Tight Race in Charity Sailing Triple Crown

The most successful skippers in Annapolis’s three charity sailing events competed all season for one special honor: the 2019 Triple Crown of Charity Sailing trophy. The winner was announced at Annapolis Market House this past week, and the race couldn’t have been much closer.

The executive director of Chesapeake Region Accessible Boating (CRAB), Paul “Bo” Bollinger, was inspired by his Kentucky roots to create the Triple Crown as a way to encourage participation in three charitable races: the Leukemia Cup, CRAB Cup, and Hospice Cup.

The Triple Crown trophy, now in its second year, goes to the sailor with the combined best finishes and highest fundraising totals in all three races.

The competition came down to just one point. Bollinger said Dan Flagler and John Heintz were the only two sailors who possessed the “stamina, wherewithal, and gumption” to qualify for the Crown by not only finishing in each of its races but, more importantly, raising funds for the respective charities that they benefit (Leukemia & Lymphoma Society, CRAB, and Chesapeake-area hospices).

When the race finishes and fundraising dollars were tallied, Flagler, a part-time fleet director for CRAB who competed in a Pearson 31 named Flagfest and was second in 2018, edged out 2018 winner Heintz, a leukemia survivor who sailed Endurance, a Harbor 20. 

Friendly competition is fun, but Flagler and Heintz couldn’t have cared less about who won the trophy, a 1920s, one-of-a-kind prize that once belonged to the Patapsco Sail Squadron and was nursed back to beauty by Peter Trogdon, co-creator of the Triple Crown and former president of race sponsor Weems & Plath.

In his acceptance speech, Flagler said, “Everyone has connections to these causes, but not everyone knows what they can do to make things better. The Triple Crown is a great way to do so, encouraging you to make a very real commitment to not only raise money but also work your way through all three races. I hope there will be at least ten of us up for the trophy next year, and at least twenty the year after that!”

Flagler credits his brother with spearheading the team’s jump from 15 CRAB Cup benefactors in 2018 to 53 this year.

Heintz, who received a bone marrow transplant from his son, Eric, following his Acute Myeloid Leukemia diagnosis, agrees with Flagler that the cause is more important than the win:  

“I feel great [with my second place finish] because, while only two of us qualified, it still means that more people were out there participating in three great races and supporting three great organizations and causes,” said Heintz. 

The leaders of the three charities all deemed the second Triple Crown – and its impact on their individual causes – a resounding success. 

In its 26th year, the Leukemia Cup Regatta drew nearly one-hundred boats across fourteen classes, raising a total of $225,000 for the Leukemia & Lymphoma Society, Maryland Chapter, and the research, patient programs, and advocacy to cure blood cancers that it supports.

The CRAB Cup, in its 12th year, saw 75 participants raise over $110,000 for the non-profit that provides specially-adapted sailboats for those with disabilities, recovering warriors, and children from at-risk communities.

The 38-year-old Hospice Cup raised approximately $100,000 to help increase awareness of hospice care and directly support hospice programs around the region.

-Steve Adams