Midwinters Roundup: SYC RegattaPRO Midwinters
From November through February, five of San Francisco Bay’s biggest one-design fleets tuned up in the “offseason” for the upcoming racing season. Across the five fleets (J/105, Express 27, J/88, J/24 and Moore 24), 52 boats competed in at least one of the scheduled four days of racing, with one race day each month from November through February.
Across all of the fleets, eight races were sailed in the series (two per day of racing), with each boat afforded two drops for the series.
J/105 Fleet
The biggest one-design fleet on the Bay was also the biggest one-design fleet in the series, with 20 boats registered, and 19 boats competing in at least two days of racing. The series was won by William Woodruff’s Roulette (SBYC) with a net total of 16 points.
After starting off the series in November with sixth- and a fourth-place finish on day one of the event, Woodruff and co. won both December races and the first January race to catapult themselves up the standings. Roulette would end up dropping an 11th (race six) and a seventh (race 8), and finished third in race seven to secure the series win.
Seven points behind Woodruff in second was Walter Sanford’s Alchemy (SFYC) with a net total of 23. Alchemy started somewhat slowly, recording a ninth and a 16th in races one and three respectively (with a second sandwiched in between the less desirable results), which would become their two drops for the event. Alchemy then found her consistency in the final five races of the event, finishing fourth in races four, five and seven, and adding on a third and a sixth in races six and eight.
Rounding out the podium was Arbitrage (StFYC), driven by five-time US Women’s Match Racing national champion Nicole Breault. With both of their drops eaten up by their not competing in the first weekend of racing and therefore receiving two DNCs, Arbitrage finished outside of the top five only twice in the final six races of the event for a net total of 27 points.
Interestingly enough, neither Alchemy nor Arbitrage, the second- and third-place boats in the regatta, won a race. As mentioned above, Roulette won three. Scott Sellers and Harrison Turner’s Beast of Burden (StFYC), who won races one and six, finished fourth in the series, one point behind Arbitrage with a net total of 28. Tom Struttmann’s Arrived! (StFYC) won race two, and finished sixth for the series. Tim Russell’s Ne*Ne (SFYC) won the final two races of the series, and finished eighth overall.
Express 27 Fleet
The Express 27 fleet was the second-biggest fleet racing in the series, with all 16 registered boats racing at least two of the four days. A familiar face came out on top: the winners of the last three Express 27 national championships, Will Paxton and team on Motorcycle Irene (RYC). Paxton and co. finished with a net total of six points, winning all but one of the eight races. Their only non-bullet was a third-place finish in race two.
In second was Katie Cornetta’s Freaks on a Leash (RYC) with a net total of 19. Cornetta’s only non-top-three finish in the series (outside of two DNCs from the first day of racing, which would be her drops) was a TLE-7 in race seven. Rounding out the podium was a Tahoe Express team in Eric Villadsen and Ashley Farr’s New Wave (SLTWYC), also with a net total of 19. Cornetta’s two second-place finishes to Villadsen and Farr’s one proved to be the tiebreaker for second. The only non-Motorcycle Irene race winner was Rebecca Hinden and her team aboard Bombora (EYC), winners of race two.
J/88 Fleet
In the tightest class thus far in terms of the scores, Tom Thayer’s Speedwell won the six-boat J/88 fleet with a net total of 11 points. He and his team recorded five second-place finishes and one bullet across the series. Thayer and team never finished outside of the top three, dropping third-place finishes in races three and four.
In second place was Dave Corbin’s Butcher (SBYC) with 12 points. Corbin and co. won two races, but also had to keep two third-place finishes (with a third and a fourth being their drops), which gave the win to Speedwell. Brice Dunwoodie, whose Ravenette (StFYC) won the J/88 division at the 2025 Rolex Big Boat Series, won three of the six races that he competed in, but didn’t race the final day of the series.
J/24 Fleet
Jasper Van Vliet’s Evil Octopus (RYC) recorded a net total of eight points to top the six-boat J/24 class in dominant fashion. Van Vliet won four of the eight races, and finished outside of the top two only once (a fourth in race seven). Richard Stockdale’s Froglips (RYC) was in second place with a net total of 13 points.
Moore 24 Fleet
Of the seven Moore 24s registered, six raced in at least one race for the series. John Siegel’s Moorigami (StFYC) won with a net total of 11 points, edging out Conrad Holbrook’s Topper II (RYC) on tiebreaker. Siegel won three of eight races, while Holbrook won “only” one to claim the tiebreaker, even though Holbrook had a lower total score for the series (Siegel dropped two fourth-place finishes, while Holbrook never finished worse than third).