Today’s question: Who are the 11 best North Shore head football coaches of the 21st century? Phil Stacey and Matt Williams pooled their thoughts and came up with one definitive list.
1. Dave Woods, Bishop Fenwick (1998-present). The only man to have ever remained at the helm of his program every season of this century to date, Woods is a certified North Shore coaching legend. Under his leadership, Fenwick has been to three Super Bowls since the turn of the century (winning in 2000 and 2013), had two perfect seasons (2013 and 2021 Fall 2), and his teams are perennially in the title hunt. Adept at changing to the personnel he has in a given season and not afraid to think outside the box in an attempt to cross opponents up. Sports a 198-93 record and three Super Bowl crowns overall; he’ll win his 200th career game sometime next month.
2. Paul Ingram, Gloucester (2003-2010). The excellence that Ingram’s teams put into his relatively short span as head coach of the Fishermen is simply remarkable. Gloucester lost just 10 of 94 contests where Ingram had the final say, finishing with three perfect seasons and winning a Super Bowl crown in each. They won four Northeastern Conference titles, just missed out on two others, and went an unfathomable 50-2 over his final four years. Needless to say, he was the architect of the greatest era in GHS gridiron lore.
3. Jim Rudloff, Marblehead (2009-present). Took what had been a moribund program and changed it into a state powerhouse, reaching heights the Magician gridders had never quite seen before. Became the fastest North Shore football coach to 100 career victories (128 games), a record that’s likely to stand for a long time. Even more remarkable is that MHS had won exactly 26 of their previous 125 games before he took over. Owner of 11 Northeastern Conference titles, three Super Bowl appearances and an unbeaten championship season in 2021. Put respect on the man’s name.
4. Brian St. Pierre, St. John’s Prep (2014-present). When St. Pierre finally decides to hang up his whistle far down the coaching road, he could very well be the first name that any 21st century North Shore high school football conversation begins with. The Eagles always have talent in the system, but St. Pierre has made the program full of sandpaper, grit, and even some nasty. It’s been a ridiculously successful formula; St. Pierre’s teams have won 82 of his first 112 games, been to four Division 1 Super Bowls and captured three (2018, 2019, 2022). Those championship numbers will expand in the years ahead.
5. Jim Pugh, Masconomet (1989-2014) and Hamilton-Wenham (2016-21). Having taken a down-and-out Masco program and transforming it into a Cape League power in his first 11 years isn’t factored into this exercise, but no matter. Pugh, the third-winningest football coach in area history, piloted the Chieftains to seven CAL crowns and two Super Bowl appearances, then won two more league titles with H-W. Always able to see the big picture, Pugh knew when to push down on the throttle with his players and when to ease up. Was a combined 156-79 in his two coaching stops from 2000-21, giving him a career mark of 216-132 over 32 seasons.
6. Steve Dembowski, Swampscott (1999-2014). Think for a minute: how many high school coaches in any sport have ever completely changed the way the game was played? Because that’s what Dembowski did when he brought the spread offense to his alma mater in 2001. Yardage, points, and most importantly wins piled up for the Big Blue in pinball-like fashion, resulting in four Northeastern Conference titles and a Super Bowl title in 2017. Went 110-61 at Swampscott this century (114-67 combined) before moving to coach his adopted hometown of Milton, where he’s had similar success (77-21 and coming off a Super Bowl championship last fall).
7. Dan Bauer, Beverly (2003-15). If there were a Mount Rushmore of Beverly football coaches, Bauer would be on it alongside Charlie Walsh, Roy Norden and Bill Hamor. A rare ‘outsider’ (from Missouri, who played Ivy League ball at Penn) to be given the keys to the program, he led the Orange-and-Black to seven or more wins in nine of his final 11 seasons, including its first-ever Super Bowl title in 2010. Two years later, the Panthers had the greatest season in school history, going 13-0 and taking home another state title. In a spread world, his teams went back to the Wing-T offense to great success. Physical toughness was also a trait of Bauer’s teams.
8. Jim O’Leary, St. John’s Prep (1984-2012). We’re only factoring in the 21st century here, so O’Leary could go on the list for the mere fact that his squads won nearly two-thirds of the games (101-55) they played under him from Y2K on. That includes three straight Catholic Conference titles from 2001-03 and a shared crown in 2004, no small feat in the state’s best league, plus a Super Bowl title in 2012. O’Leary surrounded himself with good people on the sidelines to keep the Eagles in contention year in and year out. In a 30-year career he finished with a 207-106-2 mark.
9. Mike Flynn, Pingree (2018-23). The former Baltimore Raven lineman came to ‘The Farm’ and kept the still-young program in the rarified air it had become accustomed to. In just five seasons played — Pingree didn’t field a team during COVID — the Highlanders went 35-8-1, an excellent .815 winning percentage. They made four prep school bowl appearances in those five years, winning New England titles in 2019 and 2021. Tough like their head coach, Pingree also showed remarkable skill in the skill positions, giving them a perfect blend for on-field prosperity.
10. Ed Nizwantowski, Peabody (1982-2004). Yes, he only coached for five years this century, but that half-decade was a remarkable one for the Tanners. They won 41 of 50 games during that time frame (.820 winning percentage) under Nizwantowski, with nearly half (4) of those setbacks coming against the state’s best team at the time, Everett. Then consider the tailspin Peabody went in after his departure, winning just 25 times over the next nine seasons combined. He’s 174-59-2 all-time and deserves a spot on this list.
11. Chris Powers, Pingree (2006-17). Having started the football program at Pingree, Powers was the perfect pilot to lead it through its first dozen years. Not willing to go through a ‘learning’ phase early on, he got his players to buy into his system early on, saw more and more talent come to the school with each passing year, and winning became an expectation, not a hope, in short order. The Highlanders won back-to-back prep school bowl championships in 2009 and 2010 and played in four during Powers’ tenure, which culminated with a 68-39 mark.
