogul from covering Trump’s first presidency, and New York politics and real estate before that, but only vaguely. One day, I leaned forward to ask Witkoff what brought him to the courtroom that day. He told me he’d come for his friend. That word stuck with me: friend.”

That friendship started in the 1980s, around 3 a.m. in New York City, Witkoff has said.

“And he was—I knew who he was. He didn’t know who I was. And he didn’t have any money with him, and I was ordering from a local delicatessen for the people who were on my team. And he asked me if I would order him a ham-and-Swiss sandwich,” according to the report. “Witkoff did. Years later, when the two ran into each other again, Witkoff said, ‘he actually remembered who I was, and remembered the sandwich incident. And we just, you know, had just developed a, you know, a friendship as a result of it.’”

That relationship eventually led him into Trump’s administration. Since then, a number of questions have surfaced over Witkoff’s business dealings amid his negotiating role representing the Trump administration with Ukraine and Russia, and in the Middle East.

“The Iranians see Witkoff’s business ties to the UAE, and Jared Kushner’s ties to the Saudis, not to mention Israel, as cause for deep suspicion as well, people familiar with Iranian negotiators told me,” Bernstein wrote. “Saying that Kushner ‘is a volunteer’ with a ‘record of success in helping the President,’ Kelly maintained that ‘his private business activities have nothing to do with the President or the administration.’”

“Even in Witkoff’s earliest encounters, ‘there were concerns about Witkoff business ties,’ including his earlier dealings with Qatar and the UAE, said Seyed Hossein Mousavian, a former Iranian diplomat who moved to the U.S. and became a scholar at Princeton University,” Bernstein wrote. “‘They knew he had close ties to Netanyahu.’ The Iranians believed that ‘Witkoff had meetings with high-level Israelis before and immediately after’ he met with them, Mousavian said.”

The White House has denied any conflicts of interest.

“Mr. Witkoff, like all Administration officials, takes seriously his compliance with the government ethics rules,” the White House counsel, David Warrington, told Slate. “As Special Envoy for Peace Missions, he has not and does not participate in any official matters that could impact his financial interests. He has also divested from World Liberty Financial, notwithstanding his ability and willingness to recuse.”

The post Questionable Trump insider’s rise began with a 3 a.m. ham-and-swiss sandwich: report appeared first on Raw Story.

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