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Marblehead's 11U All-Star team is made up of Landon McKay, Kevin O’Leary, Charlie Demakes, Charlie Ainlay, Landon Coyne, Will Manning, Chet Whitten, Zach Weisman, Roy “Hobbs” Berman, Archie “Showtime” Wynn, Michael Brackman, Wylie Aamoth, Manager Patrick O’Leary, and coaches Eric Weisman, Jesse Ainlay, and Elias Demakes. (Elias Demakes)

A core of champions in Marblehead

Joey Barrett

June 30, 2025 by Joey Barrett

MARBLEHEAD — Sometimes, people throw out the word “dynasty” like it’s nothing – as if it’s not a top-tier recognition in the world of sports.

One championship: great.

Two: even better, but not quite a dynasty.

Three or four: now we’re talking.

Such is the case for Marblehead’s 11U All-Star team, made up of a core group that recently won its fourth consecutive Cal Ripken district title, spanning back to when players were 8 years old and winning the state championship.

Better yet, the team is undefeated in the district across the last four years.

“It’s the same core,” said Manager Patrick O’Leary, who has helmed that core all four years. “The team is a little bit different from year to year . . . but for the most part, it’s the same team.”

Marblehead completed its four-peat last week. It took down Winchester, 13-4, to top the district yet again.

But it wasn’t easy. The team trailed, 4-0, in the opening inning.

“Every game we’ve played, in the districts, we’ve been losing,” said O’Leary, joined by coaches Eric Weisman, Jesse Ainlay, and Elias Demakes.

After the early bump, Marblehead plated runs in every inning. (The third and fourth innings were when it broke the game open.)

O’Leary credited the kids – and, of course, defense.

“Players win games. Coaches can lose them, but players are the ones who win them,” he said. “It’s our defense, which is a team effort and they should be very proud.”

Wins are cherries on top, but O’Leary touched on a few life lessons that come with the sport.

“A lot of high-stress situations over the years . . . We have a lot of success, so we end up playing the best teams in the state frequently,” he said. “You’re not all going to be major leaguers, but you’re all going to be grown men some day. We try to teach them our philosophy: Regardless of what’s happening in the game, we try to put a championship effort on the field – every pitch, every play.”

Of the 12-player roster, each brings something different to the diamond.

Landon McKay is a gifted fielder, hitter, and baserunner, often setting the tone as a true leadoff man; Kevin O’Leary, a tenacious catcher, has caught every inning of every district and state tournament game the last four years; Charlie Demakes brings speed, power, and excellent fielding; Charlie Ainlay is the ace of the pitching core, while also being smooth with the glove; Landon Coyne is a power hitter who leads the team in home runs; Will Manning, a speedy power hitter, catches eyes with clutch performances; Chet Whitten hits for average and plays stellar defense at any position; Zach Weisman just might be the best center fielder in the tournament, according to his manager; Roy “Hobbs” Berman has an excellent bat, but is even better at second base; Archie “Showtime” Wynn leads the team in outfield assists every year; Michael Brackman throws fireballs, as said by Patrick O’Leary, and comes with a dependable bat; while Wylie Aamoth shows a maturity beyond his years with the bat and his glove.

“It’s a wonderful group of kids and they understand the idea of teamwork and pulling for each other,” Patrick O’Leary said. “It’s very impressive what they’ve been able to do.”

  • Joey Barrett

    Joey Barrett is the Daily Item's Sports Editor. He reports on local high schools, colleges, and professional teams. Prior to his current position, he worked for UMass Athletics, the Cape Cod Baseball League, and Gannett Media, among others. Barrett was also Sports Editor at Endicott College and treasurer of Endicott's Society of Professional Journalists branch.

    View all posts

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