Triple Crown of Charity Sailing Trophy 2025 winner announced
by CRAB Sailing 1 Nov 2025 09:02 AEDT
30 October 2025
Triple Crown of Charity Sailing Trophy 2025 © CRAB Sailing
The highly anticipated 2025 Triple Crown of Charity Sailing Trophy presentation and reception was held at the Chesapeake Region Accessible Boating Annapolis Adaptive Boating Center on October 30th. The leadership of Maryland Cures Cancer Regatta, the CRAB Cup, Hospice Cup, and Weems & Plath were present to celebrate the awarding of the trophy to Roger Mason and Chris Valentino for their record-breaking race and fundraising results as the Tradecraft Team.
The three Annapolis charity races attracted 238 boats, over 1,000 skippers and crew, and most importantly raised $556,627 for charity. The Triple Crown of Charity Sailing Trophy is awarded to the skipper with a combination of the lowest race scores and highest fundraising. All three races are scored individually and the results tabulated for the eventual champion.
The Trademark Team finished with the lowest number of points with two second place finishes and one first-place finish while raising $56,690. This year's champions Roger Mason and Chris Valentino also raised the highest amount of funds last year and they were recognized and awarded the Weems & Plath Rainmaker Award.
After receiving the trophy, Roger Mason's remarks focused on the importance of the Triple Crown's goal to increase participation in the three races and fundraising for their critical missions. Roger said the competition for the prestigious trophy was helping to build a community of service inside a community of sailors. He noted his personal connection to the charities and that his team of government (3-letter agency) retirees provided the name of their profession to create the name "Tradecraft" for the boat and team. The secret is out.
The team coming in second was J-22 Committed, sailed by Tracey and Warren Richter. The third-place finisher was John Heintz on his Harbor 20 Team Endurance. Both of them have won the Triple Crown Trophy in the past. The reception also was joined by past winners John Dodge and Dan Flagler making it an evening filled with some of the most generous sailors on the bay.
Weems & Plath former owner Peter Trogden was also in attendance to share the story of the creation of the Triple Crown of Charity Sailing Trophy. The trophy is on permanent display at the CRAB Adaptive Boating Center.