Move Aside Harvard and Wharton. The ‘Middlebury Mafia’ Is Taking Over Wall Street

Meet Wall Street's "Middlebury Mafia."

Incoming Morgan Stanley CEO Ted Pick, who graduated from the small Vermont college in 1990, is now at the pinnacle of the finance world. But he is not the only "Middlebury Man" breathing that rarefied air.

At the top of chief Morgan competitor Goldman Sachs sits President and COO John Waldron, Middlebury class of 1991. 

While Pick and Waldron might not have been friendly at school, they are buds today, despite steering known arch-nemeses. Multiple people who attended school with them, and others who work with them today, say that their shared time at the clubby liberal arts college in Middlebury, Vermont, provided a basis for a personal relationship that continues today. Some even wonder whether their friendship will tone down the bitter rivalry between two of the nation's most powerful investment banks.

Looking at their resumes alone, it’s not hard to see the similarities — and a few differences — in Pick's and Waldron’s college experience. The most glaring is that while both were star students, they didn't shine in finance.

Pick majored in international politics and economics, while Waldron majored in English. Both graduated Phi Beta Kappa.

“Even if you know that you’re going to be an investment banker after graduation, like I remember Waldron being,” mused one member of the class of 1991 who is now also an investment banker, '[Middlebury] is a place you go to spend four years pretending that you’re going to do something else, and that’s a very good thing.”

The Anti-Wharton

Unlike Ivy League schools, many of which are located in urban areas and all of which have large graduate schools that boost the size and median age of the student populations, Middlebury is in rural western Vermont with a total undergraduate population just over 2,700 and no MBA program.

Instead of dressing up to indulge in the buzzy nightlife of clubs and art shows that don't exist in a tiny Vermont hamlet, Middlebury students tend to drape themselves in Patagonia and sweats to play sports and enjoy the natural beauty of Northern New England.

"Midd Kids," as they sometimes refer to themselves, are typically found playing a varsity sport (27% of the student body does), hiking in the Green or Adirondack Mountains, golfing on the campus golf course, skiing down the school’s private ski slope, or skiing across its Breadloaf Nordic skiing trails.

“It’s the anti-Wharton,” said a senior asset manager who graduated from Middlebury in the early 1990s. “The people I was in school with that went on to top jobs on Wall Street might have gotten Ivy League MBAs after they graduated, but none of them studied finance while we were there. The school didn’t offer it.”

Pick, indeed, went on to get an MBA from Harvard Business School, but Waldron took a junior investment banking job at Bear Stearns after graduation and worked his way up before joining Goldman in 2000. Neither Pick nor Waldron agreed to be interviewed for this article.

Crossing (Hiking) Paths

In the early 1990s, the school was even smaller, with just over 2,000 students, and according to accounts of multiple classmates, Pick and Waldron crossed paths and had more than a few mutual friends and acquaintances.

“Everyone knew each other,” said another graduate of that era who works in private equity. “I don’t know if guys like Pick and Waldron hung out, but I knew Pick and [JPMorgan Private Bank CEO David] Frame and a lot of other people who have big jobs did. If we run into each other, it’s always nice to chat about Midd.”

In fact, a cursory look at old yearbooks reveals that not only was Middlebury playing host to a few future Wall Streeters, it was a veritable farm team of financial executive talent between 1989 and 1992. 

In addition to Pick, Waldron and Frame (also ‘91), Cross Ocean Partners CEO and former Merrill Lynch Global Credit chief Graham Goldsmith graduated in 1989; billionaire investor Frank Mosier is class of ‘91; Carlyle Partner Janine Feng and Credit Agricole’s Head of Global Markets, Kashif Zafar, are class of ‘92.

According to numerous former Midd Kids from that era who spoke to The Messenger, the closeness of the college community meant that most of those current business titans remain in touch today. They said their intimate shared college years provided a fertile training ground for how to act once they got to another infamously small world: Wall Street.

“It was the kind of place where if something crazy happened on a Saturday night, most people knew about it on Sunday morning in the dining hall,” recalled Leland Hart, class of 1991 and a portfolio manager at hedge fund Warwick Capital.

PayPal's recently retired CEO, Dan Schulman, class of 1980, returned in 2022 to give Middlebury's commencement speech. Admitting he wasn't always the best student, Schulman said he learned a lot from "playing sports on these fields, from friendships I made on the campus."

New Recruits

While Pick and Waldron might be the biggest Middlebury names on Wall Street today, they could soon be facing some stiff competition.

Blackstone Co-COO Anthony Civale is class of 1996, and Blackstone Private Equity COO A.J. Murphy is class of 1998. Brian Deese, former Global Head of Sustainable Investing at BlackRock and former director of the White House National Economic Council, is class of 2000.

(Full disclosure: This reporter is class of 2002.)

Until those names begin to move up higher on management team rosters however, Pick and Waldron will remain the top Midd Kids, perhaps bringing a thaw to one of Wall Street’s frostiest rivalries.

“In the end, they’re both Middlebury men,” quipped the alumni investment banker. “I’d expect they’ll be much more collegial while trying to cut each other’s throats.”

But that doesn’t mean everyone will get off easy.

“Someone should tell [Goldman Sachs CEO David] Solomon that Waldron and Pick are almost certainly making fun of him behind his back for going to Hamilton [College],” joked the alum asset manager. “Unless they’re doing it to his face.”