If someone had asked Jeffrey Brenzel as a Yale undergraduate in 1975 what the chances were that he would end up as Yale’s dean of admissions in 2013, Brenzel would have laughed and “assigned it the same probability as winning the least likely lottery in the country.”

If asked the chances of ending up as both the admissions dean and master of a residential college at the same time, Brenzel would have “not even assigned it a probability.”

And yet — nearly 40 years after his time as a student at Yale — here he is.

Brenzel, Yale’s dean of admissions for the last eight years, will officially step down from his role at the end of the current academic year. Though he will continue serving as master of Timothy Dwight College, Brenzel will leave the admissions dean position to current Deputy Dean Jeremiah Quinlan and return to a teaching role in the Directed Studies Program in Yale College.

“We’ve been incredibly spoiled by Jeff Brenzel, who is, to my mind, a simply extraordinary admissions dean,” said University President Richard Levin in a February interview with the News.

Quinlan said Brenzel has bred an “incredible culture of initiative and responsibility” in the Admissions Office, encouraging staff members to think critically about the admissions process. Margit Dahl ’75, director of admissions, said she has seen people in the office “really thrive” under Brenzel’s leadership, adding that many staff members have stayed on longer than they might have expected for the opportunity to grow and learn from Brenzel’s direction.

Dahl added that Brenzel’s tendency to dig deeply into moral and ethical issues has led the admissions staff to refer to Brenzel fondly as their “in-house philosopher.”

Arriving as a student at Yale from Louisville, Ky., in 1971, Brenzel came from a modest home and immediately found a place in the school’s community, participating in residential college life and performing with the Whiffenpoofs. After pursuing graduate study in philosophy, Brenzel worked in the nonprofit and business world outside of the University before returning to direct the Association of Yale Alumni in 1997.

When Levin first asked Brenzel to take charge of the Admissions Office in 2005, Brenzel said he was extremely hesitant. He had no prior admissions experience, and his job at the AYA had never involved the moral implications of admissions work. But Levin — looking specifically for the type of philosophical understanding that Brenzel could bring to the office — persuaded him to take the role, emphasizing that the admissions process truly stood at “the heart and soul of Yale College.”

“Was it an unusual choice? Yes,” said Mark Dollhopf ’77, the current AYA director and a friend of Brenzel’s during their undergraduate years. “Was it a brilliant choice? Yes.”

San Francisco University High School college counselor Jon Reider — a former Stanford admissions officer and longtime colleague of Brenzel — called him “an unusual guy” among other admissions deans from the start. Whereas admissions deans typically take an internal approach to decision-making, Reider said, Brenzel cast a wide net for the opinions of college counselors and other individuals on the high school side of admissions, thoughtfully weighing their input.

Jonathan Edwards College Master Penelope Laurans, who has worked with the Admissions Office in various capacities since the 1970s, said Brenzel has made significant contributions to the national admissions landscape, helping to play down the importance of numerical rankings — a choice that has caused controversy in college admissions — and partnering with organizations such as QuestBridge to boost college access to low-income students.

The zero-sum nature of the admissions process leads to “incredible frustration” and is “guaranteed to make you agonize,” Brenzel said, stressing the trade-offs and compromises that every dean has to make.

For three of the last eight years, Brenzel has also served as TD master — a dual role that has been “extremely challenging,” he said, sometimes resulting in “collisions in which [he] simply survived, rather than thrived.” But he added that both jobs have been rewarding, especially when they offer him the chance both to select and to guide students in each year’s incoming class.

In his wood-paneled study in the TD Master’s House, Brenzel leaned back in an armchair and reminisced about the course of his career — a meandering path that led him through a number of pursuits, from academia to directing alumni relations in the AYA, to the position of admissions dean from which he will depart in roughly a month.

“Things you can never predict play a far larger role in what you end up doing than anything you’ve planned out,” he said. “I think I would share this with Yale grads in general — what you’re going to end up doing is highly unpredictable.”

For the foreseeable future, Brenzel will continue to serve as TD master and teach in Yale College. Anything after that, he said with a smile, has yet to be decided.