Berkshire Black Bears

Lore & Background

At the end of the 2003 season, the Berkshire Black Bears did not renew their lease. Owner Jonathan Fleisig moved the team to New Haven, Connecticut, where it became the New Haven County Cutters.

Reader's Guide

The Berkshire Black Bears represent a brief, unsuccessful chapter in independent minor league baseball. Their two-year existence in Pittsfield, Massachusetts, was defined by consistently poor on-field performance—finishing last or near-last in their division and league—and low attendance that worsened from the first season to the second. Despite managerial and coaching changes after 2002, the team's 2003 record improved only to second-worst in the league. The franchise's relocation to New Haven, Connecticut, and rebranding as the New Haven County Cutters underscores the instability common in independent baseball, where financial and competitive struggles often force moves. The Black Bears' legacy is primarily as a short-lived team that failed to gain a foothold in its community, serving as a cautionary example of the challenges faced by low-revenue independent clubs.

Did You Know?

• The Berkshire Black Bears tied the Allentown Ambassadors for the worst first-half record in 2002 at 14–31.
• Their 10–34 second-half record in 2002 was the worst in the entire Northeast League.
• Manager George Scott was replaced by Darren Bush for the 2003 season.
• The team's attendance dropped from 56,295 in 2002 to 43,846 in 2003.

Origins & Home

The Berkshire Black Bears first took the field in 2002 as a minor league baseball franchise competing within the independent Northeast League. Their home ground was Wahconah Park in Pittsfield, Massachusetts, situating the team firmly in the western reaches of the state. As an independent league club, the Black Bears existed outside the conventional farm-system hierarchy that governed much of organized baseball, carving out their own niche in the broader professional landscape. The franchise represented a meaningful opportunity for Berkshire County to host competitive baseball at a professional level, offering local fans a regular-season anchor and a community gathering point around the diamond. Though their time in Pittsfield would ultimately span only two seasons, the 2002 debut marked the opening chapter of a brief but notable story that would eventually carry the franchise across state lines into Connecticut, where it would be reborn under an entirely new identity.

On-Field Struggles

The Black Bears' inaugural 2002 campaign in the North Division was defined by consistent struggle. In the first half of the season, they finished last with a 14-31 record, a mark they shared with the Allentown Ambassadors for the worst showing in that stretch. The second half brought no relief: the team again placed last in their division at 10-34, a record that also represented the worst in the entire league for that period. Beyond the scoreboard, the fan base struggled to materialize. Across 43 home games, the Black Bears drew 56,295 total fans, averaging just 1,309 per game — figures that placed them near the bottom of the league in both categories. The combination of on-field futility and thin crowds painted a picture of a franchise still searching for its footing in a competitive independent circuit.

The 2003 Rebuild

Following the disappointing 2002 season, the Black Bears made significant front-office changes heading into 2003. Manager George Scott was let go, and the organization announced Darren Bush as his replacement for the upcoming campaign. The club also brought in Jim Dedrick to serve as pitching coach, signaling a desire to shore up the mound. The results showed modest progress: the team improved to a 41-51 record, a clear step up from the previous year. However, in the context of the full league, that mark still placed them as the second-worst team, underscoring how deep the competitive gap remained. Attendance told a similar story, dipping to 43,846 fans for an average of just 946 per game — again measuring poorly against league peers. The 2003 season thus represented a partial recovery that nonetheless left the franchise far from competitive stability.

Relocation & Aftermath

At the close of the 2003 season, the Berkshire Black Bears made the decision not to renew their lease at Wahconah Park, effectively ending the franchise's two-year run in Pittsfield. The team's owner, Jonathan Fleisig, who remained committed to pursuing a career in independent baseball, chose to relocate the franchise to New Haven, Connecticut. There, the club was rebranded as the New Haven County Cutters, shedding the Berkshire identity entirely and starting fresh in a new market. The transition marked the final chapter of the Black Bears' brief existence in Massachusetts. What had begun as a local independent baseball venture in the Berkshires ultimately became a Connecticut enterprise, carrying forward the organizational structure while leaving behind the name, the park, and the community that had supported the team through its two seasons of struggle.

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