Brennan Steps Down from Softball Helm


By Kevin Eickman

On May 8 of this past softball season, the Lady Bucs played their final home game of the season. For the Milford seniors, it was their final home game as high school athletes. While the final game was a lose, it was difficult to find disappointment in the eyes of the Milford players. This has been a hallmark of Milford under the leadership of now former coach Sean Brennan. During his tenure with the Buccaneers Brennan only wanted two things from his players, to have fun and get better every day.

While coaching at Milford, Brennan consistently managed to do both. Prior to the game Brennan informed his players of his decision to step down, it was not an easy one. “It has been a great time coaching these girls this season,” Brennan said. “It would have been better to have gotten the win but it never has been about wins and losses. We don’t play to lose, but the real mission hear is to educate and I believe we have done that.”

In total Brennan coached the Bucs for seven years. The crowning achievement was winning the State Championship title in 2017. What started out looking like any other softball season with Milford starting the year with a 4-4 record, turned into a wild ride which saw Milford run off 14 consecutive wins. In the eyes of Brennan it was one of the most amazing things he has witnessed.

“That was such a talented group of young ladies and once they started rolling there was no stopping them,” Brennan stated. “Nobody could hit like we could, from the top to bottom of that lineup was incredible. It didn’t matter who was at the plate, they were an offensive threat.”

When asked why he felt now was the right time to step down Brennan said, “It just feels like the right time for me. I want to spend more time with my family. Time flies, my daughter Kayla will be getting married in a few years and Darby is down playing at Liberty so I would like to get down there and watch a few games. I basically want to take some time to concentrate more on my family.”

While Brennan coached seven years, they were not consecutive. That brief respite is one of the very few things that he feels a twinge of regret about. “I was feeling a bit worn down and felt like I needed a little break. The most difficult part for me was not being able to coach Kayla, it is something I look back on wish I would have done a little differently,” he said.

Milford Athletic director Ryan Winkleblech has enjoyed a great working relationship with Brennan and while he will not be coaching anymore, Brennan will still be around the fields. Announcing field hockey and filling in where needed. Brennan’s commitment to youth sports is what makes him a valuable asset to the Milford community. “He had a lot of passion for coaching high school athletes. He was a pleasure to work with as a head coach,” Winkleblech said. “He truly understood coaching athletics in a high school setting.”


Having covered Milford softball for many years I have been trying to come up with a way to sum up what kind of coach he was. Win or lose his interviews with me were all the same, analytically and positive. As I racked my brain to come up with an answer, it became obvious. Refer to rule number one, have fun. Thank you for the fun Gator.

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