Looking ahead to Friday’s huge Bay State Conference matchup at home against Walpole, Milton coach Steve Dembowski remembered how his father, Henry, would often say, “The show must go on.”
Henry Dembowski died Sunday from cancer at age 83. The Lynn Classical graduate was a beloved Drama Club teacher at Marblehead High, where he directed his troop to a state championship in 1985. He spent 30 years in public education, including stints as Marblehead principal, and superintendent of the school systems of Martha’s Vineyard and Pentucket.
While the method of competition differed, Steve Dembowski has been influenced by his father during his successful run at Swampscott (1999-2014) and throughout his revival of the Milton program the past seven years.
“[My father] would say I got my coaching skills from him,” said Dembowski, who was named the Patriots High School Coach of the Week after steering No. 16 Milton to a 42-6 win over Holliston last Friday.
“He was a dynamic educator and he had a great way of getting the best out of kids. He’s someone who when he walked into the room, you knew he was in the room. He set goals and lived life to the fullest. There was never an obstacle he couldn’t pass.”
After his retirement in 1992, Henry traveled the east coast as an educational consultant and mentored students and teachers until this past January. Dembowski recalls how his father, who lived in Swampscott for 55 years, used to patrol the stands with a top hat and fur coat while forging and maintaining his strong connections within the community.
Dembowski led Swampscott to a Division 3A state title in 2007 and recorded the second-most wins (114-67) in program history. Now he’s 57-16 at Milton after starting 3-0 this season ahead of a battle between the top teams in the Bay State’s Herget Division.
“Last Friday, [Henry] kicked me out [of his hospital room] and told me to go win the game,” said Dembowski. “I know he wants me [to keep coaching] and that makes it easier.”
“As I expressed to the team, now this is about them. It’s kind of a way to escape, by going to practice and continuing to develop this team.”
No. 17 Walpole (3-0) is coming off a 27-23 comeback win over Wellesley last Saturday, a momentum shift that coach Chris Sullivan hopes is a sign of positive progress at his alma mater. Last fall, his squad fell in overtime (13-7) at Natick, failed to convert on several scoring opportunities in a 24-10 loss to Wellesley, then lost (10-7) to Milton on a last-second field goal.
With 15 starters returning and 47 upperclassmen on the roster, Walpole has outscored opponents, 109-23, during an impressive start for a storied program that has recorded seven Super Bowl titles and 20 conference titles.
“That’s the type of win you want out of your program, where it’s not your best day, but you’re able to get back into it and eventually get the win,” said Sullivan, a 2000 Walpole graduate and member of the 1997 Division 2B Super Bowl champion team.
“Even last year, I thought we took a step forward, we just didn’t win those tight games. I knew we had something cooking with these guys. They’re a talented group. They have a goal and a mind-set that dates back to a lot of old Walpole teams. At times it reminds me a lot of my early years [coaching] when the kids were just so mentally tough.”
Sullivan became an assistant coach at Walpole in 2006 shortly after graduating from Worcester State, where he played offensive line. In his third year on staff, Walpole clinched another Division 2 Super Bowl title, with future Boston Cannons lacrosse player Ryan Izzo leading the way. In 2018, Sullivan was promoted to head coach.
This year the Wolves are led by senior tailback Andrew Falzone, who also captains the defense from his strong safety position. Defensive end Kamari Hughes, linebacker Matt Reynard,and two-way lineman Mike Frederick played key roles in shutout wins over Framingham (56-0) and Natick (26-0) to open the season, while receivers Jamal Abdal-Khalaq, Sean O’Brien, and Max Collins have been great targets for senior quarterback Corey Kilroy.
With former NFL quarterback Todd Collins serving as offensive coordinator, Kilroy has thrown eight touchdowns through three games, and he can also threaten defenses with his rushing ability.
Milton senior quarterback Owen McHugh is a similar dual threat who is off to a fantastic start with 649 passing yards, 187 rushing yards, and 13 total touchdowns. The UMass Lowell baseball recruit started at safety the past two seasons and took some varsity reps at quarterback behind three-year starter Chase Vaughan.
“I kind of look at both [quarterbacks] in the same light,” said Sullivan. “They’re great passers, but ultimately they’re both just really good athletes who can make plays. It’s going to a great matchup between the two of them.”
McHugh is still playing safety this year, so he will look to slow down Walpole’s versatile passing attack. When the Wildcats are on offense, Falzone will be tasked with organizing the Wolves’ defense to try and contain Dembowski’s creative spread offense.
While he calls Falzone “another coach on the field,” Sullivan recognizes the task is formidable when going up against a talented quarterback with an innovative high school coach calling the plays.
“[Dembowski is] always a little step ahead,” said Sullivan. “He came to Milton and brought that air attack and kind of transformed their program. He’s a great spread coach and his offense has evolved with RPOs and he always adjusts based on his personnel. It’s hard to prepare against, but we look forward to the challenge of playing them.”