A Legacy of Leadership, Loyalty, and Lifelong Impact
Howard Alper, SJMA Class of 1947
“I’ve been playing tennis since I was nine years old. At St. John’s, I was on the tennis team,” recalls Howard “Howie” Alper, a proud graduate of the Class of 1947. His love for the sport has spanned a lifetime, but it was at St. John’s Military Academy that Howie truly found his footing, both on and off the court.
As a teenager in Chicago, Howie admits he wasn’t the most focused student. “When I was 16, I wasn’t exactly dedicated to school. My buddies and I would skip class at Senn High School, head to the pool hall, catch a ball game… never anything bad, just a little mischief,” he says with a chuckle. But after two rough academic years, his parents decided it was time for a change.
That change came in the form of St. John’s Military Academy. Though initially reluctant, Howie remembers the suspense of waiting to hear if he was accepted. “Senn High School had already started classes, and I still hadn’t heard back from St. John’s. I was secretly hoping to stay put,” he admits. But the letter came, he was in — and it would alter the course of his life.
A Turning Point
St. John’s brought structure and discipline, two things Howie credits with giving him the confidence to apply himself in a real way and achieve great things. “The Academy shaped me,” he says. “It taught me how to focus, how to strive, how to succeed.”
One of Howie’s most vivid memories is being awarded the Math Medal, given to the best math cadet — a moment that marked a personal turning point. He also collaborated with General Farrand’s daughter, Dorothy “Dotti” Farrand, to write the Class Poem, which beautifully captured the bittersweet emotions of graduation. An excerpt reads:
“The day has come, my classmates, that we have dreaded so,
And mingled with our happiness, our tears unbidden flow,
For we are leaving old St. John’s, leaving friendships true,
And it’s so hard to say farewell to all the things we knew.”
Pride and Purpose
For decades, Howie remained connected to the values instilled at St. John’s. He later became a successful businessman and entrepreneur and used that platform to positively influence others. One friend shared, Howie was our family’s friend, but he was much more than that. When my parents told him I was having trouble in school, he took us all to visit St. John’s that same weekend. He knew what the school could do for someone like me because it had done the same for him.
Howie founded Alper Services LLC, a respected insurance and risk management firm. Though he eventually sold the business, he considers building it to be one of his proudest professional achievements.
He has also found lasting happiness in his personal life — married to his beloved wife Deena for 43 years, with whom he shares a deep bond and a life of meaning.
Giving Back
Howie is now establishing a scholarship program to support enrollment and ensure the vitality of St. John’s Northwestern Academies. “When I attended, there were over 400 cadets. Now, it’s about 240,” he notes. “My goal is to strengthen St. John’s by helping bring in new students because they’re the lifeblood of any school.”
His pride in St. John’s is unmistakable. “I feel much closer to SJN than the University of Illinois,” he reflects. “Because it was a far more important and meaningful part of my life.”
Howie Alper’s story is one of transformation, mentorship, and enduring generosity. His legacy lives on not only in the halls of St. John’s but in every student who finds their way, just as he did, through the gates of the Academy.
About SJNA:
St. John’s Northwestern provides a safe, structured environment where students build a strong foundation for success. With specialized programs tailored to future aspirations, SJNA prepares young leaders to excel academically, professionally, and personally. Learn more at sjnacademies.org.