The Westbrook Knights boys’ basketball team announced its new head coach for the 2023-’24 season on Aug. 16. Alan Stekloff will be leading the Knights as their head coach with Trevor Phelan as the new assistant. Alan has plenty of good reasons on why he decided to join the Knights.

“I had coached many years for both boys’ and girls’ basketball, both the college and high school level. When COVID hit, I stopped coaching, and last year I was called back to coaching at Old Saybrook as their assistant,” says Alan. “When Westbrook’s job opened up, I really liked the idea at a small town. I really love a small-town atmosphere and love Westbrook. The facilities are great, and the people are outstanding.”

Alan brings extensive coaching experience to Westbrook. He began coaching for the Portland Highlanders as the assistant boys’ basketball coach. From 2006 to 2008, he served as the assistant women’s basketball coach at UConn Avery Point. In 2013, Alan was hired as the Hamden Green Dragons girls’ basketball coach and coached there for four seasons. Alan built the program up to a playoff team and returned Hamden to a place of prominence in Southern Connecticut Conference.

Caitlin Eichler, the Athletic Director at Westbrook, talks about how Alan will positively impact the Knights for the upcoming season.

“We are excited to have Coach Stekloff join Westbrook’s coaching staff. He brings years of collegiate and high school coaching experience. His coaching style fosters team building, skill development, and positivity,” says Eichler. “Coach Stekloff has experience building successful programs, as well as familiarity with the Shoreline Conference [SLC], which we are looking forward to.”

Eichler adds that the Westbrook community is excited to have Alan on board to lead the Knights as their new head coach for the 2023-’24 campaign.

After coaching at Hamden, Alan returned to Portland as its head coach. Now coming back to basketball as Westbrook’s head coach, Alan elaborates on his hopes for this season.

“I have coached against Westbrook, and the kids at Westbrook have always been hard-working. I have never coached against them where they were not,” says Alan. “In Class S basketball, Division V, you are very limited. One thing that I have noticed from Westbrook from an outsider’s point of view—the kids work hard, they are always respectful, dedicated. I really look forward to coaching the team.”

Last season, the Knights finished their season with an overall record of 2-18 and a mark of 1-16 in the SLC.

“In terms of wins and losses, not knowing what the season will bring yet, I guarantee the kids and myself will work hard every day,” says Alan. “[Former Head Coach Jeff Beeman] was a great coach. He has left behind good, hard-working kids.”

Alan notes that he was able to meet a few of the players he will be coaching this season during his interview process at Westbrook. Alan will be coaching alongside Trevor Phelan, who he has coached against throughout the past few years.

“I coached against him last year during the freshman game, and I know he played in the SLC. He is very well-regarded by the student athletes and the athletic director administration,” Alan says of Phelan. “It is a win to keep on someone on the staff who is young, energetic, wants to improve. I am looking forward to coaching with him.”

Eichler believes that Alan and Phelan will form a terrific tandem for the Knights.

“Coach Stekloff and Coach Phelan will be a dynamic duo. The two of them will be able to connect with our athletes on different levels. Coach Phelan already has knowledge of the athletes and will continue to grow as a coach under Coach Stekloff,” says Eichler. “The two have similar coaching styles and philosophies which will complement one another. We are looking forward to a season of growth and success.”

Although the winter campaign has yet to begin, Alan notes a few challenges that the Knights will be facing as a smaller team this season.

“One thing that is great about high school athletics is at some point you are going to face some challenge or adversity—you just do not know what it is all the time, whether that be on the court, during practice, could be in school itself. How we learn—we grow and face those challenges,” says Alan. “Challenges always being when you are in a small school, facing bigger schools, how do you make up for not being the tallest or fastest team? That is why developing that work ethic will meet any challenge when it does arrive.”