The 2025 Triple Crown of Charity Sailing Trophy has been awarded to the Tradecraft Team, led by Roger Mason and Chris Valentino, after a record-setting season of racing and fundraising that showcased both competition and generosity on the Chesapeake Bay.
Tradecraft Team Takes 2025 Triple Crown Title
The trophy presentation and reception were held October 30 at the Chesapeake Region Accessible Boating (CRAB) Adaptive Boating Center in Annapolis. Leaders from the three participating charity regattas—Maryland Cures Cancer Regatta, the CRAB Cup, and Hospice Cup—joined sponsor Weems & Plath to recognize this year’s champions.
Mason and Valentino’s Tradecraft Team claimed the 2025 Triple Crown of Charity Sailing Trophy with the lowest combined race score across all three events, posting two second-place finishes and one first-place finish. Just as importantly, they topped the fundraising leaderboard by bringing in $56,690 for the beneficiary charities.
The team was also honored with the Weems & Plath Rainmaker Award for raising the highest amount of funds last year, underscoring their consistent commitment to the cause.
Record Fundraising for Annapolis Charity Regattas
In 2025, the three Annapolis charity races collectively attracted 238 boats and more than 1,000 skippers and crew. Together, they raised $556,627 for local causes, including cancer research, adaptive boating, and hospice care.
Organizers say the Triple Crown format is helping drive both participation and donations, turning what might be three standalone regattas into a unified season-long challenge for sailors who want to give back.
How the Triple Crown of Charity Sailing Works
The Triple Crown of Charity Sailing Trophy is awarded based on a combination of on-the-water performance and fundraising. Each skipper’s results in the Maryland Cures Cancer Regatta, CRAB Cup, and Hospice Cup are scored individually, then tabulated to determine an overall champion.
The system rewards both consistent racing results and sustained fundraising leadership. In 2025, Tradecraft’s blend of podium finishes and top-tier fundraising put Mason and Valentino at the front of the pack.
Mason: Building “A Community of Service” Among Sailors
After receiving the trophy, Mason focused his remarks on the broader purpose of the series and the impact of the sailors who participate.
He emphasized that the Triple Crown’s goal is to boost both race participation and charitable giving, saying the competition is helping to build a “community of service” within the local sailing community. Mason also shared his personal connection to the beneficiary charities and noted that the team name “Tradecraft” came from the profession of his crew, many of whom are retirees from three-letter government agencies. “The secret is out,” he added.
Top Finishers and Past Champions Recognized
The Triple Crown standings were tight at the top. J/22 Committed, sailed by Tracey and Warren Richter, finished second overall. Third place went to Harbor 20 Team Endurance, skippered by John Heintz. Both boats are past Triple Crown champions and remain regular supporters of Annapolis’ major charity regattas.
The reception drew several previous winners, including John Dodge and Dan Flagler, making the evening a reunion of some of the most active and generous sailors on the bay.
Trophy on Permanent Display at CRAB Adaptive Boating Center
Former Weems & Plath owner Peter Trogdon attended the event to share the story behind the creation of the Triple Crown of Charity Sailing Trophy. The award is on permanent display at the CRAB Adaptive Boating Center, serving as a year-round reminder of the partnership between sailors, sponsors, and nonprofits.
With more than half a million dollars raised in 2025 and another deserving champion crowned, organizers say the Triple Crown of Charity Sailing series continues to grow as one of Annapolis’ signature ways to combine competitive sailing with community impact.
