Thursday, October 1, 2026
From the moment the game was announced, the Long Island football community has been abuzz.
Throughout most of the summer, it felt like the highly anticipated crossover game between Massapequa and Garden City, a clash of champions at Hofstra’s Shuart Stadium on Sept. 26, was the only thing talked about.
That is, by everyone but the Massapequa players. Well, except for the first day of summer workouts.
“We’re shutting that down right now,” Chiefs head coach Kevin Shippos told his team that day. “I said, this is the only time I’m going to talk about this is right now. I said I don’t want to hear a word, and they haven’t said a word the entire summer.”
The interest is understandable. Massapequa is a three-time defending Long Island Class I champion taking on a Garden City team that has a 66-game winning streak, the longest in the nation.
But for Massapequa, the focus is on Port Washington in Week 1.
“Obviously, it’s a big game, but we’ve got a monster opening game with Port Washington, and that is a huge threat,” Shippos said.
While the Chiefs graduated a bulk of their key skill players last year, they do return standout quarterback Luke Garguilo, who, like his predecessor Joey Diesso, won the Don Snyder Award as Nassau’s top quarterback.
“He’s a gamer, one of the hardest workers I’ve ever coached,” Shippos said. “He takes everything very seriously, and he doesn’t need to say much around the guys. He just has a commanding presence.”
After having a complementary role last year, Dylan Milio is slotted in as Massapequa’s top receiver this year. The senior has been “lights out,” according to Shippos, in 7-on-7 play this summer.
“Having Dylan as a deep threat now is going to force teams to respect him and not be able to just load the box to try to stop a Luke or any of the other guys,” Shippos said.
Jason LaRosa, Casey Gilchrist, Dom Antonelli and Mike Ippolito will all feature in the receiving corps, while running back Mike Castellano is up from the junior varsity and Giovanni Tarasi and Justin Farrell will feature as tight ends.
Nolan Wieczorek and Jack Mulligan are returning starters who will anchor an offensive line that does have some inexperience.
“They’ve been working hard, but that’s where we’re going to have to play at a high level to get these skilled guys involved,” Shippos said. “We’ve been preaching all summer and the first two practices: We don’t go anywhere unless we get a push up front on both sides of the ball.”
Mulligan and Ryan Chabus are also returning starters on the defensive line, though Chabus’ impact came in the second half of the season last year.
“He really was a spark for us last year when we had some injuries,” Shippos said. “When we moved Jack from defensive end to defensive tackle, and then put Ryan at end, it really solidified us up front.”
Wieczorek will be the leader of the defense at linebacker, joined by Tarasi, a fellow returning starter, while Aiden Carozza, who is up from the junior varsity, will likely fill the third linebacker spot.
In the secondary, Milio and Ippolito are returning starters at each corner.
“They give us an advantage on the outside where we don’t necessarily have to put a safety over the top,” Shippos said. “We can go one-on-one and feel good, with them being able to single-cover anybody’s receiver. Both of them are great kids, super talented, great effort, great attitude, just great leaders.”
Expectations are sky-high for the Chiefs, 35-1 over the last three years and the No. 1 preseason seed in Conference I. But that’s nothing new in Massapequa, even if some of the names are different.
“It’s a good mix between established, veteran players and some youthful, inexperienced, but eager to learn and get better,” Shippos said. “You’re never gonna have 11 starters back on both sides of the ball. That’s the fun part about coaching. Every team is different.”
To read more from the Herald's 2026 High School Football Preview, click here.
