Jason McLeod – Portland football

File photo

File photoPortland’s football team suffered an agonizing playoff loss a year ago, had to replace several key contributors and at the midway point of the 2022 season, found itself 1-3, but when the dust settled, the Bulldogs played for the Class B state title.

The Bulldogs were fortunate to have a great coaching staff, led by Jason McLeod, guiding them through choppy waters and while their title quest came up six points short, it was a magical ride.

For pushing the right buttons and keeping the Portland ship on course, Jason McLeod is The Forecaster’s choice as our Portland edition Fall Coach of the Year, of a boys’ team, for the second consecutive year.

McLeod, who was also named girls’ team Coach of the Year in the spring, played at Bonny Eagle and for a short time professionally overseas, was the head coach at Westbrook in 2005 and 2006, then spent eight years as an assistant at Windham before coming to Portland as an assistant to Jim Hartman in 2016. McLeod helped lead the Bulldogs to the state final in both 2016 and 2018, before taking over as head coach in 2019. After going 1-7 his first season, McLeod’s second year was wiped out by COVID. In 2021, Portland was undefeated until running into Marshwood in the regional final where it was humbled, 35-0.


This year’s team had its hands full with a lot of new faces in new places and the Bulldogs’ challenges were compounded by the loss of senior quarterback Sam Esposito in the season opener. Portland won that game, at Kennebunk, but then lost consecutively to eventual Class C champion Leavitt, perennial Class A contender Bonny Eagle and eventual Class A champion Oxford Hills. McLeod then inserted senior Kennedy Charles at ‘Wildcat’ quarterback and the Bulldogs hit their stride, winning four straight games to close the regular season, then downing Noble, Kennebunk and South Portland to reach the state final. Portland’s quest for its first title in 20 years resulted in a 20-14 setback, but there was nothing but pride in the aftermath.

“It’s probably the best group of kids I’ve been around my whole life coaching,” said McLeod. “Not just the football players they are and the things they do on the field, but for the men they are off the field. It’s been great being around them. Their resiliency was profound over the course of the season.”

Following the season, McLeod stepped down, citing the desire for more family time.

A season that could have wound up in the doldrums wound up one of the most memorable in program annals. A big reason for the Bulldogs’ success was due to Jason McLeod, our Portland edition boys’ team Fall Coach of the Year, in his swan song with the program.

Prior winners:

• 2021 Jason McLeod (Portland football)
* 2020 Brandon Salway (Waynflete soccer)
• 2019 Brandon Salway (Waynflete soccer)
• 2018 Brandon Salway (Waynflete soccer)
• 2017 Rocco Frenzilli (Portland soccer)
• 2016 Frank Myatt (Deering cross country)
• 2015 Jason Jackson (Deering football)
• 2014 Colin Minte (Cheverus soccer)
• 2013 Rocco Frenzilli (Portland soccer)
• 2012 John Wolfgram (Cheverus football)
• 2011 Brandon Salway (Waynflete soccer)
• 2010 Rocco Frenzilli (Portland soccer)
• 2009 John Wolfgram (Cheverus football)
• 2008 Billy Goodman (Deering golf)
• 2007 Andy LeFebvre (Deering soccer)
• 2006 John Simpson (Cheverus cross country)
• 2005 Jim Ouellette (Cheverus golf)
• 2004 Mike Bailey (Portland football)



Carrie Earls/George Sherry – Waynflete soccer

Contributed photo

Contributed photoWaynflete’s girls’ soccer team entered the season hoping to compete. The Flyers wound up playing for a regional title. As a result, the program is now back at its accustomed level in the upper echelon.

Co-coaches Carrie Earls and George Sherry have made the Flyers relevant again and for their work, The Forecaster is naming them our Portland edition Fall Coach(es) of the Year, of a girls’ team.

Earls, who played soccer at Deering High School and St. Joseph’s College, and Sherry, who played at the University of Maine, took over the Waynflete program in 2018 and finished 4-10 and out of the playoff running. The Flyers got to the postseason the following year, but won just three times, then in 2020, had their season shortened by COVID. Signs of progress arrived in 2021, when Waynflete went 10-7 and got all the way to the Class C South semifinals, where it lost to Traip Academy.

This fall, the Flyers took it to another level. Waynflete started 4-0, enjoyed another four-game win streak later in the season and finished 10-4, its best mark since 2015. The Flyers then blanked Monmouth Academy and Traip Academy in the quarterfinals and semifinals respectively to reach the regional final for the first time in six seasons. Waynflete would lose to eventual state champion Maranacook, 2-0, but what a season it was.

“We were thrilled with how the team came together this season,” Earls said. “We lost our entire back line, including the goalie to graduation last year, so we were a little worried about the make-up of our defense, but we got huge contributions from two freshman and a sophomore, who settled into one of the best defensive lines in Class C. We recorded 10 shutouts, only letting up 19 goals. Our veterans took care of business in the midfield and up top. We’re excited to be returning most of our starting lineup and excited for the 8th grade class we have coming in.”


Indeed, Waynflete figures to be just as strong, if not even stronger in 2023.

With Carrie Earls and George Sherry, our Portland edition Fall girls’ team Coach(es) of the Year, leading the way, it’s only a matter of time before the Flyers reach the pinnacle again.

Prior winners:

• 2021 Theresa Hendrix (field hockey)
* 2020 Craig Roberts (Cheverus soccer)
• 2019 Curtis Chapin (Portland soccer)
• 2018 Amethyst Hersom (Deering field hockey)
• 2017 Larry Nichols (Deering volleyball)
• 2016 Craig Roberts (Cheverus soccer)
• 2015 Amy Ashley (Cheverus field hockey)
• 2014 Arthur Mosen (Portland soccer)
• 2013 Todd Dominski (Waynflete soccer)
• 2012 Todd Dominski (Waynflete soccer)
• 2011 Beth Arsenault (Portland field hockey)
• 2010 Noelle Surette (Waynflete field hockey)
• 2009 Amy McMullin (Cheverus field hockey)
• 2008 Ziggy Gillespie (Waynflete cross country)
• 2007 Patsy Fowler (Cheverus field hockey)
• 2006 Dave Levasseur (Portland soccer)
• 2005 Tim Donovan (McAuley cross country)
• 2004 Jon Shardlow (Waynflete soccer)

Sports Editor Michael Hoffer can be reached at [email protected] Follow him on Twitter: @foresports.

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