OSTAR Winner Reflects on Humble Beginnings

For Jonathan Green, who sailed his 35-foot Beneteau to victory in the OSTAR, getting to the starting line was the real test.
Jonathan Green
Jon sets the autohelm on Jeroboam Sampson Jacobs

In his late twenties, Jonathan Green of Boston, Massachusetts, had no idea how to take care of a sailboat, or even how to operate one, for that matter. So with the insurance money from a car accident, he decided to buy a Clipper Marine 30-footer that he found in the nearby city of Quincy. He re-named it Sink Me II, as if he’d already sunk a first ship.

“I had no idea what to look for in a boat,” he said. “I pretty much bought the second boat I saw.”

Now in his early forties, it’s an understatement to say that Jon has learned how to handle a boat. Days after he’d successfully finished the 2013 OSTAR, or, the Original Single Handed Trans-Atlantic Race, a northern crossing of the Atlantic Ocean against prevailing winds, he invited me to hop aboard for a daysail on Jeroboam, the Beneteau Oceanis 351 sloop he campaigned from Plymouth, England, to Newport, Rhode Island.


While a strong headwind blew, I heard the story behind the only American to enter this year’s race. We sat back and let the auto-helm guide the sloop close-hauled while we chatted and enjoyed the fine mist that washed over the port hull.

Our carefree afternoon was momentarily interrupted when Jon received a call from the OSTAR officials. Jeroboam had come in first place overall, taking into account the handicaps that were applied to faster boats, such as Andrea Mura’s Open 50 Vento Di Sardegna that finished the 3,000 nautical mile race in fewer than 19 days.

How far he’s come. Years ago, when Jon was shopping for his first boat, he knew he couldn’t afford an apartment, so he decided to be a live-aboard from the beginning. But first he needed to finish some work on Sink Me II—the rudder was rotted and had to be completely re-built.


“So there I was during the holidays with a little Christmas tree set up in the front seat (of my car), while I slept in the back seat” Jon said, laughing. “Those days were the best.”

Jonathan Green on his Beneteau Oceanis 351
Jon enjoys the day while Jeroboam sails herself. Sampson Jacobs

Once he had moved aboard in Constitution Marina on Boston Harbor, Massachusetts, Jon made friends with sailors living in the area and started to learn very quickly. He absorbed everything, from how to take care of his boat’s engine, to the navigational rules of the road. Eventually after learning on other people’s boats, he was brave enough to push off and sail his own.

After living on Sink Me II for three years, Jon upgraded to Jeroboam, whose hailing port is Marblehead, Massachusetts. According to Jon, the delivery of Jeroboam to the starting line was actually harder than the race itself. Jon had to battle through storms across the entire North Atlantic. During one storm Jon’s boat had three knockdowns and an inversion.


“It was surreal,” he said. “My mind couldn’t even comprehend that my boat was upside-down, until I said out loud, ‘I’m upside down!’”

Limping into Horta, in the Azores, on only a jib, he didn’t know if Jeroboam would even make it to the starting line. The wind turbine had burned out and the radar reflector had been sheared off the mast, among other damage. Overall, to fix the boat was going to cost a lot more money than Jon had in his budget.

Jon going to the cockpit
Jon returns to the cockpit from setting the jib pole. Sampson Jacobs

Luckily, people started to come out of the woodwork to help him with the repairs. Friends and family helped to buy the necessary parts and supplies that he needed to get Jeroboam into racing condition again. One week later Jeroboam was out at sea again and on course for Plymouth, United Kingdom.


It’s ironic that Jon crossed the finish line in Newport, relatively unscathed. He had one little debacle with the head during the race, but came in sixth over the finish line in just over 22 days.

Jon has raced the Bermuda One-Two race twice, and has also competed in the Newport Bermuda race twice. His immediate plans were to return to Marblehead, and pick up where he left off, as the managing director of Brook Venture, a venture capitalist company, north of Boston. Jon is considering a round-the-world race, but he knows he won’t be able to finance it himself, so he’ll need to find sponsors.

Samuel Stiles, a.k.a Sampson Jacobs, a journalism student at the University of Rhode Island, interned with Cruising World magazine in the summer of 2013. An avid photographer, his goal is to become a live aboard sailor and writer. Log on to for more details about the OSTAR.