Caleb Paine on winning a US Sailing Rolex Yachtsman of the Year Award

by David Schmidt, Sail-World USA Editor on 10 Mar 2017 On August 16, 2016 Caleb Paine (USA broke the longest-running medal ceremony dry spell for American-flagged Olympic sailors since the 1930s when he captured a bronze medal in the Finn class at the Rio 2016 Olympics. Needless to say, the American sailing world was thrilled for Paine and his proud international accomplishment. And at just 26 years young, Paine has the possibility of several more Olympic quadrennials in his future, which is certainly great news for American Olympic-sailing interests.

Given the magnitude of Paine’s bronze medal, and the fact that it represents the first medals that American sailors have collected since Anna Tunnicliffe and Zach Railey took home gold and silver (respectively) from the Beijing 2008 Olympics, it was deserved-but-not-surprising news the day that word broke that Paine won the coveted 2016 US Sailing Rolex Yachtsman of the Year Award.

What is a bit unusual, however, is the fact that Paine took a different lane out of high school than most of his peers, setting college and career on hold to pursue his Olympic dreams. While this strategy is much more aligned with the Olympic tracks of many international sailors, it represents the course less sailed when compared to the traditional American model of college sailing, followed by an Olympic campaign. (N.B., previous successful American Olympic sailors, perhaps most notably John Kostecki, have followed this same sailing-centric path en route to winning their Olympics medals.)

I caught up with Paine on the phone to talk about his proud US Sailing Rolex Yachtsman of the Year Award and his future sailing plans.

Do you remember how old you were when you first became aware of the US Sailing Rolex Yachtsman of the Year Awards?
Oh, I'd probably say it was around probably 12 or 13 years old. And as soon as I heard about it, I knew it was definitely one of the highest honors you could get in American sailing.

Do you remember some of the first athletes who were winning the awards when you started tuning-in to it?
Yeah, I knew JJ Fetter had won a [US Sailing Rolex Yachtswoman Award] several times and Mark Reynolds and you know, just a lot of the great Olympic athletes, especially from California, that I always idolized as a kid.

So was it a goal of yours to win one of these proud rewards, or do you see your new timepiece as more a trapping of your proud Bronze-medal win at the Rio 2016 Olympics?
I would say it was something I always have dreamed of, but it wasn't ever my true goal, but I have always known that winning a Rolex [Award] or being nominated as a Rolex Yachtsman of the Year is one of [our sport’s] highest honors.

More than anything, it's just a joy to have been awarded, just knowing the status that it has.

So what was your reaction when you heard that you won the award this year?
A shout of joy, that's for sure. I was just ecstatic-was such an honor.

Tell me about what is was like to stand on that stage in New York and actually receive the award? Did it feel like being in Rio at your Olympic medal ceremony again, or was this a different feeling?
Yeah, it was a bit of a different feeling and a really great one, [as] it was nice to have the whole American sailing community there. [There was a] unity about it- how I wouldn’t be able to do what I did in Rio if it wasn't for the people [who] were in that room.

So in a way, it was great to share that with everyone and have a little chance to acknowledge all the people that helped me get to where I was in Rio.

Where does your US Sailing Rolex Yachtsman of the Year Award rank on your list of trophies/awards/medals that you’ve won in your sailing career?
Definitely one of the top-probably just below my Olympic medal.

So can you tell me just a little bit about what your life has been like post Rio? Are you preparing for another Olympic quad or are you pursuing your career track at the moment?
I'm actually currently working at a job for a sponsor of mine who helped me get to the Olympics, and I [will] be going back to school and progressing my career life, but [yes,] I do plan [on] going back [and] sailing in Tokyo for the 2020 Games.

Anything else that you’d like to add, for the record?
I'm honored to have been nominated-and even shortlisted-for [the] Rolex [Award]. There were a bunch of amazing competitors and a bunch of great sailors that were all in the bid for this year. So my hat’s off to them for being such great sailors, and for having such a great sailing community here in the United States.