On one of the calls, Trump thanked Ramaswamy for being positive about him while other Republican candidates are critical of him, according to two people familiar with the conversation, who like others spoke on the condition of anonymity to describe private talks.
The mutual praise highlights an unusual dynamic in the 2024 race between two candidates who have a vested political interest in cozying up to each other at times.
For Ramaswamy, a millennial entrepreneur trying to break out of a crowded pack of long-shot contenders running on a pitch to carry the mantle of Trump’s agenda into the future, such gestures appear aimed at winning over past supporters of the former president.
For Trump, the dominant polling leader in the race, elevating Ramaswamy complicates the path of Florida Gov. Ron DeSantis, who is competing for similar voters and has been seen this year by many in Trump’s circle as his biggest threat, even as he has fallen well behind in the polls.
How long the friendliness will last is an open question, and already there have been signs of erosion. When asked for comment for this story, Trump campaign spokesman Steven Cheung pointed to a recent social media post from Trump adviser Chris LaCivita, linking to an article highlighting Ramaswamy’s suggestion that Trump made a “false promise” on repealing Obamacare. “Here’s a guy itching to be punched and it’s not even Friday,” LaCivita wrote. At the first Republican debate in August, LaCivita said that “Vivek had the best night” of any of the candidates onstage.
At last week’s second Republican debate in California, which Trump skipped, Ramaswamy praised Trump but argued he was better equipped to carry his movement into the future. “I think Trump was an excellent president. But the America First agenda does not belong to one man,” Ramaswamy said at the debate, which Trump skipped. “I will respect Donald Trump and his legacy, because it’s the right thing to do. But we will unite this country to take the America First agenda to the next level.”
In an interview this summer, Ramaswamy said that he has seen Trump in Iowa “a couple times” since they spoke at a National Rifle Association meeting in April. Ramaswamy said he has spoken to other candidates including former vice president Mike Pence and North Dakota Gov. Doug Burgum more in the same period, both of whom have overlapped with Ramaswamy at multicandidate events that Trump typically skips. The Pence and Burgum campaigns did not respond to a request for comment.
“I mean the total number of minutes I’ve talked to him, we could probably count on one hand,” Ramaswamy said of Trump. “I think we mostly follow, each other, what we say, from public statements.”
Ramaswamy has also called DeSantis to wish him well during the hurricane and has spoken by phone with Miami Mayor Francis Suarez, the first candidate to drop out of the race, according to a person familiar with the conversations. The DeSantis and Suarez campaigns did not respond to a request for comment.
But Ramaswamy’s relationship with Trump has been one that has captured the attention of rival campaigns and other Republican operatives. “I don’t understand the strategy behind ‘I’m just going to run to praise the person I’m running against.’ It makes no sense,” said David Kochel, a longtime Republican consultant who has been critical of Trump. “It’s completely bizarre.”
A 2021 dinner set up by Jared Kushner
The Trump-Ramaswamy relationship dates back to 2021, after Trump’s son-in-law Jared Kushner arranged a dinner to introduce them, according to people familiar with the meeting.
As Ramaswamy traveled the country promoting his book, “Woke, Inc.: Inside Corporate America’s Social Justice Scam,” he made a stop by Trump’s golf club in Bedminster, N.J., to meet the former president for the first time.
Kushner — a friend of Ramaswamy’s — thought Trump would like the first time author, according to a person familiar with the relationship. In the interview, Ramaswamy recalled he and Trump discussing politics in his home state of Ohio during the meeting. Ramaswamy said that Trump asked his opinion of the various candidates running for U.S. Senate in the state, and that Ramaswamy praised J.D. Vance, a former classmate of his in law school who went on to win the seat last November. They did not talk about his own political aspirations at the dinner, according to Ramaswamy.
Trump’s intellect “exceeded my expectations,” Ramaswamy said, citing his “memory and command over specific details relating to his foreign policy record and tenure in office” and affable personality while greeting guests on the deck at the club.
“He kept commenting on my energy. I was like, ‘Actually, I thought you had a lot of energy too,’” Ramaswamy said.
Ramaswamy said he was not close friends with Kushner, whose brother Josh Kushner overlapped with him as a student at Harvard, and that he had only ever met Jared Kushner two or three times.
The other person familiar with the relationship described a closer dynamic and said Jared Kushner and Ramaswamy had spoken often before Ramaswamy announced his campaign. The two men have not been in contact since he launched his campaign, according to Ramaswamy and this person.
‘My most important adviser and mentor’
Ramaswamy launched his campaign in February and says he is in agreement with Trump on more than 90 percent of policies but that he could better move forward on accomplishing them and uniting the country, even as he has embraced extreme and polarizing ideas of his own, such as raising the voting age to 25 unless certain conditions are met.
“The donor class and the Republican Party does not like Trump. And they don’t like it when other candidates say good things about Trump, and that puts other candidates on a tight leash,” Ramaswamy said in the interview. “What runs through the undercurrent of the Trump movement is a form of nationalism, and I share that nationalism.”
Ramaswamy told reporters last month that his most recent conversation with Trump occurred “at or around the last debate” in Milwaukee, where he was the first on the stage to raise his hand to signal he would support the former president as the nominee if Trump is convicted on felony charges, and drew praise from Trump in a social media post. He did not say where or how the two communicated, but Trump was not present at the debate. A person familiar with the calls said the two have not spoken since before the first debate.
Ramaswamy says that if he becomes president, he would lean on Trump’s advice and look to him as “my most important adviser and mentor.” DeSantis recently suggested that the former president should not run again, telling CBS News that Trump is a “dealbreaker” for too many voters.
Others in the field have offered blunt criticism of the former president’s actions, including Pence, who has suggested Trump is no longer qualified to be president given his actions on Jan. 6, 2021. Haley, Trump’s former U.N. ambassador, said at the first debate, “We have to face the fact that Trump is the most disliked politician in America.”
Tricia McLaughlin, communications director for the Ramaswamy campaign, said in a statement, “Only in an industry as broken and uninventive as political consulting would the idea that attacking Donald Trump pass as a viable strategy to the nomination. These jokers recycle the same bad advice to candidates each cycle.”
Still, Ramaswamy draws distinction from Trump in some specific areas. He argues that he is the only true outsider in the race now that Trump has served in the White House, and that as a result he is more in touch with the grass roots and not distracted by “meritless” lawsuits and indictments.
Ramaswamy hasn’t shied away from attacking his other rivals. During the first Republican debate this summer, he told Haley: “I wish you well on your future career on the boards of Lockheed and Raytheon,” as the two sparred on the debate stage over Ukraine policy. He and Pence have also clashed, with the former vice president calling Ramaswamy a “rookie” and Ramaswamy recently attacking Pence for pushing a return to traditional conservative values, saying that candidates like Pence “awoke from deep slumber to realize the world and what voters care about isn’t what it was 40 years ago.”
Craig Robinson, an Iowa-based GOP consultant, described Ramaswamy’s strategy as a “great little play for now,” but questioned its long-term efficacy.
“It only moves you so far,” Robinson said. “Are you playing to be his vice president pick? Or [for a] cabinet position or whatever? At some point you’re still running against Trump, and you’re going to have to make that case.”
Trump campaign calculations
Trump and his allies have said they are happy to have Ramaswamy in the race and don’t view him as a threat. Instead, they view him as useful in the primary as someone defending him, according to two people close to the former president or his campaign. Ramaswamy also contributes to a crowded GOP field in which candidates have struggled to emerge in the polls as a clear Trump alternative.
“He likes that Vivek stands up there and praises and defends him and thinks he has some talent,” said one of the people.
Trump has praised Ramaswamy repeatedly in public comments. When asked by conservative talk show host Glenn Beck about a “Vice President Ramaswamy,” Trump responded: “He’s got good energy, and he could be in some form of something,” adding “he’d be very good.” Trump has subsequently suggested he would not pick a running mate from the current field.
In response to Ramaswamy’s declaring Trump the best president of the 21st century, Trump wrote on social media that, “This answer gave Vivek Ramaswamy a big WIN in the debate because of a thing called TRUTH. Thank you Vivek!”
With Trump skipping the debates so far, another person close to the Trump campaign said Ramaswamy fills a useful purpose as sort of a proxy for his ideas.
In addition to his public praise for Trump, Ramaswamy has led the call for his rivals to commit to pardoning Trump should any of them defeat him in the election and take the White House — even appearing outside the courthouse in both Miami and Washington on the days of Trump’s arraignments there.
“Without Trump being on the stage, he does a pretty … good job at taking up a lot of the space that Trump would normally take up,” said the person close to the Trump campaign.