The Mysterious Fourth Man At The Trump-Ye Dinner Tells His Story

When former President Donald Trump held a now-infamous dinner last month with Ye, the antisemitic rapper formerly known as Kanye West, and a prominent white nationalist, an unnamed additional guest sat alongside the powerful men. 

NBC News reported only that the other person in Ye’s group was the parent of a student at Donda Academy, the rapper’s private school in California. But while speaking about the dinner this week, Ye briefly referred to a man named Jamar Montgomery during a livestream with far-right influencer Tim Pool. Ye identified him as a “Boeing engineer.”

HuffPost tracked Montgomery down and spoke with him Thursday night. He is indeed a Boeing employee, though he did not confirm any connection with Donda Academy. Montgomery told a wild tale about how an invitation from Ye, whom he says he barely knew, quickly led to a dinner with the former leader of the free world. Montgomery shared some details from the evening, including some insight into why a mysterious phone call suddenly darkened Trump’s mood, after which he began treating Ye with open hostility.

Just a few days after Montgomery met Ye, he said Ye invited him to come along on a visit to Trump’s Mar-a-Lago resort.

Montgomery didn’t second-guess the invitation.

“All I know is he asked me,” Montgomery recalled to HuffPost. “He obviously felt that either my presence or my input was going to be valuable, and wanted me there, that’s as far as I can surmise.”

“I wasn’t necessarily going to ask, ‘Why do you want me there?’ It’s like looking a gift horse in the mouth. You’re asking me to go meet the former president? Uh, yes,” he said. 

The meeting was another stop on Ye’s 2024 presidential run — which so far has included saying he’s going “Death Con 3 on Jewish People,” and, more recently, praising Adolf Hitler and faulting “the Jewish media” for pushing the narrative that the Nazis “never offered us anything of value.” For Trump, the dinner has become a liability given Ye’s recent public antisemitism, as well as the well-documented bigotry of his other companion that night, Nick Fuentes, a white nationalist livestreamer. 

Montgomery told HuffPost he didn’t know about Fuentes’ views until after the meeting, and that as a civil rights activist, “I fight against Nazism.” 

But last week, he accepted Ye’s invitation. 

And so Montgomery flew from California to Florida, where Karen Giorno, an adviser to Trump’s 2016 campaign, drove the crew to Trump’s resort and home. A campaign adviser for Ye’s 2024 presidential bid, far-right influencer Milo Yiannopoulos, organized the dinner but did not attend, Montgomery said.

“Next thing you know, we’re having dinner on the patio at Mar-a-Lago,” he said.

Next thing you know, we’re having dinner on the patio at Mar-a-Lago.Jamar Montgomery, dinner guest at Mar-a-Lago

Montgomery said Ye initially reached out to him about two weeks ago to talk about education, given Montgomery’s experience as an educator and tutor.

Montgomery confirmed he worked for Boeing, but said, “the work that’s most important to me is the work that I do for the people.” He cited his efforts to teach his community about financial literacy, cryptocurrency and political science. A Boeing spokesperson confirmed to HuffPost that someone of the same name works for the company. The spokesperson declined to describe Montgomery’s work, citing privacy reasons, and said “we did not have an employee there representing Boeing in any official capacity.”

Montgomery ran for U.S. Senate in Louisiana in 2020 as a no-party-affiliation candidate, ultimately earning 5,804 votes, and he currently goes by the moniker “The Crypto Politician.”

And as for the dinner? “I was there as a spectator. I was just along for the ride.”

HuffPost was unable to reach Ye, Fuentes or Yiannopoulos for comment. Neither Giorno nor representatives for Trump immediately responded to HuffPost’s requests for comment.

“I wasn’t necessarily going to ask, ‘Why do you want me there?’ It’s like looking a gift horse in the mouth. You’re asking me to go meet the former president? Uh, yes,” Jamar Montgomery said of being invited to Mar-a-Lago.
“I wasn’t necessarily going to ask, ‘Why do you want me there?’ It’s like looking a gift horse in the mouth. You’re asking me to go meet the former president? Uh, yes,” Jamar Montgomery said of being invited to Mar-a-Lago.

“I wasn’t necessarily going to ask, ‘Why do you want me there?’ It’s like looking a gift horse in the mouth. You’re asking me to go meet the former president? Uh, yes,” Jamar Montgomery said of being invited to Mar-a-Lago.

‘Do You Want Your Friends To Come With You?’ 

If Mar-a-Lago had some sort of security protocol tasked with vetting him as a visitor, “I wasn’t quite aware,” Montgomery recalled. He said he’d heard before the visit that the group’s names were being sent to Mar-a-Lago staff, but once at the property, someone checked Giorno’s credentials and “saw Ye, saw us and about a minute or two later, went ahead and let us in.” 

After a few minutes sitting in Mar-a-Lago’s foyer, “the next thing we know, we see the president coming out.” 

Trump “seemed very excited” to see Ye, Montgomery recalled, but did not seem to recognize anyone else in the party, even Giorno, who later told Trump she was his campaign’s Florida state director in 2016. Nonetheless, Trump asked, “Do you want your friends to come with you?” to which Ye replied, “If it’s OK with you.” Trump agreed, Montgomery said.

The president would later claim he “knew nothing about” Fuentes. Montgomery also said that after he mentioned his own 2020 U.S. Senate bid in Louisiana, Trump was “trying to figure out who the senator in that state was.” 

Mar-a-Lago was “top notch,” with friendly staff, Montgomery said — “you knew that you were around wealth.” The group sat at a table in the middle of the patio, and at first, things were jovial. Trump did most of the talking, and allowed Ye to choose some of his music to play — something off of his “808s and Heartbreak,” Montgomery said, though he couldn’t recall which song. (It’s not his favorite album.)

“He was very charming, and very personable,” Montgomery recalled of the former president. 

Fuentes was “fawning over Trump and some of his speeches,” though, as has been reported elsewhere, he critiqued Trump’s recent speech announcing his 2024 candidacy as not as invigorating to Trump’s base as his initial 2016 campaign rhetoric, Montgomery said. Trump “seemed interested and wanted to hear a little bit more,” though Montgomery didn’t recall other details, other than that Trump didn’t seem to recognize Fuentes.

Then, things changed.

“All of the sudden, he gets a phone call, and the whole mood switches,” Montgomery said.

All of the sudden, he gets a phone call, and the whole mood switches.Montgomery

‘Some Of His Black Constituents’

Trump’s change in demeanor followed a phone call, which Axios first reported

Montgomery speculated the call may have been related to a mistakenly sent text message. During the dinner, Ye attempted to send a message to Fuentes, only to accidentally send it to an attorney, Montgomery recalled. Trump received a call shortly thereafter. A spokesperson for the attorney in question, Nick Gravante, denied to Newsweek that Gravante made any call to Trump nor anyone in his orbit.

It was a noticeable shift: Trump crossed his arms. “His whole tone changed, his whole demeanor changed. He said some things about Kim Kardashian. And at first I was like, ‘You must be talking about somebody else,’ and when I realized who he was talking about, I was like, ‘Whoa.’” (Ye mentioned Trump insulting Kardashian as well.)

After Montgomery noted that he’d appreciated Trump inviting historically Black college and university leaders to the White House as president, Trump began speaking about “some of his Black constituents that he felt didn’t thank him enough for what he did for them.”

Trump specifically mentioned rapper A$AP Rocky and basketball player LiAngelo Ball, Montgomery recalled. Both men were detained overseas by authorities in Sweden and China, respectively, during Trump’s tenure, and in both cases Trump intervened to assist the men. (Whether this actually helped is a differentstory.) 

Trump recalled “how he was talking to the other presidents of the other countries, and negotiating with them about getting them out,” Montgomery recalled. “He felt that the people that he had helped hadn’t thanked him enough.” 

“If I could do it again, I wouldn’t,” Montgomery recalled Trump saying. 

At some point after the call, Ye also asked Trump to be his running mate for 2024. Trump declined “in so many words,” Montgomery recalled, and urged Ye not to run, raising his voice.

“You can’t win!” Trump yelled at Ye, Montgomery recalled. “I have a base of 125 million people! You can’t win.” Trump looked at Fuentes, urging him, “You’ve got to tell him the truth, you’re a smart guy, you’ve got to tell him the truth that he can’t win!” He told Giorno, “Yeah, you’ll get consulting fees off of this, but you’ve got to tell him the truth that he can’t win!” 

‘I Didn’t Mince Words’

It was only after the dinner that Montgomery was able to research Fuentes and Yiannopoulos, he said.

“I’ve fought against those kinds of people and that ideology for my entire adult life,” he said. In a tweet a few days after the dinner, he called out police in Shreveport, Louisiana, for not stepping in when in 2020, “ARMED Neo Confederates and Neo Nazis came across the street and snatched signs and berated our demonstrators.”

I’ve fought against those kinds of people and that ideology for my entire adult life.Montgomery

“I have family members who fought against Nazis,” he said later. “I fight against Nazism.” 

Learning about Fuentes’ and Yiannopolous’ views was disappointing, he said. Referring to the white nationalist rally in Charlottesville, Virginia, in 2017 and the Jan. 6, 2021, Capitol riot – Fuentes attended the first and spoke at a rally on the eve of the latter — Montgomery emphasized the First Amendment’s right to peaceably assemble. “The challenge is when one group decides that one group has the right to exercise that right, and another group does not.” 

And what about Ye, who had already publicly promoted antisemitic conspiracy theories before the Mar-a-Lago dinner?

“Ye’s very well aware of how I feel. I didn’t mince words,” Montgomery said, adding that he told the rapper, “anything that does not unite this country, that seeks to divide, that seeks to treat people as if they’re less than others, is not of God.” 

He declined to detail his conversations with Ye further, including whether or not the two have spoken since the dinner. He said Thursday night that he hadn’t seen Ye’s appearance a few hours earlier on far-right conspiracy theorist Alex Jones’ Infowars program. Asked if he would respond to quotes from Ye praising Hitler and the Nazis, Montgomery said he’d prefer to watch the program himself, “and get full context.” 

He veered into a discussion of history, including that of slave-owning U.S. presidents who are still celebrated today; and Belgium’s King Leopold II, whose bloody colonial reign resulted in the deaths of millions of Congolese people. The United States, he said, should confront the evils of slavery, Jim Crow laws, mass incarceration and the economic disenfranchisement of African Americans as a “permanent underclass.” 

“If we’re going to fight against evil, we cannot be selective,” Montgomery said.

He added separately, “Ye is his own man, with his own thoughts, with his own words that he’s going to be responsible and accountable for.”

Still, Montgomery has appeared to defend Ye at times, even after the superstar made numerous antisemitic remarks. Montgomery has said Ye and NBA player Kyrie Irving were “financially lynched.”

In an Instagram video on Nov. 4, Montgomery referred to Ye and Irving: “We’re holding these men responsible for their words as if they’re the most educated individuals of our group, as if they intentionally said these words to be offensive. It’s unfair to go after these men’s character, and calling them antisemitic.” He later urged people to “come to the table in good faith,” but asked, “why is this even an issue in the first place? It’s an athlete and an entertainer.” 

A few days prior, on Oct. 25, Montgomery said that while many people were upset with Ye, “I’m not one of them.” He added, “With all of the quote-unquote cancellations that are going on right now, it’s only proving his point that, here it is, you can offend this group of people, and these are the consequences.” 

In the same video, Montgomery noted the common response to Ye’s comments: That he should simply call out individual people who’ve screwed him over in business deals. But if Ye only went after specific people, Montgomery said, “well, there’s going to be others who sit there and defend that individual. People who are colluding and utilizing their power against Kanye West. And we, as Black people, we should not be abandoning our brother.”  

Asked Thursday about that video, and whether Ye should have called out individuals rather than an entire religion, Montgomery said, “He could have did a number of things. But he chose the route that he decided to choose.”