Nothing like enjoying a beer on the water.

It’s awesome. Peroni’s a great Italian beer.

By the age of 24, you’ve already worked your way to be ranked as #1 Match Race Sailor in not only the U.S. but the world.

It’s kind of crazy. Sailing was just a dream of mine from growing up in the Virgin Islands. It was picture-perfect conditions everyday of the year so a bunch of my friends and I would go out on our own and sail to other islands. We never had any coaches, we just pushed one another and it became our passion.

Were there any sailors who you idolized growing up?

There was one guy in particular, Peter Holmberg. I remember I was probably about 10 years old when I saw him match racing and that’s when I knew it was something I wanted to get involved in.

Why did match racing appeal to you as opposed to other styles of competitive sailing?

It was the whole fast-paced nature of it. You’re only racing one other boat so it’s really a quick, aggressive and competitive style of sailing. There are hundreds of match race regattas all around the world for you to choose which ones you want to go to. Each event has a different level of competition so as you start doing better at some of the smaller ones, your ranking goes up and you can start competing in the next level.

What brought you to Chicago from the Virgin Islands? 

When I was 18 I went to school at Boston College and studied economics. I was on the sailing team there and during the summers I would come out to the Chicago Yacht Club and coach the youth match racing program. I did that for three summers and eventually met Don Wilson, who started the Chicago Match Race Center. This was before we had all of these boats here. There were actually only two boats back then, no houseboat or anything. We would just come down on Tuesday nights and go out sailing.

Give us the run down of a typical day for a match race sailor.

We race during the day then come in at night. In match racing you run 10 to 20 15-minute races a day and then you’re back on shore after that, have a few beers and go to bed.

US One Sailing TeamUS One Sailing TeamUS One Sailing TeamUS One Sailing TeamUS One Sailing Team

You’re the youngest sailor competing in the Alpari World Match Racing Tour. What has set you apart?

I think the biggest thing has been my passion. Whenever you’re passionate about something you love, you just want to keep excelling in it and do it for the rest of your life. I was able to find some great guys to sail with and go from there.

How did you put together your team US One?

It’s a bunch of buddies that I’ve met throughout my sailing career. It’s an enormous community but at the same time you keep seeing the same people over and over again and that’s how you develop these bonds and become good friends. They invite you on a boat that they’re sailing on and you do the same for them. I’ve raced against these guys probably more than I’ve sailed with them. They’re all professional sailors that sail with me for free which is nice but obviously they’ve been getting a little bit of the prize bonus we win at big events. 

What did you buy for yourself after winning your first big prize bonus?

I’ve been paying off some college loans first off but as far as fun stuff comes I’ve just been doing some trips with my girlfriend and hanging out. We went to Bitter End Yacht Club last year and stayed there for a week and a half, which is near my neck of the woods where I grew up. The prizes have been able to open up even more opportunities for me to travel.

Is it difficult to maintain relationships as a globetrotter?

My girlfriend Stephanie also works at Chicago Match Race Center so it’s pretty easy for me. I actually met her in England at the Youth Sailing World Championship event. She was sailing for the U.S. and I was sailing for the Virgin Islands. We didn’t start dating until two summers ago and then she came out and started working with me after graduation.

Favorite spot to race?

Definitely back home in St. Thomas. It’s beautiful everyday of the year there.

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The weather in Chicago must have taken some getting used to.

Yeah, this is great though don’t get me wrong. You guys have been on the lake before so you’ve seen the skyline here. Chicago is one of the best cities you can spend a summer in. That’s probably one of the biggest reasons that I moved here.

After making a comeback in the Chicago Match Cup, how did it feel to take the lead and win?

It was pretty crazy to be honest with you. We were in a really tough spot going into the finals. The first to win three points was the winner and we were sailing this Australian guy, Keith Swinton, that started off really strong. He beat us in the first two races so it came down to us having to win the next three in a row in order to be the champion, which was pretty nuts. After the third race we had a bit of an issue with our spinnaker, a big hole ripped in it but we were still able to just barely hold on to the lead. A big crash in the second race gave Keith a penalty so we were able to take that one from him as well. Going into the last race I was like, “If we’ve gotten this far we have nothing to lose,” and we just sailed really well after that.

What neighborhood do you live in? 

I live right in the Lakeview, Wrigleyville, Boystown area.

Favorite restaurants?

Probably Cozy Noodle and Rice right here in Lakeview, the Thai food there is awesome. Also there’s a little burger joint right up the way here called Rock’s that I really like.

What’s next for you?

Now that this is all accelerating upwards quickly it’s time to think about doing more professional sailing and maybe leaving the coaching aspect behind for a bit. I know some guys who’ve been doing this their entire life even up until their 60s so the longer I can do this, the better.

If you could have a drink with anyone, who would it be?

Steve Jobs.


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