MATTHEW J. DeGREEFF ’89 sits outside his Greenough Hall residence with his Chesapeake Bay retriever BIX. DeGreeff will leave Cambridge after 17 years at Harvard, including nine as a first-year proctor.

Matthew J. DeGreeff ’89, the man who holds the distinction of being the longest-serving first-year proctor, announced last week that he is leaving Harvard.

His departure after nine years as a proctor is just another sign that the era of the veteran proctor has ended at the Freshman Dean’s Office (FDO). In recent years, the FDO has seen shorter tenures for both proctors and assistant deans.

DeGreeff said that while the FDO faces “a lot of natural turnover” among proctors—who he said are increasingly graduate students looking to move on in a couple of years—it would be wise to hire some who will stay long enough to provide institutional memory to an FDO in constant flux.

“I think you need a mix of people, [including some] who will stay around for four or five years,” he said. “I’ve worked with four assistant deans in my nine years, and I think I’ve been helpful to them.”

Dean of the College Harry R. Lewis ’68 said new hiring practices naturally lead to fewer veteran proctors.

“Certainly to the extent that we now recruit more proctors who have families, or want to have families, it shouldn’t be surprising that they don’t stay in the Yard forever,” Lewis wrote in an e-mail yesterday.

DeGreeff is, indeed, a family man—in fact, his son Jeremiah was born on first-year move-in day in September 2000.

DeGreeff has been at Harvard for 17 years—nearly half his life—first as a student, then as an admissions officer and proctor. But this June—after nine years of watching more than 300 Harvard first-years enjoy his famous home-baked cookies—Harvard’s most senior first-year proctor will finally bid adieu to his Greenough Hall suite.

DeGreeff, who currently serves as assistant director of financial aid and senior admissions officer, will join the Middlesex School in Concord as the director of college guidance, assistant head of a boys’ dorm and basketball coach—almost two decades after playing on Harvard’s varsity team.

DeGreeff came to Harvard as a first-year in Greenough in 1985. After graduation, he returned as a proctor to Greenough, where he currently lives with his wife Joyce, director of the First-Year Urban Program, son Jeremiah and Chesapeake Bay retriever Bix.

“Matt DeGreeff, and Joyce, and Bix, and more recently Jeremiah, are such a part of the College that it’s hard to imagine the Yard without them,” Dean of Freshmen Elizabeth Studley “Ibby” Nathans wrote in an e-mail.

DeGreeff said that he has enjoyed his time at Harvard but that his growing family and his completion of a master’s degree at the Graduate School of Education last year have led him to consider a change of venue.

“It’s time that I leave my Harvard cocoon and try something new,” DeGreeff said. “I felt the need to try something new so I started looking at jobs at boarding schools and small colleges.”

DeGreeff said leaving Harvard will have its down sides, too.

“I’ve grown up here professionally,” he said. “I will miss all my friends, deans and fellow proctors.”

Staff members at Annenberg Hall, where first-years take their meals, said they will miss seeing DeGreeff and his family at mealtimes.

“He has the cutest kid I’ve ever known,” Annenberg ID checker Domna Antonia. “Everybody loves the kid. He’s our mascot. He even knows my name.”

Jeremiah made a Valentine’s Day card for the dining hall’s staff, and his picture rests behind the Annenberg check-in stand.

The students in DeGreeff’s proctor group say future first-years are missing out on a unique proctoring experience.

“It’s sad that next year’s freshmen won’t get to know him, and have discussions with him while sitting in a big cushy chair and eating home-baked cookies, and wave to Jeremiah in Annenberg at dinner,” said Charlotte E. Gray ’05.

“Matt really knows how to relate to students. If students are having trouble with something, he knows how to guide them in the right direction while letting them feel like they are making the right decisions on their own,” she said.

DeGreeff said proctoring has been one of his most rewarding experiences at Harvard.

“The magic of proctoring is the day-to-day interaction,” he said. “The big events leave memories but when you help people through really tough times that’s when you really make a difference. You establish lots of small relationships with people that carry with you for the rest of your life.”

DeGreeff has taught that ethic to his students—six of whom have themselves become first-year proctors.

But it is not likely that any of them will stay in the Yard as long as he did—and some of them have already come and gone.

“Historically, there have been more people like myself,” DeGreeff said.

Old-timers today, he said, are people like fellow admissions officer Christine A. Kelley, who has been a proctor for seven years.

“Legendary” proctors in the past, he said, served for 30 or 40 years.

“I think Harvard’s just a different place than it was 30 years ago,” he said.

—David C. Newman contributed to the reporting of this story.

—Staff writer Jeslyn A. Miller can be reached at jmiller@fas.harvard.edu.