'Not a lot of free time, but I love it': Here are five high school coaches for all season, devoted year-round mentors

Much has been said and written about the demise of the three-sport high school athlete due to the specialization of sports.

But no need to lament the loss of the three-season coach.

There are, not surprisingly, a slew of devoted individuals who coach the trifecta of cross-country, indoor track and outdoor track with Hopedale’s Joe Drugan still going strong at the age of 80.

Then you have the diversified likes of Westborough’s Len O’Neil (soccer, swimming, tennis) and Algonquin’s Kristen Morcone (volleyball, skiing, softball).

And how about Jacob Ramos. He coaches junior varsity girls’ volleyball and varsity girls’ basketball at Blackstone Valley and in the spring heads across the street to Nipmuc to coach JV boys’ volleyball.

Here’s a closer look at five coaches who teach, mentor, guide, and inspire young athletes from August until June before taking the summer to recharge.

Brian Billings

Oakmont Regional

Billings’ entry into coaching began at the youth level as his four kids became involved in sports.There’s Dylan, who now teaches at Oakmont, Reid, Kyle, and the youngest, Riley, who’s finishing up her athletic trainer internship at the University of Denver.

“I did the typical coach-my-kids-in-youth-sports,” Billings, 62, said. “(Then) my oldest son’s seventh grade year I sort of got recruited off the Pop Warner field to come and coach the (Oakmont) JV team in football.

“That was really the start of it. I coached my kids, and it just rolled into high school. Now they’re gone, and I’m still there.”

That was just over 21 years ago. In addition to football, Billings has been an assistant for the boys’ basketball and boys’ lacrosse teams for the past “18 or 19” years.

Billings, who was raised in Bar Harbor, Maine, and settled in Westminster after meeting his wife, Heather, while attending Tufts University, owns Oak Tree Woodworking, which crafts high-end custom cabinets in Winchendon.

“I work a lot of weekends to make up for the time I miss during the week coaching,” he said, “but I enjoy it enough so that I’m still willing to do that.”

What he finds most satisfying is watching the students he works with develop as athletes and mature as individuals.

“Seeing how they turn out on the other end,” Billings said. “I’ve talked to (athletic director) Eric (Dawley) about that, and it’s pretty satisfying to see, to see people grow up and become young men and productive.

“You see them out (later in life), and it’s a pretty cool thing. Other than just the competitiveness of it — I still enjoy that — but just seeing how you can mold them and how they turn out is pretty satisfying.”

The only one of his four kids Billings didn’t coach at Oakmont was Riley. Nonetheless, father and daughter spent many a practice together.

“She literally grew up on a high school athletic field,” Billings said. “I had her in the backpack. Out on the football field with a baby in a backpack. and then when she was old enough to walk, she was just there.”

Lee Diamantopoulos

Shrewsbury High

Diamantopoulos was a three-sport athlete — and captain — at Shrewsbury, from which he graduated in 2001.

And it was Diamantopoulos’ high school coaches — Terry Walles in football, Dave Niro in baseball and his dad, Jim, in basketball — that led him to enter the profession as a three-sport coach four years later.

“I couldn’t ask for three better coaches to have, and especially to play for your dad is very special,” Diamantopoulos, 41, said. “I think getting into coaching was just wanting to provide the experience for kids that I had in high school.

“And obviously stay competitive, too. It was just kind of what I loved doing, what I’m used to doing. So if I wasn’t playing, I might as well coach.”

If you look at high school coaching as tiers, Diamantopoulos has the three levels covered.

He coaches the freshman team in football, the boys’ junior varsity in basketball and the varsity in baseball.So, a steady climb age and skill-wise throughout the school year, albeit one in which the approach and objectives remain the same.

“Obviously there is teaching at every level, and the maturity of the kids is different, but in the end, I try to keep things simple,” said Diamantopoulos, who is a guidance counselor at his high school alma mater.

“We’re there together to improve and support one another and be as competitive as possible. Although the ages might change, the values that you preach remain the same.”

One interesting dynamic in play is that Diamantopoulos goes from being someone who provides input during football and basketball to being the final decision maker in baseball.

Whether he’s giving advice or taking it into consideration, it’s all about working together all the time.

“Whatever role I’m in and, with the mix of coaches that we have, I do whatever I can to help the kids, help the team, help the program,” Diamantopoulos said.

“So, if it’s being the head guy or an assistant, I’m there because I love the sport and want to see us do well. It’s really whatever I’m needed or asked to do.”

Karen Marino

Leominster High

Marino is the teacher now, but she once was the coaching student.

Some 20 years ago, the 1980 Leominster High graduate who served in the Air Force and Air National Guard and earned a degree in exercise physiology from the University of Delaware decided to enter the coaching field.

So she volunteered her services to the Blue Devils’ indoor track teams in return for gaining experience.

“I just wanted to learn as much as I could and get into it,” Marino, 62, said. “I put my time in.”

Now she’s the longtime coach of the boys’ and girls’ teams in cross-country, indoor track and outdoor track.

Marino played field hockey, basketball and softball in high school, so no connection there when it comes to the sports she coaches. But she has always enjoyed running and thinks track offers something for everyone with its various running, jumping and throwing events.

“I like track and field because everybody can run, and I like the specialized events in track and field,” said Marino, who is a personal trainer at Global Fitness Center in Leominster.

“So it gave me an opportunity to learn and grow and work with the kids and use my degree, as well, in a different sort of way.”

Leominster doesn’t have a track, which, Marino noted is a “constant challenge.”

And while she coaches many of the same athletes throughout the school year, Marino is always striving to keep things fresh for the kids. To that end, she is constantly striving to stay up to date on training methods and seeking out new motivational means.

“I learn something new every year,” she said. “It’s a different batch of athletes with a whole new set of challenges.”However, no matter the result, the satisfaction that comes from coaching never gets old.

“We don’t always have athletes who are winning state championships or whatever,” Marino said. “We do have them, but I get just as much enjoyment out of kids who are taking what I’ve taught them, learning and improving through the season and being proud of themselves.

“That’s the best part of it for me. Just watching them grow.”

Kelli McSweeney

West Boylston High

McSweeney goes from coaching middle school girls’ soccer to varsity girls’ basketball to junior varsity softball.There isn’t much of a break between the fall, winter and spring seasons, which can lead to an adjustment period from, say, the court to the diamond.

“The kids joke because at the start of a new season I’ll kind of use phrasing from a different one,” McSweeney, 35, said. “Like at the start of softball, I’ll be like, ‘OK, we’re going to do this passing drill now.’

“And they’re like, ‘Throwing?’ And I’m like, ‘Oh yeah, throwing.’ Or I’ll say ref instead of umpire and things like that.”

Other than those humorous moments, the transition from student-athlete to teacher-coach has been smoother than the Wachusett Reservoir on an August morning at her alma mater.

McSweeney, whose maiden name is Milewski, played soccer and basketball at West Boylston before graduating as valedictorian in 2007. Four years later, she was hired as a sixth grade special education teacher, which led to her accept the administration’s offer to coach soccer.

She’s following in the footsteps of her dad, John Milewski, a former West Boylston baseball coach whose daughter used to do the scorebook for him.

“Our family has been around sports for as long as I remember,” McSweeney said.

Playing different sports provides benefits for athletes in terms of crossover. That’s something McSweeney has been sure to stress as a coach.

“I make analogies for those kids where, ‘This is similar to what you do in this (other) sport,’ ” McSweeney said. “Defense in soccer is very similar to defense in basketball.

“I always joke that, ‘What’s the magic shape in sports? And it’s the triangle.’ That’s the same in softball, going for a fly ball or popup, and you want to have that shape in basketball, too.”

McSweeney exudes positivity and aspires to instill a love of sports in her players, many of whom, what with West Boylston being a school with 450 students in grades 6-12, participate in multiple sports.

She takes great satisfaction in aiding and observing their development in the classroom and, for example, on the court.

“A lot of the kids I had for basketball this year, I knew them as sixth graders,” McSweeney said, “so that has been a great perk to our small school and small community. Just to see them grow up from sixth graders to seniors and be part of their athletic journey.”

Dave Wooten

Grafton High

One thing led to another and Wooten, who only played hockey at Grafton, found himself coaching sports from the start to the finish of the school year at his alma mater.

And he couldn’t be happier.

“What else am I going to do?” Wooten, 37, said. “Not a lot of free time, but I love it.”

In 2010, five years after graduating from Grafton, Wooten was brought aboard to coach the junior varsity baseball team, replacing his close friend, L.J. Tosches, who was headed off to law school. He has been with the program since and was elevated to varsity pitching coach last spring.

Then, after volunteering his services to the junior varsity hockey team in 2012, Wooten eventually was hired as the JV coach and made his way up to the varsity, helping Grafton win the Division 3A state title in 2017.

A year later, football coach Chris McMahon invited Wooten to join his staff. Wooten said he wasn’t a “football guy” to which McMahon replied, “That’s perfect. We have enough guys who know football. I need a coach.”

Wooten works with the freshman and JV teams and keeps statistics for the varsity. He took a crash course in football while the learning curve for baseball, a sport of which he’s always been a big fan, wasn’t as steep.

“I didn’t play it, but it’s baseball,” said Wooten, who still resides in his hometown and works in special education at Grafton Middle School. “Throw the ball, catch the ball, hit the ball. It’s pretty easy.”

Wooten credits the coaches he has worked for, a group that also includes Joe Tosches (L.J.’s dad), Mike Coonan and Brian Andersen in baseball, and Mike Binkowski and Brian Lehtinen in hockey, for his development on the fields and in the rink.

“You learn a little bit of something from everybody, and it just makes you a better coach,” he said. “Absorb it all and just take it in.

“It’s a lot of time that I invest in this, and I love it. Everything is for the kids.”

Plenty of three-sport coaches throughout Central Mass.

The T&G reached out to high school athletic directors across Central Mass. requesting them to send us any three-season coaches who work in their district, be it as a head coach or assistant at the high-school or middle-school level. Here’s a list of the dedicated individuals we received:

—Contact Rich Garven at rgarven@telegram.com. Follow him on X, formerly known as Twitter, @RichGarvenTG.

This article originally appeared on Telegram & Gazette: 'Not a lot of free time, but I love it': Here are five high school coaches for all season, devoted year-round mentors