WINCHESTER — There were no Super Bowls or Middlesex League Liberty titles, but to look back over the last decade, the Winchester High football team had some pretty good players that made for an exciting team to watch.

The Sachems had an excellent string of quarterbacks through the decade, making it the toughest position for head coach Wally Dembowski and his staff to narrow down.

In fact, Winchester’s first-team defensive secondary would make for a pretty potent aerial attack with Liam Fitzpatrick throwing to Davis Clarke, Jakob Flores and Sam Casey.

To the victors go the spoils, and the 2019 team was rewarded for going further in the playoffs than any of the squads earlier in the decade. Tommy Degnan earned first team at both quarterback and middle linebacker.

Degnan scored four touchdowns against Woburn on Thanksgiving Day in a double overtime win in 2018. Then last fall he ran for over 1000 (1,046) and passed for over 1000 (1,118).

Running back Jimmy Gibbons still has his senior year to play, but is being rewarded for already having three highly-productive years as at running back.

The Sachems use the spread offense so the coaches were able to spread out their choices to four per team, and Winchester had the players to fill them. Henry McDonough had the best single season ever when he got healthy for the first time and became the No. 1 target for Fitzpatrick, who had a career year as a junior before having his senior year hindered by a knee injury on opening day.

The late-Pat Gill was on his way to finishing a four-year career as a top receiver and team leader in multiple sports when his life was cut short by a terrible auto accident during his senior year in 2014. His memory is still an inspiration for Winchester varsity athletes several years later.

The defense is led by defensive end Joe Lepore, who was a three-year force on both sides of the line. Tommy Degnan was Tommy Degnan at linebacker, and Parker Carey was a quiet tackling force, also at linebacker.

The second team was headed by another star quarterback in Michael Grassey, who doubled as an equally impressive star of the basketball team.


2010’s All-Decade Team



QB — Tommy Degnan

RB — John Costello, Jimmy Gibbons

WR — Henry McDonough, Pat Gill, Stephen Fitzpatrick, Matt Romagna

OL— Dan McGurl, Mike Conley, Joe Lepore, Brendan Gill, Devin DeVincenzo


DL — Joe Lepore, Lars Zandbergs, Cam McGhee, Adam Johnston

LB — Tommy Degnan, Parker Carey, Billy Miller

DB — Davis Clarke, Sam Casey, Liam Fitzpatrick, Jakob Flores



QB — Michael Grassey

RB — Peter Gallagher, Timmy O’Brien

WR — Quinn Johnson, Henry Kraft, John Dooley, Evan Clarke

OL — Teddy Falkenberg, Teddy Lang, Bobby Hyers, Jimmy Crowther, Matt Olivier


DL — Aria Manfred, Christy Redler, Stefan Zandbergs, Sam Ducharme

LB — Teddy Centofanti, A.J. Abbanat, Brendan Curran

DB — Max Ward, Joe Ntege, Stephen Osborne, Patrick Costello

Honorable Mention: Tim Mangano, Andrew White, Dana Marrocco, Joe Fallon, Tony Oquendo-Loftman, Matt Carr, Ken Crotty, Joe D’Amico

• Winchester High football coaching staff assisted in the compilation of this list.

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