For Jack Cheshire, it’s always been about the winning tradition of the Sayville football program. He was never consumed with his standing among the long line of elite quarterbacks that have performed in the program.
Record breakers such as All-Long Island standouts Chad Smith, Mike Buck, Dillon Boos, Steven Ferreira, Zach Sirico and Jack Coan, who is currently the starting quarterback at Notre Dame.
When asked about his contributions he always preferred to talk about his talented receivers and the way they executed pass routes. He talked up his offensive line and the protection and time afforded to find open receivers. He credited his coaches for what he called ‘can’t miss’ game plans. This is Jack Cheshire, who ultimately put his stamp on the last two seasons of championship football at Sayville.
Cheshire will stand among the Sayville greats with his own lofty stats -- two Suffolk Division III championships and the record for most touchdown passes thrown in a single season with 43 in his junior year.
In the shortened spring season during the COVID pandemic Cheshire was brilliant. He passed for 1,519 yards, completing 103 of 159 passes and 17 touchdowns while leading the Golden Flashes to a 6-0 record and the Suffolk Conference III title with a 32-7 win over Westhampton Beach. He passed for one score and ran for two others as Sayville won a Suffolk-record 15th county championship.
For his accomplishments, Cheshire earned Newsday’s 61st Carl A. Hansen Award, presented to Suffolk’s most outstanding football player. The other finalists were Leisaan Hibbert of Half Hollow Hills East and Ka’Shaun Parrish of Bellport, two fantastic two-way impact players.
Cheshire also earned the Boomer Esiason Award, given to Suffolk’s top quarterback.
"He has great vision down the field and he understands all the concepts of our offense," said Sayville coach Reade Sands. "He had the ability to break down coverages and make the right pre-snap reads. It became an excellent student of the game. He did exactly what we told him to do. And perhaps, the most impressive part of his game was watching him develop and move around the pocket and find people in open space and make incredible throws."
Cheshire threw for 4,733 yards and 60 touchdowns in only two years. He completed 65% of his passes.
"He didn’t even start on our junior varsity as a sophomore," Sands said. "He was splitting time with our tight end Jack Pierce. But he had an unbelievable off season and became the starter as a junior."
Cheshire enjoyed two defining moments in his senior campaign. He completed 19 of 28 passes for a school record 500 yards and five touchdowns in a 47-21 win over Westhampton Beach in week two of the regular season.
And he added to his legacy when he led the Golden Flashes in an epic non-league showdown against Floyd, Suffolk’s defending Division I champions, in an atmosphere likened to a Long Island championship game. In a dream matchup come to life, Cheshire engineered a 24-0 dismantling of a Floyd team that went on to win the Conference I crown. He completed 21 of 35 passes for 253 yards and a score in a game that proved schools of smaller enrollment in certain years could compete against the larger schools.
"We had a third down and 13 with two minutes left in the half against Floyd and he made the play of the game," Sands said. "He moved around the pocket and hit our tight end Jack Pierce on a 15-yard pass for a pivotal first down. He scored on a six-yard run a few plays later for a 14-0 lead and it was a big moment."
For the first time since Suffolk went to four classifications in 1992, two champions met on the field, and Cheshire was the difference.
"He is an incredible quarterback," said Floyd coach Paul Longo. "He’s a difference maker. We thought we had him trapped a few times in that game and he escaped the pressure and made a play – that’s a special kind of player."
Sands said Cheshire separated himself from the competition because he had an easy time processing play calls and understood what was going on all around him.
"In the championship against Westhampton they took away the deep pass," Sands said. "We dinked and dunked short passes and ran the ball. He hurt people in different ways. The deep ball, the run, he could do it all."