Q&A with Taylor Canfield, winner of the Chicago Match Cup race

By Dana Getz

Tall Ships Chicago returned to Navy Pier August 7-11, partnering with the Chicago Match Cup for the first time ever. Twelve teams from seven nations sailed alongside 14 majestic Tall Ships as they competed for $100,000 in the only U.S. stop on the six-city Alpari World Match Racing Tour.

The four-day affair kicked off with the inaugural Tall Ships parade and round-robin racing, in which teams faced off on windward-leeward courses. After a challenging few days, the USOne sailing team took home their third consecutive win, led by skipper Taylor Canfield and his crew of Rod Dawson, Mike Rehe and Hayden Goodrick. Canfield’s spinnaker tore at the first mark rounding during the third race, leaving him vulnerable to opponent Keith Swinton and the Black Swan Racing Team. With the big downwind sail increasingly descending, trimmer Mike Rehe was able to hold things together while Canfield maintained his lead to the finish. During the fourth race, Canfield caught Swinton with a bold but risky maneuver, resulting in a collision and penalty for the Black Swan Racing team. Tied at 2-2, the win could have gone either way, but Canfield’s early lead led to a clean finish in the final match. The victory earned Canfield and his crew a $25,000 grand prize, boosting them to within nine points of tour leader Ian Williams, the number one ranked match racer in the world.

The win was especially significant for Canfield, who moved to Chicago three years ago to work as a sailing director for the Chicago Match Race Center. At 24-years-old, he is the youngest skipper on the tour. He grew up sailing in his home of St. Thomas in the U.S. Virgin Islands, securing his spot as a first-time tour card holder after winning both the Monsoon Cup and Argo Group Gold Cup last year.  In the days following his exciting victory, we chatted with Canfield on the challenges of being a newcomer, his mindset during the race and what he loves most about living in Chicago.


This is your first year as a Tour Card Holder on the Alpari World Match Racing Tour. Tell me a little bit about your journey to get here.

I have been match racing for about seven years now and have always had my eye set on becoming a tour card holder. While we have been slowly climbing the rankings the past years, it was not until last year when I locked in a solid crew that we really started to turn it up. Hayden Goodrick, Mike Rehe, Rod Dawson and Dan Morris joined me in 2012 to win two of the eight WMRT events as wild card holders. This was when we realized we had what it takes to compete at the level of the top match racers in the world.


You’re also one of the youngest skippers on the tour. Do you think you’re viewed as an underdog?

There is definitely some extra pressure as the youngest skipper on the tour, although I do not think we are viewed as the underdog after winning the two events last year. We are definitely looking to continue to prove ourselves throughout the rest of our first season.


What are the biggest challenges you will face? Do you feel you have any advantages?

One of our biggest challenges is actually paying for all of the events. While some big wins have covered some of the events, the prize money is not always guaranteed. Our biggest advantage is having Chicago Match Race Center to train at during the year if we feel necessary.


How did it feel to win the Chicago Match Cup?

Winning Chicago Match Cup was unbelievable. Not only was winning after being 0-2 in the finals a great feat, winning an event in my new hometown with all the support made everything that much better. It was great having all of our family and friends there to cheer us on.


Tell me about your experience during the race. What was going through your head? Did you think it was over when you tore your spinnaker in the third race?

I would be lying if I said I was not a little nervous, although what did we have to lose with three must win races to go? We knew we were sailing the boat well, yet we still had to put together a good start and well-sailed tactical race. I was thinking that no matter what happened after race three, second place was still a respectable finish. As we rounded the top mark and saw the rip in the kite, I actually thought it was going to affect us more than it did. After rounding the leeward mark still ahead, I did not have any doubt in my mind we could still easily win the race.


Who was your toughest competition?

Toughest competition was definitely Keith Swinton and his Black Swan Racing. We knew going into this event that Swinton is really good in the type of boats we were sailing: TOM 28. He and his team had a huge comeback after starting off the regatta slow. They really switched it on after making it to the quarterfinals where they beat Adam Minoprio 2-0, and then followed it up by beating Williams 2-0 in the semi-finals.


You’ve traveled all over the world. Do you have a favorite place to sail?

Favorite place to sail is definitely St. Thomas, my hometown. Beautiful weather, crystal clear water, and 15-25 knots almost every day.


What’s special about sailing in Chicago?

Chicago is a great place to sail because you can get any conditions you can imagine—big breeze from the north with big waves to light shifty conditions from the west with flat water. It allows you to prepare for any venue by offering the best conditions at times and some of the most challenging conditions at other times.


Why do you think it was chosen as the only U.S. stop on the world tour?

Chicago was chosen as a stop on the AWMRT because of a few things. One: Chicago Match Race Center. Founded by avid Match Racer Don Wilson, CMRC has been running international match race events for six years now. Two: stadium sailing at Navy Pier. You could not ask for a better viewing area.


What do you like to do in Chicago when you’re not sailing?

I like to explore the city. There are so many areas with new exciting buildings and restaurants. I also like to be outdoors: running down the lakefront trail, walking through the zoo, being out on the lake. Best skyline I have ever seen.


Lastly, what advice do you have for young sailors hoping to join the tour someday?

Work hard and stay relaxed and anything you want bad enough will be much easier to achieve. Also, be sure to find the right people to sail with because you will be spending a lot of time with them. It’s not only the chemistry you have while you are sailing, but the relationship you have with them on land will really separate the good from the best.