Gary Jobson has made a living as sailing’s most dedicated advocate. He won an America’s Cup alongside skipper Ted Turner in 1977, bagged two Emmys for coverage of sailing at the 1988 Olympic Games and the 2006 Volvo Ocean Race, and was honored with US Sailing’s most prestigious award, the Nathanael G. Herreshoff Trophy, for outstanding lifetime contribution to the sport. More recently, he won his toughest competition yet: a two-year battle with lymphoma. In October, CL caught up with Jobson on a rare morning in his Annapolis office to talk about his first sailboat race, a lesson from Ted, and overcoming cancer.

> Sailors have a unique ability to get along with each other. On a boat, those are your brothers and sisters; you’re close.

> Sailors can also be cliquish and often über-competitive —on the water, on land, and in everything they do. As I get older, I am slowly learning that winning at all costs isn’t everything and that what you learn is more important than how you do.

> I’ve been in more than 5,200 races, sailed 62,000 miles, written 16 books, produced 720 television shows, written 900 articles, had 2,350 speaking engagements, and visited 370 out of 1,000 yacht clubs [throughout the world]. 

> My first sailboat race was when I was 6. I crewed on a sneakbox, a 15-foot wooden, gaff-rigged catboat, on Barnegat Bay. I was given three jobs: keep the boat dry with a bucket and sponge, hold the course chart, and don’t ask dumb questions. So it was the first race, and all the boats were behind us. I hadn’t said a peep, the boat was bone dry, and the skipper asked me to point out our next mark, but I didn’t know because the course chart had fallen out of my pocket. We went to the wrong buoy and lost the race. I learned a lesson from that, and for the rest of my life, I’ve always known what the course was and had a goal. 

> It was 2004, and I was lying in the hospital in Baltimore after my stem cell transplant. I was 145 pounds. (I’m now 210.) I was really feeling bad for myself. I started thinking about the sneakbox race and how bad it was to lose the chart. I thought that if I could get out of that jam, maybe I could get out of this jam, too. I then realized I needed a goal. I said to myself, ‘I’m going to get up, and get out of this bed.’ I resolved that if I got out of the jam of being sick, I was going to help people and be more service-oriented. Since then, I’ve helped raise more than $32 million for the Leukemia & Lymphoma Society.

> I’ve lived in Annapolis for 32 years. Annapolis is a town that’s very accepting to newcomers. You don’t have to be born here to be accepted.

> Besides my parents, the person who has most influenced me is Ted Turner. He’s got this incredible work ethic, but what really sets him apart is that he’s a visionary. The biggest lesson I’ve learned from him is that the most successful people are those who do something that hasn’t been done before.

> My scariest moment sailing was in 1964. I was sailing an 111/2-foot Penguin on Barnegat Bay, and this unbelievable storm welled up. This thing was racing across the water—thick, black clouds—and the wind started to build. I was going really fast, and suddenly I lost control and the boat just exploded and capsized. I landed in the water under the sail. Thank goodness I had my life jacket on. The whole thing was over in 10 minutes. As a result, over the years I have erred on the side of caution.

> The first time I did a show for ESPN I had an on-camera with 30 seconds of copy to read. It took 30 takes to get it right. I suddenly realized this wasn’t so easy…

> I never pushed my daughters to sail. All of them were in sailing programs when they were young, but they suffered from the opinion of others that said, ‘You have a famous father, you should be winning.’ It was hard for them to excel because of that. They’ll go cruising anytime, but none of them race.

> The very best sailors are calm in the heat of battle, and I’m sure that translates to their personal lives. It’s the second-tier sailors who scream and yell. I wonder about their character. Great sailors—Dennis Conner,
Ted Hood, Buddy Melges—none of them yell.

> It was 1969, and I wanted to go to a concert with a friend of mine, but the 420 Nationals [a dinghy regatta] was in town. I couldn’t decide what to do, so I asked my dad. He said to go to the regatta, that I could go to a concert anytime. I still can’t believe I chose the 420 Nationals over Woodstock.