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The Winchester High football team might have fallen short of its ultimate Gillette Stadium goal, but there was still plenty to celebrate.
The Red & Black, the fourth overall seed in Division 2, racked up 11 wins, including two in the playoffs, before dropping their only game of the season to top-seeded Catholic Memorial in the state semifinal round. They then bounced right back to double up host Woburn in the annual Thanksgiving Day game, 28-14. It was their second straight win over the Tanners, and now lead in the overall series, 57-55-12.
The high-powered Winchester offense ended up scoring 450 points in 12 games, while the defense only gave up 160. After all of that, the Winchester boys were able to win the program’s first Middlesex League title since 1990.

“We exceeded most of the (goals) that we (had lined up for ourselves) coming into the season regarding the overall (offensive) numbers,” said Coach Wally Dembowski. “We were unsure of replacing three offensive line positions, but (their replacements) all produced at consistent, fantastic levels. The offensive production allowed our defense to be aggressive and attack.”
Three of the team’s dynamic offensive stars are seniors, and they all turned in one last memorable performance on Thanksgiving. Nicky Rotondi was the leading rusher with 167 yards on 24 carries, Ted Budreski caught six passes for 162 yards and four touchdowns. Quarterback Ronan O’Connell completed 12 passes out of 19 attempts for 230 yards, four of which went for touchdowns to Budreski.
On defense, senior lineman Chris Russo, filling in for injured captain Bryan Harrison at middle linebacker, collected five solo tackles and assisted on four others. Senior lineman Shaun Garrett was credited with three tackles. Senior defensive back Quinn Pimentel had three tackles, one for a loss, and he also helped out on another one. Rotondi, playing linebacker, had four solos and teamed up for another one, while also breaking up a pass to prevent another long drive by Woburn. Senior cornerback Will Nelson was responsible for four tackles. Junior defensive back Will Bolognese intercepted one pass – his sixth this season – and also had three tackles.
By the numbers
Senior captain Gianni DePrimeo was the team’s leading rusher this year with 1.702 yards on 161 carries, while also establishing a new school record for touchdowns with 25.
Summing up the season, Dembowski has no complaints.
“The season was fantastic,” he said. “Our 11 wins this year tied a school record, and the players worked extremely hard to get the job done, while the coaches were able to push them past their comfort levels. One of our goals this year was winning the league. Done. Another one was to go deeper in the playoffs beyond the quarterfinals. Done. Thanksgiving was another goal. Done. We also wanted to win the Super Bowl, but CM unfortunately got in the way.”
Dembowski said that this group was his most accomplished team in the last three years, with many of these same players suiting up for the varsity in each of those seasons. Among other things, the Red & Black secured their first Middlesex League title in 35 years.
“That was an awesome way for these seniors to end their high school football careers. They just missed winning the league title in each of the last two seasons,” Dembowski said. “It will be hard to replace these 25 seniors on this year’s team, because they each contributed something (positive) to the program the last four years.”
The veteran Winchester coach compared this year’s team with its 2019 counterparts, who were also really competitive, albeit with heartbreaking results. They lost to Tewksbury in the Division 2 quarterfinals by one point, before missing the league title by one game.
But the coach remembers that squad beating Woburn in the 2018 Thanksgiving Day game in overtime, despite the below zero temperatures, which set them up nicely for 2019.
Comings and goings
“The bar has been set extremely high for next year’s returnees, who will have to work hard to prepare for each opponent's best effort,” said Dembowski.
Sophomore Nolan Byrne, coming off knee surgery, will look to fill the running back void without the likes of DePrimeo and Rotondi around.
Peter Alexopoulos is slated to be next year’s signal caller. But he already has varsity experience, having seen some time behind center the last two years.
Dembowski, however, admits that he and his coaching staff need to find four offensive linemen to fill out next year’s group of blockers, and it also won’t be easy to replace wide receivers Ryan Martin, Will Nelson and Budreski, plus captain Mike Ficociello at tight end. His sophomore brother Joseph could be slotted nicely into his spot.
If there are holes on offense, the defense will also be on “high alert” without Harrison at middle linebacker, according to the coach, not to mention William Mango and Pimentel at outside linebacker, Budreski and DePrimeo at cornerback and Rotondi at strong safety. The coach will also have a whole new defensive line in 2026.
Dembowski expects that the special teams should once again be reliable next year, led by Bolognese, the team’s trusted placekicker and punter. Long snapper Cole Deason is also coming back. Andrew Haigis, Eddie Sim, Jack Lennon, Ben Adams, Evan Berg, Mike Beauvais, Henry Nagler, Dominic Vozzella and Patrick Winn are expected to step up as the team’s veterans next year.
Awards season
The Red & Black got together one last time on Saturday morning (Dec. 6) for a team brunch and awards ceremony to celebrate this memorable season.
Harrison was the recipient of the coaches’ award. The Doc Hines Lineman Award went to Lucas Sekino and Shaun Garrett, which was voted on by the players. The Mr. Provizano Award for team spirit was given to DePrimeo. This too was voted on by the players. DePrimeo was also the Liberty Division MVP in the Middlesex League. He joined Harrison and O’Connell on the All-League squad, as well. To cap off his league honors, DePrimeo was a league all-star, along with teammates Russo, Harrison, Budreski, Bolognese, Sekino and O’Connell.
As a result of these league awards, all of these players were presented with either trophies or certificates in recognition of their extraordinary seasons following the Saturday Brunch.
Joe McConnell is a longtime, award-winning sports editor for numerous North Shore publications. He began covering Winchester sports for the News last November.