Westhampton football's Jake Calloway has hand in five TDs in win over East Islip
Quarterback Jake Calloway of Westhampton breaks through the defense to score in the first quarter of a Suffolk Division III football matchup against East Islip on Friday, Oct. 2, 2026 in Islip Terrace. Credit: Michael A. Rupolo Sr.
Westhampton Beach quarterback Jake Calloway has missed most of the past two seasons with injuries. A punctured lung in his sophomore season forced him to miss four games.
A broken clavicle ended his junior campaign in the first quarter of the season opener last year against Smithtown West.
And here was Calloway giving it all he’s got in his senior season, playing his last year of high school football, before he’s headed off to play lacrosse at Penn State.
Calloway’s full arsenal was on display Friday night in Islip Terrace. He had a hand in all five Westhampton Beach touchdowns in a 34-0 win over previously unbeaten East Islip in a Suffolk Division III game. He threw for two scores and ran for three more.
“We knew what we were missing,” Westhampton Beach coach Bryan Schaumloffel said. “He’s a special kind of athlete, a real game changer. He’s fun to coach.”
Westhampton Beach improved to 4-0 and East Islip fell to 3-1.
Calloway completed 4 of 5 passes for 149 yards and rushed for 104 yards on 11 carries.
“We have an unbelievable offensive line that put in the work in the offseason,” Calloway said. “And our defense is phenomenal. This is a group of friends that have played together for a long time. We won the PAL third grade championship with the same group.”
Westhampton Beach opened the scoring when Calloway rolled to his right, set his feet, and launched a long pass to wide receiver Connor Ragimierski. He hit the junior in stride for a 71-yard TD pass and Blake Schaffer added the kick for a 7-0 lead with 5:49 left in the first quarter.
“It was a perfect throw,” Ragimierski said. “We’re having fun out there.”
What made the throw more impressive was how Calloway rolled to his nonthrowing shoulder side of the field and still found the arm strength to get the ball to Ragimierski.
“I prefer to roll right even though I’m lefthanded,” Calloway said.
Westhampton extended its lead when Calloway went on a quarterback keep for a 26-yard TD run. Schaffer added the kick to make it 14-0 late in the first quarter.
Calloway pointed to the line play of tackles Prince Ivory and Blake Gilks, center Sonny Hebberd, tight end Andrew Lewis and guards Liam Brand and Jaedyn Cobb as the key to the offense.
“Our guys got stronger in the weight room this summer and it shows,” Schaumloffel said. “And the first-team defense hasn’t allowed a score.”
Calloway capped a seven-play, 60-yard TD drive with a 3-yard run to lead 20-0 at the half.
“I knew we would have our hands full with Calloway,” East Islip coach Sal J. Ciampi said. “He’s a special player.”
Coincidentally, the first game ever played by an East Islip varsity football team came exactly 72 years ago on the same date, Oct. 2, 1954. And guess who they played? It was Westhampton, who came into town and beat East Islip, 32-0 at the old East Islip High School on Main Street.
For Calloway, who has earned his place in the discussion for the Hansen Award, presented to Suffolk’s most outstanding player, the long bus ride back to Westhampton will be filled with cheer.
There is only one goal for these Hurricanes — and that’s a Long Island championship.
Gregg Sarra is Newsday's high school sports editor and has been on the beat since the mid-1980s.
