Maddie’s Sail Loft hoists historic Marblehead Softball trophy

In 1939, Percy L. Martin, supervisor of the local Works Progress Administration for recreational projects, scheduled an exhibition softball game in Marblehead between General Electric and a high-grade team. The exhibition was scheduled to gauge interest by residents while the WPA considered investing in the creation of a softball league.​ Interest in the exhibition was high, and as a result additional games were played throughout that summer of 1939​, marking the inception of the Marblehead Softball League.

In the years that followed, the YMCA would take on the responsibility of organizing the league, inviting local fraternal and social organizations to participate. Marblehead’s police, fire and highway departments, town officials, the post office, Osbourne’s, Clippers, General Grants and Market Square all fielded teams. ​Lists of the Marblehead Softball League’s teams read like a chain of local businesses and establishments of today and yesteryear.

Fast forward 85 years, and the Marblehead Softball League has about 120 men playing each summer on eight teams and claims to be the “longest standing adult softball league in the world.” The league’s long history also boasts the involvement of a single team playing for 50 seasons, spin-off Sunday leagues, softball weekends, charity tournaments, dynasties (and perennial losers), fierce rivalries, travel all-star teams, fast-pitch and metal-bat eras, countless legacy players and many on-field parent-child combinations.

​The regular season starts in May and ends in August with all of the 2023 participating teams seeded for the playoffs.

This year’s playoff seeds were as follows:

  1. Breaking Balls
  2. Maddie’s
  3. SWI Sox
  4. Epstein Masonry’s Rockheads
  5. Kappy’s Liquors
  6. Casale Law Office’s Esquires
  7. Sidelines
  8. Cannabis Kove Dispensary 

Round 1 play-in games

  • Kappy’s Liquors defeated Cove in a mercy fashion.
  • Down by two runs entering the bottom of the seventh, Sidelines put runners on first and third with no outs but only scored once, so the Esquires squeezed out a 18-17 win to advance.
  • In Round 2, the Esquires narrowly escaped slaughter but couldn’t get the bats going and lost to the SWI Sox, 14-3.

Round 2 play-in games

The SWI Sox rolled through the Esquires, and the Rockheads ran around Kappy’s to move to the semifinals. 

Best-of-three semifinals

  • Riddled with injury, the SWI Sox and were put away by Maddie’s in two games.
  • The Rockheads never got the bats going and were ​quickly ousted by Breaking Balls in 2 games. 

​Best-of-three finals

Chad Osbourne of Maddie’s utilized all of the tips he learned about pitching from the late Reggie Hartley to shut down Breaking Balls, 10-7 in Game 1 and 10-1 in Game 2.

Members of the Maddie’s team celebrate the two-game sweep of top-seeded Breaking Balls in the finals, which allowed them to claim the 2023 Marblehead Softball League championship. The same squad won seven consecutive championships from 2012 to 2018 while sponsored by the Gerry 5. COURTESY PHOTO

Prior to gaining sponsorship from Maddie’s Sail Loft the team won seven consecutive seasons — 2012 through 2018 — while sponsored by the Gerry 5.

And yes, Chad is of direct lineage to the Osbourne’s team from the 1940s and Osbourne’s Petunias from the 1970s. 

Numbers retired

In June, the League gathered to retire the numbers of league-mates Reggie Hartley (12) and Jeff Scogland (44) who each passed away in the summer of 2022. The numbers were permanently installed on the shed at Green Street.

Hartley was 80 years old when he retired from playing in 2021 and had played in the league for 65 years. He was recently the pitcher for the Gerry 5 teams that had won seven straight championships.

Scogland played on the SWI Sox for 20 years, and his great play was only overshadowed by being the nicest guy in the league and everyone’s favorite opponent. There wasn’t a dry eye in attendance that evening.

Annual awards banquet

The Marblehead Softball League will host its annual awards banquet at the Gerry 5 on Thursday, Oct. 19 at 7 p.m. The banquet is open to all current and past players, and we would love to have you come down and share some stories from your days playing at Green Street.

If you want to keep up with the Marblehead Softball League, you can join our Facebook group by searching “Green Street Softball.” If you would like to attend the banquet, please RSVP to

Michael McCarthy has played in the Marblehead Softball League for 20 years and currently manages and serves as a utility player for Epstein Masonry’s Rockheads, which was formerly sponsored by Three Cod Tavern and Edward Jones. In response to the Current’s inquiry, he states that Peter Jaffe is the league commissioner and jokes that he serves the league as its “historian, unofficial general manager and head of the players’ association.”

Michael McCarthy
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