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Harry Rossi (EdD ’85) earns national education award for decades of shaping the lives of students

By Amanda Friedlander (’18)

Unraveling his maroon-and-gold Loyola Ramblers scarf, Harry Rossi (EdD ’85) makes himself comfortable at one of the Schreiber Center lobby tables and whips out his newest-generation smartphone. The way he sauntered into the building—hair slicked back, leather jacket unbuttoned, silver Aviators reflecting the bright overhead lights—Rossi immediately commands attention. But just a few minutes with him reveals this first impression to be deceiving. 

Rossi waited patiently while I fumbled with my pen and notepad, making small talk about the unseasonably warm Chicago winter. Though I was there to interview him, he seemed genuinely interested in getting to know me as well, revealing a humility that would surface throughout our conversation. But all it took was one question about what inspired him to pursue a career in education and Rossi took the reins, not stopping until he’d inadvertently checked off every question I had prepared for the interview.

When asked to talk about his life’s work, Rossi is quick to deflect the conversation away from himself.  After a few minutes briefly outlining his own education and career path, Rossi—who in March will fly to New Orleans to receive the 2017 American Association of School Administrators Distinguished Service Award—spent the next 20 describing the unending love he has for his students and for the teachers who shaped his own path. 

His own high school teachers, he says, were his inspiration for a career in education and school administration. “Teachers saved my life,” he says.

One wouldn’t expect someone so accomplished to have had a childhood that needed saving, but Rossi had humble beginnings. He grew up in a rough neighborhood on Chicago’s West Side, where many of his peers didn’t do well in school or go on to college. Rossi himself excelled in academics and sports, but it was the encouragement of his teachers that determined his life’s path. He remembers them telling him he could do anything he wanted to do, and for Rossi, that meant making a difference in the lives of other young people.

Rossi has done just about anything he’s wanted to do; he’s held jobs all across the educational spectrum, from teacher to CEO of FED-ED, a lobbying group that advocates for more than 110 school districts and 500,000 students. Rossi has also taught Loyola students for more than 20 years as an adjunct professor in the School of Education, teaching one or two courses every semester for graduate students with similar dreams of administration and student advocacy.

Rossi’s passion for Jesuit education, and for helping students from low-income communities, has also made him a staunch supporter of the Cristo Rey Network of high schools. “It’s a wonderful model of giving kids from inner city schools the opportunity to get a really good Jesuit education, work experience, and get them ready for college,” he says. 

Many of Rossi’s former students are now administrators for Cristo Rey, including the president of the network. And along with his wife Diane (EdD ’05), Rossi helps to provide financial aid for Cristo Rey graduates to attend Loyola through the Harry and Diane Rossi Scholarship Fund. 

Rossi’s ongoing commitment to Loyola doesn’t end there. He’s been a longtime member of the National Alumni Advisory Board and a member of the Rambler Varsity Club advisory board. And you can often find him in the crowd at men’s basketball games, which he’s been attending as a season ticket holder for the past 40 years.

These days, Rossi is starting to step back from his leadership positions to spend more time with his family, all of whom are lifelong Ramblers. His wife Diane is both a fellow alumna and a faculty member in the School of Education. The couple’s children, Phillip (BBA ’00) and Elizabeth (BA ’01), both attended Loyola on presidential scholarships. Even his eight-month-old grandchildren share in the Loyola legacy. Rossi beams with pride when he describes their infant-sized Rambler scarves and baby booties.

Earning the Distinguished Service Award, a national honor given to administrators who have made a major impact in the field of education through service and advocacy, is something Rossi takes in stride. It isn’t the first time he’s been honored for his work, or more accurately, the first time someone has attempted to honor him. He’s been nominated for many different awards but declined each time, not wanting to devote district resources to himself. What makes this award special, he says, is the fact that a student took the time and put in the effort to nominate him.

But don’t expect him to collect the award and disappear. Though he’s slowed down in recent years, Rossi isn’t likely to leave the classroom behind anytime soon. He’s insistent that as long as he’s in good health, school administration and student advocacy will always be a part of his life. 

“I’m not a person who just wants to sit in a rocking chair and move to Florida,” he says. “I don’t see myself as that person doing nothing. Teaching here keeps me young.”


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