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One Last Time

2009 April 3
Al D'Alessandro opens a file cabinet in his Marblehead, Massachusetts office and rummages for information about past boats, crews and races. The octogenarian is looking for evidence of his first Newport-to-Bermuda Race in back in 1970.

"Seems like a long time ago," he says. "I guess it was."

Thirty-nine years to be exact. Al was 42-half English, half Italian, Harvard educated, former Navy intelligence, successful businessman, seasoned sailor, strong and able.

To put it in perspective, Richard Nixon was President the year Al sailed competitively to Bermuda for the first time. It was the same year Thor Heyerdahl set sail from Morocco on the papyrus boat Ra II to sail the Atlantic, the year of the Kent State shootings, the My Lai massacre, the release of Black Sabbath's debut album and the disbanding of The Beatles. It was the year Chevrolet introduced the Vega, Ford the Pinto, and American Motors the Gremlin. Tina Fey, Matt Damon and Uma Thurman were born. Janis Joplin, Jimi Hendrix and Charles de Gaulle died.

Al is counting on his fingers, trying to figure out just how many times he has done the Newport-to-Bermuda and the Marblehead-to-Halifax races. His best guess: 17 of each.

"Al has logged more than 150,000 offshore miles," says his wife, Joanne, 62, herself an accomplished offshore sailor renowned among friends for gourmet cooking while underway despite rambunctious weather. "Al's a long-distance runner, not a sprinter. He's like that in everything in his life-very deliberate. He's the tortoise not the hare."

Al nods, confirming her arithmetic and her personal assessment. He's reading off names of former crew, some of them now deceased. With each, there's a snippet of a story, a cryptic remembrance. Some are recalled fondly, others less so.

"Al is truly an offshore sailor," says Joanne, who met Al in a North Shore boatyard and married him a couple years later in 1997. "He begrudgingly races around the buoys."

Al smiles sheepishly and says, "You know the definition of cruising? It's how you get from one race to another."
Both he and Joanne laugh easily at the core of Al's existence.

Next February, Al turns 82-a fine age for a skipper who loves the sea. He's already thinking about the 2010 Newport-to-Bermuda Race-the logistics, the boat, the all-important crew. He's also getting ready for this summer's Marblehead-to-Halifax. Yet for a self-taught sailor with such vast bluewater experience, culling advice from him is like extracting a molar with a Leatherman. So I ask, what makes a good crewman on the race?

"Well that's a simple question," he says. "Tenacity, some sailing ability, a little bit of courage, and it certainly helps to have a sense of humor."

That's it?

"Yes. That's the minimum. And if you're going to race, the boat's name must start with A."

Why so?

"Because it gets you to the head of the line at registration."

Joanne rattles off the names. There's their present vessel, Alexis, an Aerodyne 38. Before that was Arbella, a Taylor 40, preceded by Allegro Duo, a Morgan, and the original Allegro, a 30-foot sloop.

What about training?

"For your own good and the good of the boat, do a return first," says Al. "If you screw up during the delivery, you're not costing everybody the race. Bermuda is an endurance thing. If you enjoy dealing with the elements, that and skiing are the ways to do it."

Joanne says return trips are Al's version of a vacation, with a crew that's likely shorthanded, seasick and inexperienced. Ain't in the truth, Al says without uttering a word.

So tell me some stories, I say.

"Well, I've gone overboard a couple of times."

"Not on my watch," snaps Joanne, describing Al clinging to a stanchion in choppy Buzzards Bay after the boat broached with the spinnaker flying.

"That's right," says Al. "And I was bellowing the whole time, 'Don't cut the chute.' And they didn't."

Al made it back aboard unscathed, but on other trips there were injuries, including one that left him below deck shouting orders and using a Playboy magazine as a knee splint.

"Finished the Bermuda race four times without power," he says, recalling the reasons: an air leak in the fuel line, a faulty insulated starter motor wire, wet battery gels, and somebody poured gasoline from a jerry can into the diesel engine fuel tank.

On one Bermuda crossing, the wind slacked, leaving them listless in the Gulf Stream. To fight boredom they filled the cockpit with seawater and floated rubber ducks as a fleet of northbound tallships bore down upon them.

Then there was the year Al overshot the mark. Once the error was detected, Al shouted out, "Jesus Christ, we're south of Bermuda," at which the crew cracked up laughing and later made T-shirts with Al's words emblazoned on the front.

The skipper chuckles merrily at the memory.

"We had the same crew for years," says Joanne, who has done her share of big races. "It became like a family. The joy was that we all loved offshore sailing."

Al says they'll do Marblehead-to-Halifax this summer and then pull together another crew for next year's Newport-to-Bermuda.

"No more Bermuda," says Joanne, firmly. "You've done enough."

Clearly not swayed, Al doesn't respond. Instead, he yanks another file folder from the drawer with names and phone numbers of potential crew.

Joanne shoots him a look, a silent reprimand in front of a stranger. But Al isn't pay mind to anything but the information in the folder, so Joanne tries the same message aloud.

"You're not going to Bermuda again."

Al's eyes suddenly come alive, a smile breaking across his creased face. He closes the folder. "Oh yes I am," he says. "One last time."