Not long after Tyler Wosleger relinquished his duties as head baseball coach at Hotchkiss School to accept the same position with Westminster School back in 2020, one of the first things he thought about was his father.
When Scott Wosleger was put in charge of the Choate Rosemary Hall School program in 2017, he and his son were quickly drawn into a fierce, competitive rivalry as members of the Founders League. Following Tyler's move to Westminster, another Founders League representative, the duel continued.
Tyler, along with brothers Owen and AJ, all played high school baseball for their father when he was head coach at East Hampton (Conn) High School from 2008 to 2014. The eldest Wosleger had a successful campaign during his time there, winning three Shoreline Athletic Conference titles and a CIAC state championship in 2011. Last month, he was inducted into the East Hampton Sports Hall of Fame.
Once settled in at Westminster, Tyler began toying with the notion of having his father coach with him instead of against him. But at the time, it was nothing more than mere conjecture.