When Harvard was renegotiating a contract with janitors and other workers in the fall of 2005, many students pushed the nation’s oldest and wealthiest university to pay a living wage.
Vivek Ramaswamy, then a politically active biology major, led the dissent. Writing for the school newspaper, he argued that a raise would come “at the cost of respect that the rest of the Harvard community has for these workers.” And in Listserv emails obtained by NBC News, he bemoaned the student government’s involvement in the debate, citing the recently bungled planning of a Wyclef Jean concert.
“Their duty to perform these basic tasks,” Ramaswamy, now a Republican candidate for president, wrote to Ali Zaidi, then a student government official, now President Joe Biden’s top climate policy adviser, supersedes “their prerogative to make political statements on behalf of the student body.”
It was neither the first nor last time that Ramaswamy earned his reputation as a disruptive brainiac who was willing, and even eager, to dance on political third rails and challenge conventions.
That eagerness would come to define Ramaswamy at a trio of top institutions — St. Xavier High School in Cincinnati, Harvard and Yale Law School — where classmates recalled a pugnacious student who centered debate in his educational life and always seemed to push his takes past their logical endpoint.
“He was known in the class as the devil’s advocate,” one former law school classmate said. “And at a certain point, if someone is always playing the devil’s advocate, you have to kind of wonder whether he’s actually the devil.”
The son of Indian immigrants from Ohio and the product of elite East Coast institutions that make convenient foils for culture warriors like him, Ramaswamy arrived on the national scene this year as a surprise White House contender.
The 38-year-old literally wrote the book on “anti-wokeism.” He has rapped to Eminem, dabbled in 9/11 conspiracy theories and gleefully taken on a field of more traditional primary candidates all while avoiding the ordinarily inescapable wrath of former President Donald Trump.
Interviews with 29 former classmates and others who have known Ramaswamy as early as his days as a mild-mannered prep tennis player — several of whom requested anonymity for personal and professional reasons — reveal a portrait of someone who transformed into a provocateur.
Ramaswamy’s campaign did not dispute any of the details that emerged from the reporting. And in a recent interview, the candidate himself said being in the ideological minority at a place like Harvard awakened his “naturally contrarian instincts.”
The experience “honed and sharpened my own views,” Ramaswamy said after a campaign event in Ohio. “I think I got a better education because of it. I got no doubt a better education, more of my money’s worth at Harvard and Yale, precisely because a lot of my views were challenged and vice versa.”
While his worldview didn’t quite fit in with the liberals who dominated the exclusive schools he attended, classmates mostly remember Ramaswamy fondly as a fun-loving intellectual jouster full of hot takes. But his norm-smashing presidential campaign has left some of them wondering if they ever really knew the real Vivek Ramaswamy — or if there even is one.
“When I heard some of the things Vivek said, I just thought, he’s lying. I don’t think he believes this stuff,” said Alyssa King, a Harvard classmate who is now a law professor. “And he may think that what he’s doing is he’s telling some sort of noble lie, and then he’ll get power. And I don’t know what he wants to really do with it, because I don’t think he knows.”
Or as another Harvard classmate put it: “I would guess that, of the folks in my class who know him, a large chunk used to hold relatively positive views of him but now want to punch him in the face.”
Through two Republican debates this year, Ramaswamy’s rivals have received a taste of the style that has both charmed and maddened those who’ve gotten to know him over the last 20 years. At the first, Ramaswamy seemed to delight in fighting with his GOP elders. At the second debate last week at the Ronald Reagan Library in California, he invoked the former president’s commandment to not attack fellow Republicans while under fire from former United Nations Ambassador Nikki Haley — who said she feels “a little dumber” every time he speaks.
“I’m the new guy here, and so I know I have to earn your trust,” Ramaswamy said at another point. “What do you see? You see a young man who’s in a bit of a hurry, maybe a little ambitious, bit of a know-it-all, it seems, at times. I’m here to tell you, no, I don’t know it all. I will listen.”
But Ramaswamy has long stood out, even in a world of overachievers. “In a room full of people who really like to talk, he would like to talk the most,” said another Harvard friend and classmate.
After graduating as his private high school’s valedictorian, he catapulted himself to the top of America’s hyper-meritocracy and decided he liked the view.
Graduating cum laude from Harvard, he made a fortune in Manhattan finance before enrolling in Yale Law School, even though he had no need for the degree or plans to practice law. And after making a name for himself among the kinds of East Coast elites he now demonizes, he returned home ahead of launching a political career.
On the surface his rise is a familiar story, following the well-worn playbook of other young men in a hurry, several he knew from school: Transportation Secretary Pete Buttigieg (three years ahead of him at Harvard) and Sen. JD Vance, R-Ohio (same class at Yale). In moments worthy of a time capsule, Buttigieg and Ramaswamy both asked questions of Democratic presidential candidates — Dick Gephardt and Al Sharpton, respectively — on MSNBC’s “Hardball” during the 2004 race.
But even their expedited paths into public office were apparently too slow for Ramaswamy, who returned to Ohio in 2019 with his wife, Apoorva, to raise their young family. As he sniffed out a pivot to professional politics, he took a look at the kind of VFW hall-stumping and state senator ego-stroking necessary for a local run and decided his skillset was better suited for a White House bid, where attention is the coin of the realm.
“I’ll be candid. I told him he shouldn’t run for the Senate — I told him he should run for president,” Ohio Lt. Gov. Jon Husted, who is perhaps Ramswamy’s closest Republican friend in the state, said in an interview. “Because he has ideas. He’s willing to think about things differently.”
St. Xavier’s ‘annoying perfect student’
Ramaswamy was known at St. Xavier — a prestigious and private all-male Jesuit high school that requires a rigorous academic entry exam — not for his politics but for his smarts.
“Being recognized for good grades is nothing new to Vivek Ramaswamy,” read a 2002 Cincinnati Enquirer article under the headline, “Award winners serve the community.”
“Kind of the stereotype of the annoying perfect student,” said Richard Thayer, who took several advanced placement classes with Ramaswamy and recalled visiting his home to tackle a balsa wood bridge project.
“My parents always knew his name, because he was the top student in my class,” Thayer added.
Ramaswamy played varsity tennis and competed on the Science Olympiad team at St. X, as alumni call it. Classmates regarded him as friendly, but not particularly outspoken.
Mark Neyer, a fellow 2003 graduate, remembered how he often targeted Ramaswamy in a lunchroom scheme. Neyer would harass his peers for spare change so he could buy candy — usually a Charleston Chew, in his recollection — and found Ramaswamy, who was not a close friend, to be his easiest mark. On and on it went, until one day Ramaswamy, even as he again coughed up some coins, gently scolded Neyer about how annoying the behavior was.
“It was the look on his face as he was reaching into his pocket,” said Neyer, who added that he recalled thinking to himself: “Maybe it’s not worth the 35 cents.”
Ramaswamy was learning to speak up.
A ‘contrarian’ is hardened at Harvard
Far from the cafeteria at St. X, Ramaswamy found his voice in the intellectual sandbox of Harvard Yard, where he woke up every morning down the hall from the dorm room where Mark Zuckerberg, a class ahead of him, created Facebook. Across the street was Harvard’s Kennedy School, the hub of campus political life.
On Thursday nights, over takeout from a hole-in-the-wall pizzeria affectionately known as Noch’s, Ramaswamy presided as chairman of the Harvard Political Union, where he would adopt polemic positions to provoke others to debate. He often left people guessing about his true beliefs.
When a big-named speaker would come to campus, Ramaswamy “would always have a sort of flame-thrower question to try to catch them off guard,” said Jessica Montoya Coggins, a classmate who is now an editor of the progressive Texas Signal. “I remember thinking, ‘This person kind of had a way of acting and professing things that maybe they didn’t believe in, but helped them get more attention.”
There were at least four future billionaires in his class, along with at least one future member of Congress: Rep. Elise Stefanik, R-N,Y., who was a fellow officer in campus political groups. Buttigieg, another Midwest immigrant’s son who made an expectations-beating presidential run, was a few years ahead and knew Ramaswamy only casually, according to people who know them both.
A debater, op-ed writer, listserv-mailer and part-time rapper under the alter-ego “Da Vek,” Ramaswamy stood out on the mostly liberal campus for having “a reputation as being a libertarian iconoclast, but more just in for a debate,” according to a former classmate.
Ever-present at campus events and reliable with a good quote even then, Ramaswamy was a regular on the pages of the Harvard Crimson, the student newspaper.
“I consider myself a contrarian,” Ramaswamy told the Crimson for a December 2006 profile. “I like to argue.” (In the article, he also said he thought “children should be forced to listen to” Eminem’s “Lose Yourself,” a song he has performed on the campaign trail.)
He published an op-ed in The New York Times before he graduated. And he was quoted in The Boston Globe saying he didn’t mind that Harvard banned alcohol at tailgates because “the fun is what you bring to it … and I bring the fun.”
In a milieu where political ambitions were nothing to be ashamed of — several classmates had email addresses with phrases like “prez 2028” tacked on to their names — Ramaswamy was unusual in being a science major with stated career interests in business, not politics. And he remained a model student who thrived in the high-pressure environment.
“For me, Harvard has created a new home,” Ramaswamy told the Crimson for a story about a Diwali celebration hosted by a South Asian student group, in which he was involved.
And he and his friend Nicholas Green — now the founder and CEO of Thrive Market, a subscription service offering natural and organic foods — started a consulting service for high schools looking to get into top schools called IvyInsider.
“Our value proposition,” Ramaswamy said of the group’s pitch, “is that the people who can help you best are the people who have been in your position.”
An ‘intellectual vacation’ at Yale
By the time Ramaswamy applied to Yale Law School — consistently ranked among the top law schools in the nation — he had already accumulated plenty of wealth from his stint as a hedge fund manager in New York.
“He was just having this fun little intellectual vacation,” said one former classmate. “I do have a general memory of his hand going up almost every day in response to almost any question.”
“Fun” was a word that came up often in discussions with Ramaswamy’s former classmates.
He was seen as a charmer who wanted to make friends and influence people. But even in a place that trains litigators, he was also considered to be the ultimate debater, reveling at the challenge of defending the indefensible. Classmates struggled to understand whether Ramaswamy actually believed all the points he was making or if he simply enjoyed intellectually jousting.
“He was very charming and challenging to argue with in the way that it’s interesting and challenging to argue with the Unabomber,” said another former classmate.
Some of his takes at the time were seen as so out there that they still stand out to classmates years later. In 2012, one classmate recalled Ramaswamy arguing in a group discussion that a serious way for U.S. policymakers to increase engagement in democracy would be to allow citizens to buy the voting rights of others or sell their own.
Interestingly, as part of an interview last year with The New Yorker in which Ramaswamy was asked why he was not worried about the ultra-wealthy having too much influence in politics, he said, “You can buy your yachts, you can buy your houses, you can buy your nice cars, but you shouldn’t be able to buy a greater share of voice as a citizen.”
Of course, as his presidential campaign has at times highlighted, Ramaswamy isn’t afraid to test out ideas or proposals that he later tweaks or distances himself from. Asked about his old suggestion to allow for the literal buying and selling of votes, Tricia McLaughlin, a Ramaswamy spokesperson, said the candidate “doesn’t remember this, but throughout high school, college, and law school, Vivek was always open to exploring ideas that others weren’t.”
Ramaswamy’s personal wealth was well-known on campus, so much so that classmates deemed him “most likely to conduct a hostile takeover of the law school,” when assigning superlatives to the class.
“Vivek took this in good stride, largely because he was the contrarian in his Yale Law School class,” McLaughlin said.
Still, Ramaswamy chose to live with roommates — albeit, at one of the fanciest apartments available in New Haven. He wanted to hang out. He took friends to off-Broadway shows in New York. He organized dinners, often Mexican. And he was generally seen as good company. (McLaughlin described her boss as “gregarious” and someone who “enjoys people!”)
“Someone compared him to Ted Cruz,” a former classmate said of the Texas Republican senator, who as a Harvard Law student would reportedly only study with people who had attended Harvard, Yale or Princeton. “But no, I think that’s the wrong example.”
“Vivek is quite likable,” the former classmate continued. “And he was interested in making friends and jokey with people.”
At Yale, Ramaswamy developed a connection with Vance, another conservative culture warrior with an Ivy League pedigree and Ohio ties. While the two did not always travel in the same social circle as students, they would watch Cincinnati Bengals games together and stayed in touch as their careers took similar trajectories.
“Vivek was just bursting at the seams” with ideas, one classmate recalled, adding, “JD was always like, ‘I’m a Republican. That’s the end of the story.’ And I think Vivek was very much like ‘let’s think of all these different things and you don’t know what I am.”
Vance’s old roommate at Yale, Josh McLaurin, who is now a Democratic state senator in Georgia with a low opinion of Vance, has an even lower opinion of Ramaswamy.
“Unlike JD, Vivek is purely a grifter with no chance of winning,” he said. “Everyone knows the U.S. presidency shouldn’t be your first race.”
Vance, for his part, said in a recent interview with Axios that he and Ramaswamy have remained “pretty good friends” since Yale. Vance hosted Ramaswamy for Thanksgiving in 2019, and said he thinks his former classmate would make a good president, though he has endorsed Trump.
Like Vance, Ramaswamy’s old classmates are betting that Trump will ultimately win the GOP presidential nomination. Yet while some of those same classmates don’t understand his presidential campaign, they recognize the man at the center of it.
“In the same way that he spent three years of his life pursuing a degree that he was never going to use just for the fun of it, I kind of think he is running for president largely just for the fun of it,” one classmate said, adding, “The way he’s positioned himself, he’s kind of betting that Donald Trump is going to end up in jail and he’s going to be the heir apparent as the most Trumpian Trump that ever Trumped.”
Ramaswamy, for his part, has said the only purpose of his bid is “to win.”
One of the biggest struggles for his former classmates is trying to suss out what Ramaswamy actually believes versus what is a performance for the benefit of the Trumpified GOP base.
More than one active Democrat attended his Midtown Manhattan wedding. And he would often cross paths with his mostly liberal former sparring partners in the social spaces of New York City’s elite and was always friendly.
But can these friends and acquaintances, most of whom loathe Trumpism, still be friends with someone so eager to tap into the Trump movement?
“I’ve been kind of wrestling with the question of whether I would call him a friend,” one classmate said. “Because I try not to be friends with people who are, like, terrible. But he was easy to talk to. And he was thoughtful and curious. And charming. I think most people liked him.”