Tom Owen: “It Seemed Like A Good Idea At The Time”

As a Staples High School student in the early 1970s, Tom Owen had great teachers. But, he admits, “I wasn’t as invested in them as they were in me.”

A self-described “jock” who claims football, skiing and baseball got him through school, it’s not surprising that Owen ended up coaching at his alma mater.

It’s harder to believe he also spent the past 36 years as a teacher there.

Owen retires this month after a storied career. He coached Wrecker golfers to 3 state championships — he was an all-around jock — and “15 or 20” boys and girls state skiing titles (he lost track during his 23- and 5-year Staples stints, with 8 years at his son and daughter’s Joel Barlow High School in between).

But his impact is even greater on countless special education students. He guided group after group from 9th grade to graduation — and remained their mentor far beyond.

Tom Owen, Staples High School Class of 1974.

Tom Owen, Staples High School Class of 1974.

It was an unlikely career for a kid who spent his freshman year at Norwich University — a private military school in Vermont.

“That didn’t go so well,” Owen laughs. “I thought I could ski every weekend, and carry on my high school shenanigans. Instead, I ended up walking thousands of tour duties.”

Transferring to Ohio University was a better choice. He joined the rugby team — a jock is a jock — and after sophomore year, told a counselor he wanted to be a phys. ed. teacher.

She suggested he look into a new field: special education. It appealed to him — particularly because he could coach after school.

Owen started as a Staples paraprofessional in 1979. That same year, Long Lots Junior High football coach Bob Yovan retired. His former school — the same place he’d met his future wife, Deb — handed the 24-year-old his 1st head coaching job.

He quickly realized how lucky he was. His 2 jobs — teaching and coaching — brought him in contact with tens of thousands of “amazing” people. “I couldn’t believe I was getting paid to do this,” Owen says. “I had the greatest interactions with kids, parents and colleagues. I got to be a teacher for students, a counselor for families, an educator and a mentor.”

Tom Owen liked taking students out of the classroom. He believes learning can take place in many ways, and many places.

Tom Owen liked taking students out of the classroom. He believes learning can take place in many ways, and many places.

In the 1990s, he and longtime fellow teacher/friend/sidekick Diann Drenosky — who also retires this month — worked in a separate building near Staples’ 9 Building. “The Little House” provided an innovative way to teach both academic and living skills. The kids were tough, but Owen, Drenosky, paraprofessional Ann Rully and Westport Police youth officer Arnie de Carolis created a warm, family atmosphere there.

“It was a great program,” Owen says. “We were devastated when it ended.”

Generations of students are grateful that he and Drenosky remained a team. “We laughed a lot — at each other, and ourselves,” Owen recalls. “We cried some too. She’s a special person, and she touched so many people over the years.”

Coaching allowed Owen to reach other students, in different ways. “Looking back, I can’t believe the amount of time and emotional investment I put into it,” he says. Football and golf are demanding enough; he just shakes his head at the memory of “standing on the Southington ski slope at 9 p.m., when it’s minus-30 degrees.”

Much has changed over the past 36 years, of course. As a coach, he’s seen far greater parental involvement — for better and worse.

Tom Owen met Debbie Goustin -- his future wife -- at Long Lots Junior High School.

Tom Owen met Debbie Goustin — his future wife — at Long Lots Junior High School.

“Parents help a lot with organizing now,” he says, declining to discuss the negative aspects. “My parents basically just showed up at a few games.”

He has the special perspective of having attended the same school where he spent his entire teaching career.

“Things were so casual back then,” he says of his student days. “The stress level was way lower — maybe to a fault. The stress kids have today is over the top.

“We were much more independent. Our parents were way less involved. We solved things more on our own.”

He is not putting today’s teenagers down, he notes. “That’s just the way it is. I would have done better in school if I was under all the rules and regulations we have today. I definitely took advantage of the lack of discipline.”

But, he adds, “I wouldn’t do anything any differently.”

Owen’s free-spirited attitude continued into adulthood. At his retirement dinner, colleague Tony Coccoli said, “Every Tom Owen story ends with, ‘It seemed like a good idea at the time.'”

Coach Tom Owen, on the golf course.

Coach Tom Owen, on the golf course.

Retirement will give the self-described “jock” more time for sports. He and Deb’s children, Patrick and Lex, spend winters at Jackson Hole. Owen may become a ski instructor, and/or work in a golf pro shop.

“I’m 59 years old,” he says. “I’ve ‘gone to school’ for 54 of those years. This fall will be a big adjustment.

“I look forward to it. But I feel really, really fortunate to be part of Westport for so long.

“While you’re in the middle of it, things just happen. But now as I get away from it, I realize how in many ways, this town and school defined who I am.”


32 responses to “Tom Owen: “It Seemed Like A Good Idea At The Time”

  1. Congratulations T.O.!!!
    Thanks for ALL you have done for our school and our kids!!
    Here’s to you and your family and your well earned retirement!!

    Tom Wall

  2. Congrats Tom,Thank God you survived when my dad caught you crawling into my sister’s room and threw you down the stairs 🙂

  3. Sounds like a super successful life! – Chris Woods

  4. Scott surprise

    Excellent job Tom Owen

  5. Michelle Borgia Howard

    Tommy, Congratulations on an amazing run! You will be missed. The Borgia girls loved being part of Staples Ski Team with you at the helm. I know all the Steve Miller Band lyrics from countless rides to and from Southington and everytime one of those songs hits the raido, it brings back terrific memories. Best to you, Deb and the kids! Be well and enjoy the next chapter. I’d go for ski instructor over golf pro 🙂
    Michelle Borgia Howard

  6. Jennifer Rankine

    Thank you Tom, for your tremendous contribution to Staples and the students. You will be missed. Enjoy your retirement!

  7. Frank E Accardi

    A great teacher ,coach and a generous ,compassionate ,friend to all who needed him.
    All the best ,
    The Accardi Family

  8. Betty Lou Cummings

    Dear Tom & Debby too….you both have given so much to our kids….Tom coached Matthew & Todd both on the Staples Ski Team (Captains). We enjoyed the years of knowing Tom….Debby at Ludlow’s (VT) Craft Fair will be missed too….many hugs and thanks for so much….Betty Lou Cummings and Family

  9. Tom Siebrasse

    Congrats Tom, Great run! I still remember us in CP typing, one of the most useful courses we ever took at Staples no doubt. Now Deb gets to put up with you full time, lucky girl…

  10. Megan Acquino Slingo

    Best coach ever!!! Thanks Tom for giving me the opportunity to join the boys Golf team back in the day….there was no girls team back then…even though I only stayed 2 years…it was a blast…and I certainly learned from your example of how to be a great coach!!!

  11. Greg Zeglen

    ….this showed up in my inbox this morning – it was forwarded by my daughter who lives in Westport…I was the beer man that made certain that the OU Rugby team had sponsorship money in the 70’s…pleasant memories of great times.

  12. David Eason

    Good for you Tommy!! I can remember some interesting bus rides back in the day. Enjoy your retirement, well deserved.

  13. Philip Ross

    Tom was an incredible ski team coach.
    His state championships and winning percentage are unmatched in the state history. He coached teams to 13 state championships with a record of 273-52. He was well likes by his fellow coaches and his racers.
    Good luck Tom

  14. Tommy, you truly are a”one off!” — a rather remarkable combination of compassion, patience, professionalism, competitiveness, energy, and wit — lots of WIT! Whatever you decide to do come September, as usual, you are going to knock it out of the park. Val and I are fortunate to be able to count you and Debbie as friends!

  15. David Squires

    Good Story Dan, TO is one of a kind…
    No doubt they Broke the Mold!

  16. I was fortunate to have TO every year at Staples. Makes me sad that there are generations of kids who won’t have the guidance he gave me. 10 years later I still call him time to time to check in. One of the few teachers that really made an impact on my life. Thank you Tom. I am confident you will still never age in retirement.

  17. When I started my career in teaching 21 years ago by subbing Tom was as helpful and gracious as could be in ‘showing me the ropes’ at Staples. I worked with Deb in New Canaan and she was as dedicated as could be to the kids and the craft. Power Education Couple!

  18. Janet Wolbrom

    You’re an inspiration, kind hearted, and so much fun to be with Tommy. You have a wonderful ability to make instructions understandable. Thinking of you always brings on a smile. Congrats! Enjoy your retirement.

  19. Matt Storch

    Well deserved TO. I’m sure I will run into you on a course or a chairlift soon. I could not have asked for a better coach, mentor and friend during my high school years. I was lucky enough to enjoy your company for 4 years on the course and on the slopes, you have no idea how much I want to go back to those times!! Way to much fun without a care in the world. I know you will enjoy every second of your retirement! Thank you!

  20. Kurt Brockwell

    Tom thanks for coaching me at Long Lots & Staples. A lot found memories setting up down records during football seasons. Enjoy retirement you earned it! Brock

  21. Congrats, Tom. I can’t believe we are now so old you are retiring. Maybe retiring isn’t the right word if you’re going to be a ski instructor or work in golf. I haven’t seen you in years, but I hope we can catch up sometime before too long. Just looking at your photos gives me a great laugh, because I can’t ever remember a time in your presence when you weren’t making people laugh, and I mean laugh hard. Once a comic and entertainer, always a comic and entertainer. Few people on the planet have ever had a sense of humor as good as yours.

    So here’s a toast to you, ol’ buddy. Good times playing softball with you on the Trojans, and lifeguarding with you at Compo Beach. “Killer workouts” as lifeguards keeping in shape in the guard shack, and, oh, man, those unbeatable lifeguard parties.

    Again, congrats! I hope to catch up again before too long.

    Cheers, buddy!

  22. Christian V. Bergmann

    Thank you, Tom…magical times – Staples Ski Team 1979 – 1982. Tom Owen is music…and music is best.

  23. Jay ODonnell

    Tommy, On behalf of my brother, sister and myself I want to thank you for keeping us off the streets all those years on Ski Team – what a blast! Besides being a great coach I’d be remiss to not also recognizing your couples counseling (refereeing) skills on the bus rides home :-). You’re a legend my friend, you will be missed. Enjoy retirement you lucky bastard!

  24. John Siddell

    Congratulations Tom…thanks for keeping me in line of the golf course 😉 Best of luck to you & Debbie…well deserved!!!

  25. Ilene Kaplan

    wow Tom, it’s been a lifetime!! We had lots of good times together..and tho I am a grandma, I can’t believe you are retiring! Love to you and Deb and the kids from Donald and I.. Congratulations, Ilene Kaplan

  26. Matthew Evans

    Tom, thanks for everything you did to make the Staples Ski Team a reality. Ski team was a huge part of my high school experience.

    Congrats and best of luck in your next phase. I know you will continue to inspire people and make a difference in whatever you decide to do.

  27. Frank Henrick

    Tom, you are one of the best teachers I had the pleasure to work with. You did so much for those who needed your thoughtful, loving, good natured leadership. Thanks for being in my family’s lives.
    Best of life’s blessings in your new “career.”

  28. Neil Passero

    Tom Owen is a great man with a great smile and a huge heart. All the best to you in retirement, T.O!

  29. As a parent (son Brendan with Staples golf team), opposing coach (Fairfield
    Prep golf team), and collaborator (Chappa Tournament), I appreciate Tom’s approach to coaching and his rapport with parents. My family and I wish him a wild and satisfying retirement doing whatever he wants to do, in his own time and schedule.

    Roger Ratchford, Ed.D.

  30. Hey Tommy, congratulations on a great career! You always made practice fun and had a great connection with the players. You also had an amazing knack for coming with some of the most hilarious nicknames. You’re a great coach and even better person. Enjoy your retirement!!!

  31. Vanessa Bradford

    Hey Tom, Congrats on your retirement and welcome to the club! Trust me you won’t be bored! All the best and cheers to a Staples High School legend! Vanessa Bradford