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After serving as a varsity assistant and the JV head coach the last three years, Katelyn Flanagan recently began her first season as the head coach of the Old Saybrook High School softball squad. Katelyn works as a physical education teacher at Old Saybrook Middle School, where she’s also a cross country coach. Photo courtesy of Katelyn Flanagan

After serving as a varsity assistant and the JV head coach the last three years, Katelyn Flanagan recently began her first season as the head coach of the Old Saybrook High School softball squad. Katelyn works as a physical education teacher at Old Saybrook Middle School, where she’s also a cross country coach. (Photo courtesy of Katelyn Flanagan )

Flanagan Aims to Take Rams’ Softball Back to the Big Time

Published Apr 20, 2017 • Last Updated 12:36 pm, April 20, 2017

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As the Old Saybrook softball team tries to bounce back from its two-win season and begin the climb back toward playoff prominence, it’s doing so with someone who’s a familiar face to the Rams. That person is Katelyn Flanagan, who recently began her debut campaign as Old Saybrook’s head coach.

Katelyn, a lifelong Waterford resident, helped the Lancers’ softball squad win the Class L state title in her senior season of 2009. Following her time at the University of New Hampshire, Katelyn took a job as a physical education teacher at Old Saybrook Middle School and later became a cross country coach at the school—a position she still holds today.

After spending the last three seasons as a varsity softball assistant and the JV coach at the high school, Katelyn takes the reins as Old Saybrook’s varsity head coach this spring. She picked up her first victory when the Rams defeated Portland 23-2 on April 5.

“I got the teaching job in Old Saybrook, and it’s sort of an unwritten expectation that you are expected to coach as a physical education teacher,” says Katelyn. “In my first year teaching, there happened to be an opening with softball, I hit it off with [former Rams’ Head Coach Laura Westner], and here I am now three years later. It’s been an exciting transition.”

The transition has proved a pretty smooth one for Katelyn and her athletes. One of the biggest reasons is that Katelyn already knows many of her players from teaching them before they arrived at the high school and then coaching them in both the JV and varsity ranks once they got there.

“There are an amazing group of girls here. I taught most of them when they were in middle school, so there is that sense of trust there, which is a big benefit,” Katelyn says. “It’s also key to them buying into what we want to do here. It’s actually been an easy transition for everyone.”

Katelyn wants her Rams to show up to the field every day ready to put in the hard work that’s needed to succeed both individually and as a team. However, Katelyn doesn’t necessarily want them to view it as work because it’s important to her that her athletes develop a love for softball.

“I want to get the kids passionate about the game, while trying to get them to compete at a higher level and teaching life lessons. I want to make sure softball is fun for them. I know I can get a lot more out of them when they are enjoying the game,” says Katelyn. “I want to get them motivated to play for the team and each other. We are coming off a 2-18 year, so I want them to know how to compete when they are both down and up in a game.”

A true teacher, Katelyn loves those instances when something clicks for her athletes in either practice or the heat of a contest and makes them enjoy the sport that much more.

“I love seeing kids have that a-ha moment. It’s rewarding. It’s similar to teaching,” she says. “I love seeing both the individual and the team succeed. I love seeing them carry out the things you teach in practice during a game.”

Old Saybrook Athletic Director Michael Cunningham feels that Katelyn is a cut above the rest in terms of her dedication toward both coaching and teaching. Cunningham also appreciates the level of respect that Katelyn displays to her pupils.

“Katelyn was an easy decision to appoint as the head coach for our softball program. In the short time I have been here, she has been a wonderful person to work with in the [physical education] department,” Cunningham says. “Katelyn pours her heart into working with our student-athletes each day. Her practices are organized, and the players are engaged and developing each day. Katelyn is the utmost professional and I hope our parents and athletes know how lucky they are to have her on our team.”

As she takes over a program that’s seen some peaks and valleys the last few years, Katelyn knows that Rome certainly wasn’t built in a day. She wants the Rams to make incremental progress and take it one achievement at a time as they try to work their way back to the big time.

“In the short term this year, we have our goal of eight wins and getting to states this year. The captains also set this goal, and I have all the confidence in the world that we can reach it. For me, I want to see improvements in them every day,” says Katelyn. “In the long term, we want to be the team to beat. Three years ago, this team went to a state final. We want to be a top contending team. We can get there in the next couple of years. We are taking baby steps and striving for improvement.”

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