Taylor Canfield: From sailing’s boxing ring to SailGP starting king

What does it take to drag a SailGP team off the bottom of the standings and into genuine contention? Taylor Canfield.

Canfield has worn a lot of hats during his time on the water, but his path into the driving seat of sailing’s newest groundbreaking league is a winding one. Paved with silverware, near-misses and the odd dose of heartbreak, Taylor and his US SailGP team are now a top-notch outfit.

The Boston College graduate first earned his stripes in the realm of match racing, sailing’s equivalent of a boxing match, one vs one, using the racing rules to deal the blows. He won the World Match Racing Tour (WMRT) in 2013, as well as in 2020, with close friend and professional sailor Mike Buckley on his team. Buckley is now CEO of the US SailGP Team.

Since its inception in 2000, the American is one of four multi-time winners of the WMRT, alongside fellow SailGP driver Phil Robertson. Whilst competing on the tour regularly, Canfield also climbed the ranks of the illustrious Congressional Cup.

The America’s Cup is sailing’s pinnacle match racing event - arguably, sailing’s pinnacle event full stop - but the Congressional Cup is the next best thing. The event has fed multiple America’s Cup skippers, including Dean Barker, Terry Hutchinson and Dennis Connor.

The annual event takes place in Long Beach, Los Angeles, each year and culminates in the presentation of the Crimson Blazer. Taylor has slipped the winning jacket on five times: in 2014, 2015, 2016, 2018 and 2021, amounting to winnings that are said to total over $85,000 USD. He sits equally alongside Ian Williams, both with a total of five Crimson Blazers.

Following his penultimate Congressional Cup victory, Canfield turned his attention to The America’s Cup itself. Alongside Buckley, the pair announced an entry to the 36th America’s Cup, with the Long Beach Yacht Club, under the title of Stars & Stripes Team USA. A touching callback to Dennis Connor’s all-American 'Stars & Stripes' Cup campaigns for the United States.

Unfortunately, the entry fell through, and the team failed to pay an entry fee in time for the first America's Cup World Series Regatta in Cagliari, Sardinia. An event that never actually went ahead. A disappointing outcome that the global COVID-19 pandemic certainly wouldn’t have helped with.

As the match racer’s America’s Cup hopes were ongoing during that period, Canfield was also involved in SailGP. The U.S. Virgin Islands-born sailor stepped into the US SailGP Team in season one as flight controller before playing a part with the Spanish outfit in season two in the same role.

Following the sale of the US SailGP Team at the end of 2023 to founding Uber engineer Ryan McKillen, his wife Margaret McKillen and Mike Buckley, Buckley emerged as the team’s CEO with Canfield in the driver’s seat. A move that brought the two friends together again, this time on a new venture.

Taylor took over driving responsibilities from Jimmy Spithill mid-way through season four and went on to have a shaky and disappointing season five. The team finished in last place, and many questioned the new direction of the team and whether they had what it takes to win.

That difficulty wasn’t without a wallop either. Canfield had a notable port-starboard incident with the British team in Sassnitz, 2025. As the kept-clear boat, the incident put the US team out of the following day’s racing after they had to donate a section of their hull to the British for repairs.

Fast forward to season six, and the US team turned it all around. Despite being deemed at fault for another major pile-up in New York, the US team are serious contenders that fight for podium positions on the regular. 

That kind of ability in the midst of adversity requires a fierce and unrelenting sailing style. Canfield is all about getting the reps in; he frequently references his team's process-oriented approach, a value that he underpins himself.

Aside from his SailGP duties, Taylor regularly competes on the M32 catamaran circuit for Surge, another one of Ryan McKillen’s ventures; it’s a role that has certainly helped to forge him into a formidable threat on the SailGP start line.

From the corner of the match racing ring to a frontrunner in the driving seat of SailGP, Canfield's journey has been anything but linear. All of Taylor’s experience has shaped him into a ruthless operator who leaves no stone unturned.

With Buckley alongside him and the McKillens behind him, Taylor has the platform his talent has long deserved. The Crimson Blazers proved he could win; now he has the chance to prove he can do it in SailGP.

On current form, you'd be brave to bet against him.