Contrarian to the Core: President Mark Roosevelt's Enduring Legacy

Roosevelt retires this summer after serving for nearly nine years as St. John’s collegewide president.

June 6, 2024 | By Kerri Braly

When Mark Roosevelt retires in June after nearly nine years as collegewide president of St. John’s College, his legacy will include a landmark tuition reduction, a campaign that raised $326 million, a stronger support system for students, and a more secure future for the school’s distinctive academic Program. 

Outgoing St. John’s President Mark Roosevelt

He will also be remembered as a self-styled contrarian who came to St. John’s as an outsider but led as a kindred spirit.

“One of the through lines in Mark’s career and character has been this need to fight for the underdog,” observes J. Walter Sterling (A93), a longtime tutor and former Santa Fe dean who will succeed Roosevelt as president of the Santa Fe campus. “That holds with his earlier work as a legislator, his work with the Pittsburgh Public Schools, and at Antioch College, which he reopened. In all of those cases, he came into adverse circumstances that required leaders who believed in and were willing to fight for the cause.”

By the time Roosevelt arrived in 2016, St. John’s was more than just an underdog in higher education. The college had struggled to adapt to the financial challenges and demographic shifts that followed the Great Recession of 2008, including a drop in the number of college-bound students and, most importantly, a steep decline in students’ ability to pay for college. As a result, St. John’s found itself grappling with a structural deficit that amounted to more than 20 percent of its annual operating budget. Meanwhile, tuition had risen to $52,000 (or $68,000 when adjusted for inflation) at a time when families were signaling their inability to accommodate higher prices.

Pam Saunders-Albin (H15), Vice Chair of the Board of Visitors and Governors, recalls Roosevelt’s first Board meeting, when he immediately positioned himself as a truth-teller who wasn’t afraid to sound an alarm on harsh realities facing the college. “He was breathtakingly honest,” she says, “candidly telling us we needed to take off our rose-colored glasses, that we weren’t on a financially sustainable course.” Placing their faith in Roosevelt, the Board appointed him to the newly created role of collegewide president, giving him authority over the college’s finances. Empowered, he worked to centralize the school’s administrative structure, eliminating redundancies and creating collegewide departments that served both campuses.

These changes, including personnel cuts and salary freezes, could have dampened morale. Yet something quite different happened: staff and faculty gained confidence that the college’s problems could be overcome and its future secured. Morale was further boosted by journalist Frank Bruni’s New York Times article, which extolled the virtues of a St. John’s education.

“Mark saw that we had to make changes in how we operate, but he always believed we would get out of the hole we were in while preserving what we have that is unique and special” explains Board Chair Warren Spector (A81). “That confidence inspired others to step up and say, ‘I’m going to help you get there.’”

By 2018, St. John’s had taken bold steps to regain its financial footing. The college lowered tuition by a third, approved a plan to eliminate the structural deficit, switched to a financial model that emphasized philanthropy, and launched the “Freeing Minds” campaign, highlighted by two $25 million gifts from Spector and then-Board Chair Ron Fielding as well as a $50 million matching gift from the Winiarski Family Foundation.

The campaign ultimately surpassed its $300 million goal ahead of schedule, concluding in June 2023 with $326 million raised from more than 7,300 donors. These funds have allowed the college to increase financial aid, invest in campus improvements and other critical needs, and grow its endowment, which generates a stream of annual income to help offset shortfalls in student-derived revenue.

Roosevelt, himself, was a passionate and prolific fundraiser who prioritized seeking funding for projects that increase the academic, social, and career support available to students. Through his efforts, the college established the Office of Personal and Professional Development in Santa Fe, expanded the Career Development office in Annapolis, and secured a campaign gift that guarantees every student at least one paid internship.

Recognizing that first-generation college students and students from low-income families and underrepresented communities are more likely to withdraw from St. John’s, Roosevelt also found ways to make the college more accessible and inclusive. His work with the Jay Pritzker Foundation led to the $10 million Pritzker Promise, which matches a student’s Pell grant, effectively doubling the financial support available to those with the greatest need. That same gift funded the launch of a summer bridge program designed to help first-year students adjust to the rigors of the college, with a focus on students whose backgrounds could leave them more prone to feeling alienated or overwhelmed.

“There has long been this sense that you land at St. John’s and are dropped into the deep end of the pool,” observes Santa Fe Dean Sarah Davis. “It’s true that every class is a risk, and we want to preserve that—because there’s a beauty in it—but preserve it within a framework where people don’t feel alone.”

By strengthening what he called the “scaffolding that supports the Program,” Roosevelt also helped mend relationships with alumni who had long voiced concerns about what they saw as an unsupportive environment. “I think alumni are feeling like they can engage with the college in a more satisfying way because their concerns are being addressed, and there is evidence that leadership is listening,” says former Alumni Association President Tia Pausic (A86), who now serves as one of three alumni-elected representatives on the Board.

“When I hear stories about the state of the college in 2016, I cannot imagine what St. John’s was like for our female students and students of color, or for students who needed additional support,” adds Annapolis President Nora Demleitner, who will become the second collegewide president of St. John’s College upon Roosevelt’s retirement. “Mark really listened to what alumni and students were saying, and the conversations we have been having ever since are going to continue.”

Still, Roosevelt wasn’t a Johnnie, and some still feared he would attempt to determine which books are read at St. John’s or change the way classes are held. Others thought his surname was simply too synonymous with the status quo. How could a great-grandson of President Theodore Roosevelt, that quintessential figure of American bravado, appreciate the quirky, countercultural ethos of St. John’s?

“He’s a Roosevelt who went to Harvard Law School, so it seemed natural to me that his definition of success would be the usual one,” says Avi Dugginapeddi (A21), now a Stanford Law graduate student, who spent his first two years at St. John’s on the Santa Fe campus. “I had convinced myself that the career prestige I was seeking was for some noble cause, and he surprised me by pushing me to scrutinize that assumption, saying ‘Avi, there is more to life than that. There are other things you need to care about.’”

Roosevelt’s understanding of the Program as something more meaningful and more fundamentally human than an alternative route to conventional ends resonated deeply with the college’s mission, Davis explains. “I think that Mark, in part because he’s not a Johnnie, has a very humanistic take on the Program. It’s about the texts and the ideas, but it’s also about life and how we spend our brief time in this world. He really has figured out the preciousness of what we’re doing in terms of allowing people to follow their own path … and that approach is very true to our mission in terms of the soulful education we hope this is.”

At the same time, Sterling adds, Roosevelt didn’t try to oversee the curriculum, trusting the faculty to be stewards of the Program. “He never tried to make decisions about the content of the Program, and yet he speaks more stridently than any president in the past 20 or 30 years about how different we are and how unapologetic we should be about that.”

This commitment to the college’s distinctive identity was rooted in an appreciation for the qualities that make St. John’s unique in higher education. According to Board member Karen Pritzker, whose son graduated from the Santa Fe campus, “Mark’s charismatic and visionary leadership has helped more people to see that a St. John’s education is truly essential in these times. The Program not only models civil discourse, which is important in its own right, but also shows that it can be taught … and there is such a dire need for that.”

Carol Carpenter, Vice President of Communications and Marketing, echoes this sentiment, noting that “Mark was adamant that we always remain true to our contrarian nature, our rigor, and our devotion to free and open dialogue. At times that meant walking a tightrope across a widening political divide, pushing more conservative community members to consider the importance of diversity and belonging, while also challenging more progressive members to think critically about intellectual diversity and the consequences of its decline. Navigating those conversations, as he did, takes moral courage.”

Although Roosevelt’s willingness to engage audiences across a spectrum of views was controversial to some, others saw it as a demonstration of just how well he understood his mission to lead “the most contrarian college in America” and the fervor with which he held that responsibility. “I don’t think we have always given him enough credit for his freedom of spirit, and we should, because independent mindedness is something we value,” Davis says. “Mark embodies an actual independent spirit, and I don’t think I really knew or appreciated that to the extent that I do now.”

It was his “independent spirit” that proved invaluable for a president tasked with the duty of protecting and preserving the college at what Sterling describes as a time of tremendous change and adversity. “When conditions are eroding, you could say the practical challenges are the real threat, but in another sense, the threat is that we lose faith,” he says. “We decide, well, this kind of education isn’t relevant. The world has moved on from this. Addressing the practical challenges enabled us to reaffirm with conviction that what we do here is objectively good—for our students, for American higher education, and for the world.”

As they prepare to assume their new roles, Demleitner and Sterling admit they still see many more challenges on the horizon, but they are equipped with resources –and breathing room—they would not have had in 2016. “Mark Roosevelt launched Walter and me on this journey,” Demleitner says. “And he certainly turbocharged the start.”

He did it, both agree, in the most Johnnie of ways: through respectful conversation and a willingness to put the needs of the college ahead of his own. In one of his final acts as president, Roosevelt requested that gifts recognizing his retirement be directed to a fund established to enhance tutor salaries. This seven-year initiative, which has already raised $8 million toward a $10 million goal, will provide for a total salary increase of 18 percent for faculty.

“You know, it might be right that we’ve not had a president who was less of a Johnnie in the sense of being fluent in the inner workings of the Program and the classroom here,” says Sterling. “And at the same time, I don’t think we’ve ever had a president who fought harder to secure a brighter future for St. John’s College. That is going to be Mark Roosevelt’s legacy.”