A Controversial Dean's Departure From Yale Law

Dean Ellen Cosgrove, at the center of many recent YLS scandals, is retiring.

Yale University (photo by Markus Leo on Unsplash).

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On Tuesday, Dean Heather Gerken of Yale Law School announced the retirement of Associate Dean Ellen Cosgrove, who led the school’s Office of Student Affairs (“OSA”). As you may recall, Cosgrove and the OSA figured prominently in several YLS controversies covered in these pages, most (in)famously Trap House-gate.

In a Washington Free Beacon article fittingly titled “‘Trap House’ Dean Retires From Yale Law School,” Aaron Sibarium helpfully summarized some of the scandals:

Cosgrove’s seven-year tenure has been controversial. Along with Yale Law School diversity director Yaseen Eldik, Cosgrove hinted to second-year law student Trent Colbert that he could face disciplinary consequences if he didn't apologize for inviting classmates to his “trap house,” a term she and Eldik characterized as racist. Without an apology, Cosgrove implied in a September meeting, Colbert might have trouble with the bar exam’s “character and fitness” investigations, which she could weigh in on as associate dean. The law school found itself doing damage control after the Washington Free Beacon published audio of the meeting—and after figures across the political spectrum slammed Cosgrove and Eldik for chilling free speech….

It was one of three scandals to beset Cosgrove over just the past year. In November 2021, Cosgrove, Eldik, and Gerken were hit with a lawsuit alleging that they retaliated against “two students of color” for refusing to make “false statements” about Amy Chua, a professor who has repeatedly ruffled the administration's feathers. And in March 2022, Cosgrove looked on as hundreds of student protesters disrupted a bipartisan panel on civil liberties. The protest was a “blatant violation” of the law school's free speech policies, according to Kate Stith, the professor moderating the panel, and caused so much chaos the police were called.

Not surprisingly, Dean Gerken’s email announcement mentioned none of this:

I write to share the news that Associate Dean Ellen Cosgrove has decided to retire after a 27-year career in student affairs. I want to thank Dean Cosgrove for her years of service to generations of students at Yale, Chicago, and Harvard.

Dean Cosgrove received YLW+’s Staff Excellence Award in 2017. On a national level, she served on the Boards of the Association of American Law Schools Student Services Section and the National Association of Law Student Affairs Professionals. She has advocated for law student mental health through her work on ABA, Connecticut, and Massachusetts Bar committees.

Dean Cosgrove’s last day at the law school will be August 12. During this time, we will begin a search for the next Associate Dean of Student Affairs.

And no, I’m not interested. Being a law school administrator today sounds super-stressful, plus I don’t think I’m very popular at YLS right now.

But neither is Dean Cosgrove, and her departure doesn’t come as a shock. I suggested back in November that Cosgrove might be ousted, and before Dean Gerken won reappointment, she made clear—to faculty, alumni (including wealthy donors), and others who weren’t Cosgrove fans—that Cosgrove wouldn’t be part of the core team in a second Gerken term. In fact, removing or reassigning Cosgrove was considered to be a “campaign promise” of Gerken as she sought renewal.

It makes sense, though, that Cosgrove retired on her own instead of getting fired—and even received a generous severance package to encourage her departure, according to word around 127 Wall Street. (I reached out to both Yale Law’s spokesperson and to Cosgrove for comment; YLS declined comment, as it typically does on personnel matters, and Cosgrove didn’t respond.)

Why wouldn’t Dean Gerken simply fire Dean Cosgrove? First, Gerken doesn’t like confessing error—just look at her messaging over the past year, which continues very little self-blame—and firing Cosgrove could have been construed as an admission that mistakes were made.

Second, Cosgrove is both a key player and witness in Stubbs v. Gerken, the unpleasant lawsuit two students filed against Yale Law, Gerken, Cosgrove, and YLS diversity director Yaseen Eldik. Canning Cosgrove could be read as an admission that she did something wrong, and it also could cause her to become unhelpful or even hostile to the law school in that still-pending litigation. (My guess is there’s a severance agreement requiring Cosgrove to cooperate in the lawsuit and requiring Yale to provide her with a defense or to cover her legal costs.)

Third, even beyond the lawsuit, firing Cosgrove could get messy. I previously described Cosgrove as “the Littlefinger of the YLS kingdom” because, just like that shrewd, manipulative courtier from Game of Thrones, she’s “a canny operator with all sorts of dirt to spill.” (The severance agreement presumably includes strong non-disclosure and non-disparagement provisions.)

Cosgrove’s quiet retirement is good news for Cosgrove and Gerken, but is it good news for YLS? While Cosgrove’s departure is a good thing for the school and its students, letting her retire in this way provides for no accountability for her involvement in all the scandals. To the contrary, it could be read as sending the message that she was a model administrator, as suggested by Gerken’s praise of Cosgrove in the retirement announcement. (But note how restrained, impersonal, and matter-of-fact the Gerken email is; I know, from having seen her do it in the past, that Gerken can offer much warmer encomia when she wants to.)

If you’re just a casual follower of the Yale Law drama, you can stop reading here; I’ve given you the actual news. But if you’re devoted to every delicious twist and turn in this soap opera, keep reading for a closer look into the rise and fall of Dean Ellen Cosgrove. (This account is based on sources who include current and former faculty members, administrators, and students, but to protect their anonymity, I’m going light on direct quotations and on attribution.)

Like many YLS administrators, Cosgrove brought impressive credentials and experience to the job. After graduating from Mount Holyoke in 1984 and from the University of Chicago Law School in 1991, she practiced for four years at LeBoeuf Lamb (later Dewey & LeBoeuf, may it rest in peace). After Biglaw, she began her decades-long career in law school administration, serving as associate dean and dean of students at two top law schools: her alma mater of U. Chicago, for nine years (1995-2004), followed by Harvard, for 11 years (2004-2015).

As suggested by her solid stints at both institutions, Cosgrove was a generally popular and respected administrator at both Chicago and HLS. Her time at Harvard included the entire tenure of Dean Elena Kagan (2003-2009), who brought Cosgrove over to HLS from Chicago, and Cosgrove received some of the credit for Dean Kagan’s successes, including dramatically improved student satisfaction and morale.

I say Cosgrove was “generally popular and respected” because issues did arise at HLS, as they inevitably do. They included a controversy over a sexual-assault investigation that Cosgrove was involved with as Title IX coordinator, a former student alleging mistreatment at Cosgrove’s hands, and an administrator who reported to Cosgrove getting charged with stealing more than $100,000. And there were other kerfuffles—for example, a controversy over authorization for a student-planned outing that was strikingly similar to the controversy over the Yale Federalist Society retreat—but they didn’t make headlines.

On the whole, though, Cosgrove was seen as successful at both Chicago and Harvard. So it wasn’t surprising when then-Dean Robert Post lured her away to Yale in 2015, after a search conducted by a faculty committee led by Professor Kate Stith. When Dean Post was succeeded by Dean Gerken in 2017, she retained Cosgrove as dean of students. (The two overlapped at HLS from 2004 to 2006, when Gerken was a faculty member there, but it’s not clear how much interaction they had.)

The first few years of Cosgrove’s time at Yale, under Dean Post and then Dean Gerken, were uneventful—at least in the public eye. There were some internal controversies involving Cosgrove, including a few personality clashes, but they didn’t make it beyond the walls of YLS—and certainly didn’t make national news.

Things started to go less smoothly for Cosgrove when Professor Michael Wishnie began assuming a larger role in the YLS administration as Counselor to the Dean. As Wishnie’s influence grew—think of him as the Hand of the Queen—Cosgrove felt increasingly sidelined. Her relationships with Wishnie and other colleagues, already not great, deteriorated further.

Some of Cosgrove’s issues stemmed from her difficulty transitioning from Harvard Law, a large school with a large staff and well-oiled administrative machine, to Yale Law, a small school with a small staff that can be a bit shambolic get away with being less well-managed because it’s so small. Cosgrove had to be more hands-on and detail-oriented at YLS, which didn’t play to her strengths. A common complaint was that she didn’t respond promplty to emails about urgent matters—perhaps because at HLS she had a larger staff that handled such matters for her, letting her focus on the big picture. To the annoyance of some YLS colleagues, she regularly complained about how much better-run HLS was and how well-loved she was back in Cambridge.

But these weren’t dealbreakers, and Cosgrove, who’s around 59, probably could have ridden things out at YLS until she turned 65. Instead, she was done in by the three scandals—Dinner Party-gate, Trap House-gate, and the March 10 protest debacle—or four scandals, if you count FedSoc-gate as separate from Trap House-gate.¹

Yale FedSoc isn’t the only student group that has problems with Dean Cosgrove. For example, she’s also unpopular with members of the Yale Black Law Students Association (“BLSA”). Members of FedSoc and BLSA don’t agree on much—they found themselves on opposite sides during Trap House-gate—but they share an aversion to Dean Cosgrove.² Indeed, disapproval of Cosgrove as dean of students is so widespread among the YLS student body that Cosgrove was a top target of this spring’s Yale Law Revue parody show. (Gerken also wasn’t spared; a recurring bit featured “Good Heather” and “Bad Heather” fighting for control over the dean’s soul.)

Considering how unpopular Cosgrove was—as one former colleague told me, “she really doesn’t have a constituency,” at a place where you need at least some faction supporting you—many were surprised at how long she managed to hang on. Trap House-gate happened nine months ago, yet Cosgrove still works at 127 Wall Street (and she’ll be there until her final day on August 12). In the words of one YLS alum who’s now an administrator at another law school, “I don’t understand how Ellen’s still there. She’s like a cat with 20 lives.”

Alas, it appears that those lives have run out. In Game of Thrones, Littlefinger outlasted dozens of other characters—but even he couldn’t outrun fate in the end.

UPDATE (1:38 p.m.): After this story was published, I heard from a Harvard Law alum with warm words for Dean Cosgrove: “Dean Cosgrove was great to Fed Soc students when I was at HLS. I worked with her and had a really positive experience. But, maybe that related to the overall inclusive tone that then-Dean Kagan set.”

UPDATE (2:26 p.m.): More praise for Dean Cosgrove (from a personal rather than professional contact): “I know Ellen through Mt. Holyoke stuff. She’s lovely and low-key. Also worth noting: her husband has been retired for years, so all of this aside, I think she was considering it for awhile.”

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1. Here’s a quick refresher on FedSoc-gate. Last fall, Cosgrove and Eldik met with Zack Austin, then-president of the Yale Federalist Society, and blamed Austin and FedSoc for the Trap House email—even though there was no evidence that they were involved (since they weren’t). As they did with Trent Colbert, Cosgrove and Eldik pressured Austin to send out an apology that they had so kindly drafted for him—which he did not do.

And that wasn’t the end of it. Two weeks later, Cosgrove and student affairs director Chloe Bush attempted to retroactively deauthorize the Yale FedSoc retreat. Cosgrove didn’t back down until Austin presented her with the “Retreat Approval Form” that she had personally signed. In the wake of all this, including Austin’s complaint to Dean Cosgrove that FedSoc could no longer trust Cosgrove and the OSA, Dean Gerken removed FedSoc from Cosgrove’s supervision, designating an administrator outside of the OSA to be FedSoc’s point of contact.

2. The origins of BLSA’s issues with Dean Cosgrove aren’t as clear as the origins of FedSoc’s problems. Some trace it back to an incident a few years ago in which she chastised a 1L member of BLSA over GroupMe messages that Cosgrove viewed as inappropriate.

Interestingly enough, given conservative students’ later problems with Cosgrove, it all began when the BLSA 1L used the GroupMe messaging platform to publicly call out a conservative classmate for interning at a right-wing organization. Cosgrove summoned the 1L to her office and scolded her, bringing her to tears—as the formidable Cosgrove has done to more than one student over the years. After the 1L complained on The Wall aka the YLS listserv about how Cosgrove treated her, Cosgrove was reprimanded by Dean Gerken (plus at least one prominent YLS faculty member) for meddling in student matters, along the lines of, “Ellen, these students are adults—let them work out their own problems.”