Team Tradecraft Claims 2026 Weems & Plath Triple Crown
The Annapolis trophy honors the skipper with the best mix of racing results and charitable fundraising across three regattas.
Updated on Nov. 11, 2026 in Philanthropy
Team Tradecraft, led by Roger Mason and Chris Valentino, claimed the 2026 Weems & Plath Triple Crown of Charity Sailing Trophy, which was presented October 22 at the CRAB Adaptive Boating Center in Annapolis. Three Annapolis charity regattas drew 215 boats and more than 1,000 sailors and raised $604,000 for local charities.
Why it matters
The Triple Crown rewards both racing performance and fundraising, linking competitive sailing to support for Annapolis-area charities. The results highlight how regatta participation can translate into measurable local giving.
The three regattas raised $604,000 from 215 boats and more than 1,000 sailors, with Team Tradecraft contributing more than $56,000 on its own. The extraction does not break down how funds were allocated among the beneficiary charities.
The players
Team Tradecraft
A sailing team skippered by Roger Mason and Chris Valentino that competes in Annapolis charity regattas and has a strong fundraising record.
Eastport Yacht Club
An Annapolis-area yacht club that co-hosted the race committee for the charity races.
The details
Each regatta was scored separately, and the combined results determined the overall champion. Team Tradecraft recorded one sixth-place finish and two second-place finishes, while Warren and Tracey Richter, sailing the J/22 Committed, finished second overall and John Heintz, aboard the Harbour 20 Endurance, placed third.
Timeline
2025: Mason and Valentino earned the Weems & Plath Rainmaker Award for raising the most money of any team.
2026 season: Three Annapolis charity regattas were held, raising $604,000.
October 22, 2026: The Triple Crown trophy was presented at the CRAB Adaptive Boating Center.
Market Landscape
The Triple Crown combines competitive racing with fundraising in a single scoring system, a model that ties sailing performance directly to charitable giving across Annapolis. The 2026 results show that multi-regatta charity series can channel more than $600,000 into local causes in a single season.
Annapolis-area sailors and sponsors can see how regatta participation translates into measurable support for local charities. Residents interested in similar events can look to the Triple Crown structure as a model for combining competition with giving.
The takeaway
Combining competitive sailing with fundraising can channel substantial support to local charities, as the $604,000 raised across three Annapolis regattas demonstrates. Participants and supporters can use the Triple Crown model to structure their own charity events.
Further reading
For more on local giving efforts, explore Annapolis Philanthropy coverage.
Source note: This article includes information reported by Eye On Annapolis.
