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Masconomet soccer coach Len Emmons looks past “living legend” status. By Sarah A. Ditkoff. Photograph by Robert Boyd.

With high school sports underway, our attention gets turned once again to a regular schedule of matchups. Typically, it’s the kids we cheer for, but this season, a few North Shore coaches are on the cusp of some major milestones.

Search the Internet for Len Emmons of Masconomet Regional High School in Boxford and odds are good that many of the articles recapping his soccer matches refer to him as a “living legend.”

“I can list wins and losses, but I try to live in the now,” Emmons says. “What’s most gratifying to me is to see the relationships develop between the players that I know are going to last a lifetime.” His boys’ varsity team won the state title in 2008, not to mention the Cape Ann League (CAL) Large title, the MIAA Division 2 North title, and the Division 2 Eastern Massachusetts title.

With 546 wins under his belt, he’s only the third boys’ soccer coach in the Commonwealth’s history to reach 500 wins in his career. When asked about this milestone, Emmons downplays it. “It’s all about longevity,” he says. “You have to have cooperative parents and talented players. I don’t want to be the center of attention. It’s all about them.”

During his time as head coach at Masconomet (he’s been there since 1972), Emmons has racked up 27 CAL titles and four North Division Champion titles. “I’ve enjoyed the game and every year is different,” says Emmons, who is now 65 years old. “My only regret is that I can’t keep up with some of these boys anymore. We’re Division 1 this year, and I’m excited to go out and show these teams what we can do.”

The Watch List

Three more coaches to keep an eye on this season.

2 coaches1. St. John’s Prep golf coach Larry O’Neill has spent his 20 cumulative seasons at the Danvers school amassing a 284-21-7 record. At one point, his team celebrated a 116-game winning streak. Under his leadership, teams have nabbed 16 league titles, 13 Division 1 North titles, and five state championships. “Anytime you win anything, it’s an achievement,” he says, “but the three consecutive state titles we won in ’87, ’88, and ’89 were close to the top.”

coach walking field2. Field hockey coach Donna Andersen enters her 16th season at Triton Regional High School in Byfield this year. “This year, they’re a determined group, and they’re doing things they never thought they’d do.” It’s been four years since Andersen was named Cape Ann League Coach of the Year, but she keeps busy, balancing field hockey with coaching the school’s multi-title-winning boys’ lacrosse team and taking over as athletic director.

football coach talking to players

3. These next few seasons will be full of anticipation for Steve Hayden of Pentucket Regional High School. He has bragging rights to 177 wins over his 28 years as varsity football coach, and with the promise of a 200-win milestone on the horizon, Hayden is playing it cool. “A perfect season for me would be for all my kids to come out perfectly healthy,” he says. “It’s a healthy experience to compete in the right way.