Jake played in the Rutland-Essex rivalry his sophomore, junior, and senior years. As one of the captains of the 1998 team, Jake led his team to a 26-21 victory over Essex and a state runner-up title. In the Essex game, Jake injured his hand badly and missed almost the entire first half. After getting medical clearance, he returned in the second half and threw three touchdowns including the winning touchdown with no time remaining on the clock. Jake was named the Gatorade Player of the Year twice and went on to be the star quarterback at University of Maine before playing professionally.