You’d think a man who executes a swan dive off the keel of his sponsored 60-foot sailboat in a tuxedo or entertains Ewan McGregor at sea might exude a certain arrogance.

Not so for British sailor Alex Thomson. In fact, one of the first things he told me in our brief conversation at Manhattan’s North Cove Marina aboard his Hugo BOSS Open 60 was that he’s failed his first three attempts to sail singlehandedly around-the-world.

First, there was the structural damage in the 2004 Vendee Globe, some apparent breakdown of carbon fitting that caused boom trouble.

Then there was the keel damage in the Velux Five Oceans Race in 2006, when Thomson had to be rescued by fellow British sailor Mike Golding.

In 2008, yet another Vendee went unfinished – or un-started, rather – when a fishing vessel struck Thomson’s yacht, dismasting it as he brought it into port for the race start.

In an extension of this streak of bad luck, Thomson was hospitalized with appendicitis just two days before the 2010 Barcelona World Race, which he was to tag-team with sailor Andy Meiklejohn. (Though this setback wasn’t all that negative – Thomson got to be present at the birth of his son).

When we met him that Saturday night at North Cove, Thomson seemed far from disheartened. He was below deck at his navigation table testing and demonstrating electronics to some of the crew as we came aboard.

We weren’t exactly stowaways. Earlier in the day, Bjoern had ferried some of the BOSS sailing team across the Hudson to Liberty Landing Marina in Jersey City, where the boat was initially docked. The crew had to move it back over to New York, but ferry service wasn’t running. Bjoern’s SeaRider was, of course, and he took the crew aboard in exchange for a promise of beers and a tour of BOSS.

Thomson had a week of hospitality sailing ahead of him but was happy to tell us about his upcoming round-the-world attempt. The 2012 Vendee Globe gets underway on November 10, leaving from Les Sables-d’Olonne in western France.

Barring any health or dismasting concerns, Thomson will likely be at sea for some 100 days. The winner of the 2008 Vendee did it in 84 days – but that’s the advantage of a trimaran over a monohull. (The winner was actually FONCIA, which Bjoern recently photographed during the KRYS Ocean Race stopover in New York).

Perhaps luck will be on his side this time. The latest trip across the Atlantic to the states only took 12 days, and Thomson and co-skipper Guillermo Altadill finished second in last fall’s Transat Jacques Vabre.

It’s probably true, then, what they say about Thomson on the Vendee website: “The day he makes it all the way round, Alex will be a real threat.”