Over two days in April, Gilman will welcome back to campus more than 400 alumni and their guests to participate in 26 different events as part of Alumni Weekend 2026. This celebration dates back — in various forms — to 1905, when 14 alumni from the Country School for Boys, as Gilman was then called, gathered for a Christmas Banquet and formally organized an Alumni Association to better connect its graduates back to the school.

In the prelude to this year's iteration, Gilman invited four esteemed alumni to share their experiences with current students during an Upper School assembly — connecting the past with the present — highlighting what has changed and celebrating that which has remained constant at Gilman over the years.

Included on the panel were Michael Weinfeld ’91, president/principal at Kittredge Properties, Khalil Uqdah ’06, president for development at Charm City Buyers, Darius Jennings ’11, associate for multifamily properties at CBRE (D.C.), and LJ Shapiro ’16, second grade teacher and varsity golf assistant coach at Giman.

Weinfeld shared insights into what Gilman was like in the 1980s and 1990s, noting the significant differences in the physical plant and the glaring absence of technology and devices. And, having been a Gilman student, parent, and current member of the Board of Trustees, he recognized that it is the people — both the teachers and the students — that really make Gilman special.

Uqdah spoke of several of his favorite traditions, both serious, like coming together daily for assembly, and more light-hearted (think pranks involving pigs in the Common Room!). And he relayed the truly special, full-circle experience of having recently attended Gilman's Second Annual Community Iftar Dinner more than 20 years after he and several classmates had helped to found the Muslim Student Association.

Jennings joked about being terrified by his first encounter with the Gilman Raiders, later learning to love the school spirit these blue-and-gray marauders promote. He also talked about the skills he developed at Gilman that allowed him to thrive during his seven-year career as an NFL wide receiver and kick returner. This included stressing the enormous value of being a multi-sport athlete and more academic habits like taking good notes, citing your sources, and preparing well for every situation.

Shapiro reflected on the teacher-coach model and the individuals who had impacted him profoundly throughout his journey. Citing folks like fresh-soph soccer coach turned biology teacher Frank Fitzgibbon, he explained the draw of coming back to Gilman to work and joining fellow alumni like Nick Schloeder ’85 and Jeff Gouline ’00 as colleagues.

As a parting shot, the group reflected on all of the things that make them happy about the Gilman of today … and there was plenty to share!