It wasn’t too long ago Jack Cheshire was in the stands watching Sayville-great Jack Coan throwing touchdowns and winning games, hoping to one day see himself in the same situations. The senior quarterback didn’t have to wait long, and on Friday night under the lights one last time, Cheshire capped off an illustrious career that just might make this star shine brighter than the rest. He scored two touchdowns on the ground and one in the air in Sayville’s 32-7 win over Westhampton Beach for his second straight Suffolk County Division III championship. It was the record 15th title in school history, which also capped the sixth undefeated season for the Golden Flashes.
“Just dreaming about being in this situation and to finally be here — there’s no better feeling,” Cheshire said. “Going from not even starting on the junior varsity team as a sophomore to Coach [Reade] Sands trusting me and putting the ball in my hands as a junior is just the best feeling in the world.”
Sayville (6-0) was up 7-0 early, but it wasn’t until Max Llewellyn’s safety with 4:34 left in the first half that the Golden Flashes really got things going. Just one minute apart, Cheshire scored back-to-back touchdowns on keeper plays, the most in his short varsity career. At 3:10, he carried the ball 5 yards for a touchdown, and after a Charlie Sands blocked punt helped Alex Millwater (109 yards rushing) take the ball to the 4-yard line, Cheshire ran in his second from 2 yards out for a 22-0 halftime advantage.
“I owe it all to my teammates. They have my back every single time,” Cheshire said. “The grit and the energy that we had on the field was unmatched. Seeing everyone rally to the ball and making these plays is ridiculous — it’s awesome.”
Junior kicker Michael Argenziano, who was perfect on the evening, hit a 35-yard field goal to make is 25-0 in the third before Westhampton Beach (5-2) got on the board with a Gavin McIntyre 20-yard touchdown run with 2:03 left in the third. Cheshire found senior wide receiver C.J. Messina on a 5-yard pass for the final touchdown of the game early in the fourth.
“Today we knew we couldn’t take any plays off,” Messina said. “We knew we were going to have to come out playing physical and tough, and that’s exactly what we did. We had to go 110 percent every play and had to give our last game everything we had, and I’m so proud of how hard everyone played today. There’s a lot of pride and tradition here in this brotherhood.”
That’s exactly what Llewellyn, a senior guard who finished the game with a team-high four tackles, spoke to in the huddle with his teammates following the win.
“I’ve been on a lot of teams and played with a lot of guys, played against a lot of guys — there’s no group like this one. This is my favorite team,” Llewellyn said. “Every single guy brings it every single day. That’s why I love you guys. That’s why we’re champions.”
While Cheshire hasn’t played with as many, he didn’t need to to come away as one of Sayville’s best quarterbacks. As a junior he threw a record-breaking 41 touchdowns on the season in the Suffolk County title game, surpassing the Long Island record of 40 set by Coan in 2014. He finished that season with 43. He also became only the second player in Long Island history to throw for more than 3,000 yards in a season, again joining Coan, who passed for 3,431 yards that season, while Cheshire threw for 3,226 in 2019. This year, Cheshire passed for five touchdowns and a school-record 500 yards in a 47-21 win during the first meeting between his Golden Flashes and Westhampton Beach. But more than personal records or accolades, Cheshire said it’s the success of the team and the bonds he’s created that’s mattered most.
“We just play together, and that’s really what separated us. That’s what makes us the number one public school in the state,” Cheshire said. “These are my best friends, they’re my brothers. We’ve been dreaming about this since we were little kids, and we’re here now. We prepared and prepared and prepared for this. We anticipated, and we played with confidence. I’m going to miss playing with these guys every single day. “This has been the best time of my life.”
