Five University of Chicago Law School alumni will clerk at the US Supreme Court during October Term 2026, serving four different justices.

The alumni will clerk for Justices Elena Kagan, Neil Gorsuch, Brett Kavanaugh, and Ketanji Brown Jackson. Two of the five will serve in Justice Gorsuch’s chambers.

UChicago Law graduates have served as Supreme Court clerks in all but one of the past 54 Terms, working for justices across the ideological spectrum appointed by presidents of both parties. The number varies from year to year: during the current Term, seven alumni are clerking for seven different justices, while October Term 2021 marked a recent high point, with nine alumni serving nine members of the Court.

The Law School’s placement at the Supreme Court level reflects its broader record in federal clerkships. For four of the past five years, including this year, UChicago Law has ranked first nationally in the percentage of graduates securing federal clerkships.

“Our students are trained to engage closely with legal doctrine and to write with clarity and precision,” said John Rappaport, one of the co-chairs of the Law School’s Clerkship Committee. “Those skills are central to the work of a Supreme Court clerk.”

Professor Jonathan Masur, the other co-chair of the Clerkship Committee, added, “We are especially proud that these five alumni will clerk for four different justices—Justices Kagan, Gorsuch, Kavanaugh, and Jackson. Their success reflects the Law School’s culture of rigorous engagement with the law and demonstrates that UChicago is a place where students of many backgrounds and viewpoints can thrive and achieve at the highest levels.”

The following five alumni will clerk at the US Supreme Court starting this October.

Tyler Lindley, ’21, and Matthew Rittman, ’23 (Justice Neil Gorsuch)

Tyler Lindley, an associate professor of law at Brigham Young University Law School, is one of the two alumni who will clerk for Justice Neil Gorsuch. At UChicago Law, Lindley was a Kirkland & Ellis Scholar and served as business & communications editor for the University of Chicago Law Review. He graduated with highest honors and was designated a member of the Order of the Coif. During law school, Lindley served as a judicial extern for Judge Ryan Nelson of the US Court of Appeals for the Ninth Circuit. He later clerked for Chief Judge William Pryor of the US Court of Appeals for the Eleventh Circuit and for Judge Gregory Katsas of the US Court of Appeals for the DC Circuit. Between clerkships, he served as a research fellow at BYU Law.

Lindley said he was inspired to pursue a Supreme Court clerkship after hearing about the experiences of UChicago Law professors who had clerked at the Court. “It confirmed what was already apparent from the outside—the Supreme Court is the highest level of reason and deliberation; exposure to that process is both an honor and an opportunity that cannot readily be duplicated elsewhere.”

Reflecting on his education, he said, “From the first seminar in orientation through upper-level courses and clinics, the Law School challenged me in ways that helped me critically analyze my own positions and steelman the other side’s argument. Repeating this process often points you toward truth, the ultimate goal of an education.”

Looking ahead, Lindley expressed excitement about working at an institution “trying to find the right answer in hard cases” alongside the justices and other clerks, including his fellow UChicago alum, Matthew Rittman, who will join him in Justice Gorsuch’s chambers.

An associate at Cooper & Kirk in Washington, DC, Rittman graduated from the Law School with high honors and was designated a member of the Order of the Coif. He previously clerked for Judge Andrew Oldham of the US Court of Appeals for the Fifth Circuit and Judge Gregory Katsas of the US Court of Appeals for the DC Circuit.

What drew Rittman to the Supreme Court was its storied history and the opportunity to contribute to the institution, he said. “I also like hard legal questions, especially questions that relate to the proper role of courts and other actors in our constitutional system. The Supreme Court deals with more of those questions than any other institution.”

He credited his prior clerkships as essential preparation. “Both of my judges are great people and great lawyers, and I certainly wouldn’t be clerking at the Supreme Court without their help. I’m very grateful to the people in the Law School who helped me secure those clerkships. That was essential.”

Asked about the presence of multiple UChicago alumni in the incoming class, he said, “It’s great to have classmates doing lots of interesting things, including clerking at the Supreme Court. It’s a testament to the intellectual climate. And I’m especially excited that one of my co-clerks will be a fellow alumnus. Tyler Lindley is very smart, and I know I’ll learn a lot from him.”

Nena Benavides, ’22 (Justice Ketanji Brown Jackson)

Nena Benavides, currently an associate at Munger, Tolles & Olson in California, will clerk for Justice Ketanji Brown Jackson. At the Law School, she was the comments editor for the University of Chicago Legal Forum and a Rubenstein Scholar. She graduated with highest honors and was designated a member of the Order of the Coif. She clerked for Judge Michelle T. Friedland of the US Court of Appeals for the Ninth Circuit, and for Judge Gary Feinerman and Judge Matthew F. Kennelly of the US District Court for the Northern District of Illinois. She practiced at Bartlit Beck in Chicago before joining Munger, Tolles & Olson.

Reflecting on her time at the Law School, Benavides said, “My extraordinary professors at UChicago taught me how to approach a complicated case, grapple with its nuances, and understand its relationship to recurring themes in the law. UChicago trains its students to zoom in on the holdings of a particular case and zoom out to see the practical implications of caselaw, which has served me immensely in my clerkships thus far.”

She added, “UChicago is a place where everyone truly enjoys learning collaboratively and thinking critically about the law. That passion for the law that I fostered at UChicago motivates me to dive into each new challenge.”

Benavides said she is thrilled to serve alongside fellow alumni. “I was always in awe of the brilliance of my classmates, so it is heartwarming to share this dream come true with them.”

Annie Kors, ’23 (Justice Elena Kagan)

Annie Kors, currently a fellow at Gupta Wessler in Washington, DC, will clerk for Justice Elena Kagan during October Term 2026. She previously clerked for Chief Judge Sri Srinivasan of the US Court of Appeals for the DC Circuit and Judge Vince Chhabria of the US District Court for the Northern District of California. At the Law School, Kors served as editor-in-chief of The University of Chicago Law Review. She graduated with highest honors and was designated a member of the Order of the Coif.

“I loved my time at UChicago Law,” Kors said. “I got to learn from incredible professors who taught us not only about the substance of various legal doctrines but also about how to thoughtfully and rigorously analyze legal problems. And I was surrounded by brilliant classmates who I learned from every day—in the classroom, during my time on journal, and just talking in the Green Lounge.”

Kors also said that the work she did at the Law School helped set her up for success on her clerkship path. “A lot of my time in law school was dedicated to journal: discussing and debating articles, editing pieces from the structure down to the sentence level, helping staff members develop their ideas into comments, and working on my own comment with faculty and other editors,” she explained. “I feel that the skills I learned from those interactions have already been meaningful in the first few years of my legal career.” 

Madeline Prebil, ’21 (Justice Brett Kavanaugh)

Madeline Prebil, currently an associate in the Washington, DC, office of Williams & Connolly, will clerk for Justice Brett Kavanaugh. At the Law School, she was the comments editor for the University of Chicago Legal Forum and was the recipient of the Sidley Austin Prize and the Mark Mamolen Prize before graduating with high honors. She went on to clerk for Judge Toby Heytens of the US Court of Appeals for the Fourth Circuit and Judge Stephanie A. Gallagher of the US District Court for the District of Maryland.

Prebil said her earlier clerkship experiences inspired her to pursue the Supreme Court clerkship. “Judge Gallagher taught me how to tackle issues efficiently, while Judge Heytens prompted me to consider them more deeply,” she said. “Both convinced me that my contributions to chambers were valuable. Without them, I would not have had the skills or confidence to apply.”

Reflecting on her time at the Law School, Prebil said, “The UChicago community taught me to disagree joyfully. I loved the professors—and classmates—who respectfully challenged my settled views.”

Prebil said she is eager to begin. “I feel like I have courtside seats at the All-Star game. I might be most excited to prepare for and attend oral arguments, but I am generally pumped to see the Greats at work.”

Advice for Future Clerks

The alumni emphasized preparation, intellectual curiosity, and sustained engagement with legal scholarship as key to pursuing judicial clerkships.

Lindley advised students to focus first on developing as lawyers rather than narrowly targeting a particular outcome. “UChicago Law provides such an incredible education—take advantage of it to the fullest,” he said. “If you are in the right position to be hired as a Supreme Court clerk, you will be prepared.”

Rittman emphasized academic preparation and close attention to the Court’s work. Strong grades and prior clerkship performance, he said, are essential foundations. “Keep up with the Supreme Court’s docket and try to engage with important scholarship,” he added.

Benavides encouraged students to explore the Law School’s academic and experiential offerings. “Take advantage of the amazing opportunities at UChicago, such as the clinical programs and journals, and stay open-minded as to where your legal interests may lead you,” she said. “There is not one right path.”

Kors counseled students to “take things one step at a time, and to pursue opportunities that excite them and involve the legal questions and types of work that interest them.”

Prebil encouraged perspective and intellectual humility. “Read and write as much as possible,” she said. “Surround yourself with people you admire—and remember there is always more to learn.”

Building on a Tradition

The five appointments continue a decades-long pattern of UChicago Law alumni serving in chambers across the Court, a record that spans multiple chief justices and shifting Court priorities. As the justices convene for October Term 2026, UChicago Law graduates will again be among the small group of clerks assisting the Court in cases that shape national law.