Ann Cherry has been collecting memories from Homewood-Flossmoor High School graduates the past 13 years.
“I’m in the business of nostalgia,” the H-F director of development and alumni relations said. Her work is a lot of “good feelings and reawakening those good feelings with people. It wasn’t hard to do here at H-F.”
Cherry said the school, founded in 1959, has 40,000 alumni in every state and more than two dozen countries, noting: “I can’t think of a profession that isn’t represented.”

She shares a story of two U.S. State Department employees in Kazakhstan who met at a reception. They learned they had both graduated from H-F, one year apart. There are dozens of stories like that.
Cherry is stepping down from her position June 30 after first helping to establish the office and then working to grow the connections with graduates.
Her first task was to develop a database of alumni. She borrowed from the H-F Foundation’s alumni directories, input what information she could glean and added every class at graduation and every bit of information she received or learned at class reunions and school events.
“I built relationships and name recognition. It’s rare that only one person comes through H-F. There’s usually siblings,” she said. Cherry said she learned school history from alumni who “would talk about how their parents went door to door with petitions to get this school built.”
It’s not uncommon for alumni to tell her how prepared they were for college and careers because of H-F. As teenagers, they didn’t realize how special H-F was, and they marvel at the changes to the school. In the 13 years Cherry’s been on staff, the VTV studios have been updated, the fieldhouse that rivals some college facilities was built, a new Performing Arts Center opened in 2021 and now a new science wing is planned.
“You can’t come here and not be floored by the effort the school and the community always make. People move out here because of the school, from the days it opened the doors,” she said.
There are already a dozen alumni programs on the book for next school year. Cherry said alumni “are proud to come from this H-F community, and that comes into play with their nostalgia, and they’re excited to go to Aurelio’s – always!”
The wonderful experiences students had at H-F made it easy for Cherry to connect with them.
“When I reach out to them, they’ve been very generous with their time. A lot of them drop in on classrooms and COVID made it comfortable for them to do that (via Zoom). So, in some ways we were able to expand our reach to alumni.” She recalled 1969 alumnus Marshall Bautz talking to the H-F astronomy class last year about his experiences as an astrophysicist and associate director at MIT’s Kavli Institute for Astrophysics and Space Research.
Alumni also have longstanding relationships with teachers. When possible, Cherry has included the faculty at alumni events.
She also encourages graduates to reach out to alumni for networking and career opportunities by emphasizing the H-F connections “because it works. We often hear about people who got jobs and internships because of the H-F connection.”
Cherry credits retired Superintendent Von Mansfield for having the vision to create an alumni office at the high school level. Over the years, she’s heard from high schools across the country who want to learn how to emulate what H-F has developed.
“It’s good stuff here in the alumni world and we’re excited when people come back and I feel like our young alumni and recent grads are going to be fabulous. I’m very positive about their involvement in the years to come,” she said.