Taylor Canfield: On the climb to the Cup

Published on April 25th, 2018

By winning the 2018 Congressional Cup, Taylor Canfield joins sailing legends Gavin Brady, Peter Holmberg, and Rod Davis as the only four-time winner of this match racing crown. From St Thomas in the US Virgin Islands to Boston College, this 29 year old is now establishing himself in the realm of professional sailing.

Scuttlebutt editor Craig Leweck checks in with Canfield for an update.


When you graduated from college in 2011, match racing was your diving board into professional sailing. How does it fit in now?

Still quite strong as it has always been my goal to compete in the America’s Cup. When I was a kid, I was fortunate to see Peter Holmberg, who grew up in the Virgin Islands, get to the high point of the sport. I watched him succeed in match racing, and I was inspired do it the same as he did and, hopefully, have some of the same opportunities.

So I went all in on match racing, and when the America’s Cup took a turn into catamarans, it was time to try to figure out how to stay ahead of the curve while continuing my upward climb. I was able to skipper the M32 Class catamaran in Miami and in its Scandinavian series. This continued when the World Match Racing Tour shifted to catamarans.

Back in the day, the World Match Racing Tour was a big feeder into the America’s Cup, and once the switch to catamarans happened, it lost that connection, so the shift to the catamarans on the Tour was an awesome opportunity to stay in sync with the Cup.

But that was 2016 and 2017, and at the moment things are changing again, and to be honest, I’m not sure what the direction of the Tour will be for the future. With only three events announced in 2018, the Tour hasn’t shown us much to look forward to.

It’s difficult in two senses. One, there’s been quite a big cut in prize money, and two, the seemingly unorganized nature of the Tour at the moment makes it very difficult for us to plan. With less money and less events, we need to get sponsorship which is hard without an organized event schedule. As this is how we are deriving our income, we must also be pursuing other pro sailing opportunities outside the Tour. So these are challenging times.

Thank goodness for the Congressional Cup…

Absolutely. The Congressional Cup has always been one of the biggest match race events in the world, and I think it’ll always continue to be. It doesn’t use the most high-performance, up-to-date boats, and doesn’t have the biggest prize payout, but it’s an awesome event that was once part of the World Match Racing Tour but now stands strong on its own.

It continues to attract the top match racers in the world, so for us it’s very appealing. It’s here in the US, so we consider it a home event, but our commitment is bigger than that. It’s about the community out in Long Beach and how they put out such an amazing event. It’s a lot of fun for us to go and do.

So even though the prize money isn’t enormous compared to other opportunities, we’re able to put a really good team together this year and go sail. I think this was my eighth Congressional Cup in a row, so I’m happy to be a part of it and look forward to being a part of it for years to come.

Canfield and his winning Cup team.

Speaking of your crew, it looked like a garage band of all-stars that could all jam but hadn’t necessarily played together.

Yes, it definitely was a different crew this year, kind of a pickup crew given the uncertainty now of the match race schedule. The goal was to bring in the best people we could find in the US, but it required some shuffling when my long-time teammate Hayden Goodrick broke his foot.

But we gathered an incredible group of talent, and while not many of them had done not much match racing, we thought we could overcome that by sailing the boat better than the other teams.

With the long-event format, we were able to get everything put together and really work well as a team to become not only the fastest boat at the event, but by the Finals, the best match racing team at the event. It worked.

Were you inspired by this approach?

Absolutely. Individually, each member of the team has been active and successful. Nearly all of us had come straight from Charleston Race Week, so it was a tight turnaround, but we had two days of rest and then right back into racing, it’s just part of the routine.

Everyone was pretty fresh and really good at sailing. Also, Dan Morris had been in Long Beach for the past two weekends before Congressional Cup, sailing the Catalina 37s in two match race events. That was a huge help and a big gain for us.

With your America’s Cup aspirations, it had to feel pretty good beating in the Finals the American Magic team that has challenged for the Cup.

It always feels amazing to win the Congressional Cup, and while we had to overcome the full field, beating such a great team with the likes of Dean Barker and Terry Hutchinson made it that much sweeter for us.

I’m hearing rumors that your aspirations to get involved in the America’s Cup might be coming sooner than later.

There’s nothing to share at the moment but I’m continuing to look at options to join a syndicate. Hopefully there’ll be some good news to share in the near future.

So in the meantime, you stay fresh.

Indeed. We’ll be at the 2018 Bermuda Gold Cup next month (May 7-12), which is a historic match race event that’ll be sailed in IODs. I am still putting a team together at the moment, but I’ll 100% be there.

Like the Congressional Cup, the Gold Cup was once associated with the World Match Racing Tour but is such an awesome event that it stands strong by itself. It’s super appealing which helps attract the top match racing sailors.

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