In addition to feeling socially out of place, DeSantis said that Yale’s political climate was a “major, major culture shock,” noting that Yale marked his first time encountering “unadulterated leftism.”

“I am one of the very few people who went through both Yale and Harvard Law School and came out more conservative than when I went in,” wrote DeSantis. “If I could withstand seven years of indoctrination in the Ivy League, then I will be able to survive Washington, D.C.” 

According to DeSantis, experiences at Yale would later shape his political ideology. The overly liberal campus “allowed [him] to see the future,” he said — one where he now shapes Florida’s educational policies. 

As governor, DeSantis has signed state legislation restricting how concepts such as systemic racism can be taught in core classes at public universities. In March 2022, DeSantis signed the Parental Rights in Education bill, which prohibits classroom instruction on gender identity or sexual orientation in kindergarten through third grade or if not considered “age-appropriate.” 

Are DeSantis’ claims of a “militant left” at Yale an “anachronism”?

DeSantis’ time as an undergraduate history major — from 1997 to 2001 — marked a distinctly tame period for political discourse at Yale, according to Paul Freedman, who was the director of undergraduate studies for history in 2001.

Freedman, who self-describes as a left-leaning historian, did not agree with DeSantis’ characterization of Yale’s political climate. He stated his confusion with the “militant left” the governor described.

“1997 to 2001 was not an era of major controversy,” Freedman said in an interview with the News. “This is before 9/11. It’s before the invasion of Iraq. So it’s not as if the campus was divided by some political issue, as to some extent would be the case after the invasion of Iraq. It was also well after the fall of the Soviet Union and any renewed controversies about the Cold War. So I don’t think those sentiments really existed by the time DeSantis came.”

To the extent that there were left-wing undergraduates at Yale at the time, Freedman said their main cause was focused on organizing a graduate student union. Yale’s graduate student union did not win recognition until last year.

Freedman added that, while the graduate student unionization efforts drew many left-leaning undergraduates, he would “definitely not” describe their demonstrations as “militant leftism.” 

“I’m not sure I can imagine what the ‘militant left’ would be at that time, as opposed to say, during the Vietnam War or the aftermath of World War II,” he said. “There’s a certain anachronism about all of this.”

Conservative undergraduates, specifically within the history major, have always been a minority, Freedman said. But he described those students as an “articulate, well-organized, not tiny” minority. The same is true for most elite universities, Freedman said, specifically citing Harvard and Brown.

According to a 2017 News survey of University faculty, nearly 75 percent identified as “liberal” or “very liberal.” By contrast, 7 percent of faculty described themselves as “conservative,” with only 2 percent identifying as “very conservative.”

“There always was this kind of esprit de corps of conservatives here, because they were a minority, but a proud minority with a long tradition,” Freedman said.

At the turn of the millennium, the Republican Party was the “country club party,” Freedman said. He added that it was the party of elites and many Yale graduates.

Even if the University’s population was liberal at the time, many of its most prominent alumni were not. Freedman pointed to the Bushes — George W. ’68 and George H.W. ’48 — both of whom graduated from Yale and were members of the Delta Kappa Epsilon fraternity, as was DeSantis, before going on to become American presidents.

He added that the dimensions of offensive elitism and militant leftism which DeSantis has used to describe his time at Yale reflect a “21st-century sense of injustice and exclusion” that did not yet exist in the late 1990s. 

“It was a liberal campus for sure,” Freedman told the News. “But that is not what DeSantis is claiming. His attitude isn’t ‘I felt lonely because I wasn’t a liberal.’ It’s ‘I felt outraged because they were tearing down my country.’ Certainly that wasn’t true, at least among the faculty.”

Politics in the classroom 

At an event with the Republican Jewish Coalition earlier this year, DeSantis criticized the content taught in his Yale classes. 

Though there were many liberal students who were opposed to Bush, Noriega said that on campus there were “a lot of conservatives that supported him too.” 

Nick Sinatra ’03 — DeSantis’ close friend and former fraternity brother who has donated to his presidential campaign — also said that the political climate at Yale at the turn of the century was heavily left-leaning.

“It was very liberal for sure,” Sinatra told the News. “I’m sure it’s no different than it is now. If anything it’s probably more liberal now.”

Sinatra said he first felt political tensions on campus in the lead-up to the election of 2000. He described the election as the first time he felt the “great divide” in the country.

According to Sinatra, politics were not a constant feature of campus discourse in the early 2000s. He added that before Sept. 11, 2001, he did not remember students’ political conversations being emotionally charged.

“We’ve got this crazy divide now, but I think back then, it wasn’t so personal,” Sinatra said. “It’s gotten more personal over the years.”

In the lead-up to the 2000 presidential election, Sinatra was in the minority of Bush supporters on campus, he said. He was involved with the Yale College Republicans in supporting the Bush-Cheney ticket that year. According to Sinatra, DeSantis was not part of any political group on campus. 

Sinatra remembered the College Republicans, while nowhere near as large as the Yale College Democrats, as a “pretty substantial group” that met regularly and distributed flyers on campus.

Like Eire and Freedman, he recalled the professors skewing heavily liberal. But for the most part, Sinatra said that he never felt that any professors were “outspoken” about their views or that classes were heavily imbued with political rhetoric.

He said that “militant” — the word DeSantis used to describe Yale’s liberal population — was a stronger word than he would use.

He said that at times engaging with Yale’s overwhelmingly liberal population led to productive discourse — it helped him learn from the other side and hone his own political views.

“As somebody who was on the other side of the fence, I didn’t find [Yale] offensive,” Sinatra told the News. “I appreciated the friendly debate around politics when I was there. I learned from the other side, in terms of how they viewed things, and that sharpened my views of things on the more conservative side of the aisle.”

“Fish out of water” or an “odd bird”? 

DeSantis has publicly described his feelings of political alienation at Yale, comparing himself to a “fish out of water.” According to Noriega, a fellow member of St. Elmo Society, this alienation might have been more about personality than politics. 

Noriega described DeSantis as an “odd bird,” a consensus she said was shared by several women in St. Elmo. 

Noriega found out about DeSantis’ successful run for governor in Florida through article links that were shared in a Facebook group chat with other St. Elmo Society alums. 

Her initial response was shock.

Noriega has previously spoken on DeSantis’ character for a New York Times article. She and two other St. Elmo members detailed how DeSantis rolled his eyes and seemed “bored and disinterested” when she shared her experiences as a Latine woman growing up in San Antonio. DeSantis’ spokesperson told the Times that it was “frankly absurd” for one to remember “such a detail from decades ago.” 

For Noriega, her perception of DeSantis has remained firm in her memory due to his “standoffish” behavior throughout their senior year.

“That’s why I remember him so well,” said Noriega. “I don’t remember a lot of details, but I remember how he made me feel. There’s other people in society that I don’t have any concrete memories of at all, because they were friendly, but we didn’t stay in touch. But I remember him because I was like, ‘What is it with this guy? You know, there’s something off about him.’”

She said she did not view DeSantis’ depiction of Yale as an elitist campus as necessarily accurate. Noriega said that most Yalies were “a part of the mix” and she was surprised by the diversity of Yale. 

While students who had alumni parents and came from private schools were present while DeSantis was a student, they made up a minority of his graduating class, according to a Yale University Fact Sheet for the class of 2001. 

Forty-six percent of the class of 2001 came from independent schools, while 54 percent graduated from public high schools. Fourteen percent of DeSantis’s peers were legacy students.

“Yes, there were the Andover-Exeter kids,” said Noriega. “I had come from a public school in San Antonio, so that was very foreign to me, too. But there were plenty of other people from diverse backgrounds … The thing about Yale that struck me was how diverse it was. San Antonio, Texas, is predominantly Latino, it’s kind of homogenous in that sense. When I went to Yale, there were people from everywhere and all different races and everything like that.”

Noriega knew very little about DeSantis as a Yale student, other than the fact that “baseball was a big thing for him,” she said. According to Noriega, he would arrive at the weekly St. Elmo meetings wearing his baseball uniform. 

Sinatra first met DeSantis when he was a first year and DeSantis a junior. Sinatra’s first-year roommate was on the baseball team and would often invite his teammates over to watch sports games. 

On the day Sinatra met DeSantis, the governor was among a group of baseball players eating pizza and watching wrestling in his common room. Over time, it became something of a ritual — Sinatra recalled there being many times when he would order food and watch games with DeSantis and his baseball teammates. The two remain friends today, according to Sinatra.

Sinatra said DeSantis was quiet and studious as an undergraduate. Sinatra said he remembered DeSantis darting around campus with a backpack full of dense history textbooks.

Throughout its nearly 200-year existence, Yale’s DKE chapter has been at the epicenter of many controversies. DKE’s hazing practices — which include a seven-day “Hell Week” during which members allegedly beat pledges with hangers and smeared them with condiments — made national headlines in 2000. 

When Supreme Court Justice Brett Kavanaugh ’87 LAW ’90 — a member of DKE — was accused of sexual assault in 2018, scrutiny of Yale’s chapter entered national discourse. A 1985 photo of DKE members waving a flag made of women’s underwear resurfaced as the group was saddled with accusations of misogyny and sexual assault. 

In 2018, following allegations of sexual assault, the fraternity suspended all social activities. DKE then lost its lease and was effectively inactive for four years. In the spring of 2022, the fraternity publicly returned to the undergraduate social scene.

According to Sinatra, DKE in the early 2000s was mainly, but not exclusively, composed of athletes. He said it was a 75-25 ratio of athletes to non-athletes. Baseball players, football players and lacrosse players comprised the fraternity’s athlete population, according to Sinatra.

Sinatra lived in the DKE fraternity house during his junior year. He described it as a space where members would study and socialize “a bit” during the week, but spend a lot of time socializing on the weekends.

He said membership in the fraternity was akin to a “brotherly connection.” While some members turned to DKE as their main social outlet, others were less involved, Sinatra said.

“On the weekends, you had people coming through and hanging out, ordering pizza and watching football games or baseball games,” Sinatra told the News. “I think people joined DKE for that reason, you know, for that sense of strong relationships formed through doing activities together. It was a chance to be part of an organization that’s bigger than yourself.”

Sinatra described DeSantis as “the exact opposite” of an active DKE member. DeSantis was a starter on the baseball team and a diligent student, which, Sinatra said, consumed most of DeSantis’ time. 

Sinatra emphasized that he had no memory of DeSantis’ involvement in the fraternity’s Hell Week.

While he was not involved in DKE on a day-to-day basis, Sinatra said DeSantis would frequently show up to the fraternity’s weekend social events. Sinatra said that during the fall, DeSantis organized opportunities for his DKE brothers to gather and watch World Series games — gatherings that first brought Sinatra and DeSantis together in the fall of 1999.

Sinatra spoke to the general perception of athletes on campus at the time, saying they were viewed as inferior by their peers.

“I felt that athletes were generally looked down upon by a lot of professors and some students,” Sinatra told the News. “Athletic events just weren’t really well attended.” 

According to Nicole Lim ’04, who was a member of the Kappa Kappa Gamma sorority, DKE was known as “one of the jock frats.” She said that she knew DKE’s hazing process was “intense” from anecdotal information shared within her sorority. 

Though Lim said she could not remember if she ever attended a DKE party, she recalled that most of their parties were also predominantly composed of athletes.

“Yeah, I think [DKE] was like very much a football-baseball frat?” said Lim. “It had a reputation for just being a frat-y frat. It was like jocks and stuff. It was bro-y.”

The News reached out to nine members of Yale’s 2001 baseball team for comment. One declined to comment and eight did not respond. 

While St. Elmo included students from different communities at Yale, Noriega said that it drew a considerable number of student-athletes — Noriega was a water polo player who had another teammate in the tap class above her. 

In describing the student-athlete culture at Yale, Noriega said that it was common for athletes to primarily befriend and engage with their sports team, even though there was not a strict divide between students.

Funds from Bulldog teammates and brothers 

Since their time at Yale, Sinatra and DeSantis have remained close friends, and Sinatra has contributed financial support to DeSantis’ political campaigns for over a decade. 

Sinatra first supported DeSantis’ 2012 campaign for Florida’s 6th congressional district. Deciding to run after his military service in Iraq, DeSantis reached out to Sinatra, who had worked for President Bush and had previously been involved in Republican politics.

“He was looking for help trying to put together a fundraising apparatus,” said Sinatra. “I rounded up a few Yale athletes, we put some money together and did a little fundraising dinner for him in New York.”

Internally known as the “Fight Club,” the group is composed of former classmates, DKE fraternity brothers and baseball teammates who have funded Desantis’ presidential campaign — contributing nearly $5.5 million to his campaign funds so far. 

DeSantis spoke about this “Fight Club” in an October interview with Fox News.

“Some of my closest friends that I’ve had for 20, 25 years, they are killing it for me raising money,” DeSantis said to Fox News. “I mean it’s really, really cool to have guys I was in college with playing baseball that are now here as part of this.” 

Though Sinatra avowed “wholehearted” support for DeSantis’ campaign, he said he was hesitant to align himself fully with all of DeSantis’ policies. According to Sinatra, he supports DeSantis financially not because he agrees with all of his political views, but rather, because he supports his character. 

“It’s always, to me, about the person, not every single view. I’m never going to agree 100 percent with one person on every single view,” said Sinatra. “The characteristics of Ron that I love are who he is as a person. I mean, he’s a huge family man. I’ve seen him interact quite a bit with his wife and his kids.” 

At a panel with the Republican Jewish Coalition earlier this year, DeSantis said that were he to receive a resume from a Yale affiliate, he would be “negatively disposed.” 

This negative disposition, according to Sinatra, stems from the governor’s belief that the University has a political agenda. Despite his rhetoric, Sinatra said he believes DeSantis was proud of his time at Yale and the friendships that he formed at the University.  

Sinatra said that he personally appreciated his Ivy League undergraduate and graduate education. 

He told the News that he does not think he would not be where he is professionally without his Yale and Wharton degrees.

In response to DeSantis’ public depiction of Yale, Noriega said that DeSantis’ disavowal of Yale elitism was “silly.”