Friday, December 19, 2025

Windham High grad continues giving back to community through coaching

By Matt Pascarella

Windham High School 2023 graduate Alex ‘Bob’ Wing is just one of the many post-WHS athletes who have gone on to make contributions to the up-and-coming group of young athletes and to work to instill in them the values that they have learned throughout their time on various teams.

Coach Alex 'Bob' Wing a 2023 Windham High graduate,
celebrates with his JSMS boys' basketball team during a
game against Sacopee Valley at Jordan-Small Middle
School in Raymond on Monday, Dec. 15.
PHOTO BY MATT PASCARELLA  
 
Wing has been coaching with his older brother, Andrew for three years at Jordan-Small Middle School and last year was the first year that he coached soccer, basketball and baseball solo. Bob Wing has worked at his family’s restaurant, The Beacon, in Raymond since graduating from Windham High.

“Andrew asked if he wanted me to give him a hand coaching the boys’ sports at Jordan-Small Middle School,” said Bob Wing. “I hadn’t thought about coaching, but after I decided not to go to college, I thought it would be good for me to try something and see if I liked it. It’s a lot of fun, (Andrew and I) talk a lot about how each team is doing, games are fun because we’re doing it alongside one another – it’s been really cool.”

It’s fun for Bob Wing to watch the kids he coaches grow and improve. He enjoys coaching the various teams at JSMS.

“I think Bob is a pretty good coach,” said JSMS seventh grader Charlie Crowell. “He makes smart decisions. He tries to make the practices fun and the drills we run are usually fun. He makes jokes so the practices aren’t super serious.”

Playing for a variety of travel teams with all kinds of coaches let Bob Wing see many different coaching styles. That has helped him figure out how to approach his players and work out who he wants to be as a coach and how he wants to approach coaching.

JSMS eighth grader Eli Delude said Coach Bob Wing is very good at keeping them on track but also knows how to keep it fun. He said his practices are always productive and no time is wasted.

“If you do not know exactly what you want to do right out of high school, that is not the end of the world,” said Bob Wing. “Sometimes it takes some time to figure out what you want to do in life.”

While there are many definitions for success Bob Wing defines it as being there to help people get to where they want to be, to help them make the right decisions.

Bob Wing may help out Windham’s varsity baseball program this spring as an extra hand on the coaching staff.

“He lets us do scrimmages at the end of practice so that’s always fun,” said JSMS seventh grader Brecken Cressey. “He’s a five-star retrograde coach and he’s a fan favorite.” <

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