A Race for the Ages

Cape Cod Life  /  May 2021 / ,

Writer: Rob Conery

A Race for the Ages


Cape Cod Life  /  May 2021 / ,

Writer: Rob Conery

After 50 years of Figawi, nobody is wondering where we are anymore.


Time and the accretion of myth have clouded many details, but Bob Horan, his brother Joe, and Bob “Red” Luby competed in the debut regatta. It was an, “I can sail my boat to Nantucket faster than you, and let’s make it interesting!” kind of challenge after a few drinks at Baxter’s Boathouse in Hyannis.    

Luby won the race on Memorial Day 1972.  

Luby would later say of that first race that “Nobody had anybody onboard who knew how to sail a boat, but it was a lot of laughs.” Indeed, at one point Luby was spelled at the helm and in the time it took him to visit the head, the neophyte crew had managed to turn the boat on an opposite heading, essentially sailing back toward Hyannis as fast as they could!

The first race ended with a jarring anti-climax.    

Nobody was waiting to hail the triumphant sailors, indeed the Nantucket Boat Basin was closed! The second year, by word of mouth, Figawi grew to 15 boats. Stan Moore won aboard a crazy-looking contraption called Moby Dick.  

Puritan of Cape Cod’s Howard Penn brought his redoubtable organizational abilities onboard and the newly organized Figawi Committee booked Cap’n Tobey’s Chowder House on Nantucket’s Straight Wharf to host the 1973 post-race party. By 1979, they added a lay-day on the island; a Sunday without racing meant they could relax, maybe throw a clambake.  

1979 also brought the first Figawi tent, a modest affair perched on the end of New Whale Street.

Today Figawi is not one event, as much as several overlapping carnivals.  

Certainly, it is a great regatta. There is a palpable sense of camaraderie among the crews, captains congratulate or commiserate, and to walk the docks with a just-won silver trophy in your hands is to be granted temporary celebrity status. But Figawi is also an all-the-trimmings lobster clambake. It is a dance party—boisterous live music fills the big party tent while revelers take their life in their hands on the drink-slick dance floor. It is a joke telling session as the tent temporally becomes a stand up comedy revue. It is a high school regatta, it is a fundraiser, and it is mainly a chance to get together, sail fast, and see friends, as the event heralds the unofficial start of the summer season. 

It wasn’t always smooth sailing.  

1980 is remembered by many as the “Hurricane Figawi.” When one boat pitch-poled (flipped forward end-over-end) and later sank, it was Camelot to the rescue!  Bob Labdon plucked the four-man crew from the cold water in a remarkable display of seamanship. It was so rough—10- foot seas and the wind gusting over 40-knots—that the 48’ Camelot’s bow was rising so high as to expose the front half of her keel; when they’d plunge into a trough, crewmember Brooks Smith would pluck them from the icy sea. Figawi committee member Charlie McLaughlin was on the scene and later described, “But for their skill, there would have been four deaths.  It was the finest act of seamanship I have witnessed in 65 years on the water.  

The 2011 Figawi was so rough—with the wind “blowing like stink”—that nine of 13 divisions were ominously listed with “no finishers due to weather.”

Today, Figawi is made up of hundreds of boats, thousands of racers, and thousands more “racer chasers” who come by motorboat, ferry and airplane to join the scene. You know something has gone next-level when football party boy, Rob Gronkowski shows up, as he did in 2016.  

CAPTAIN.The captain, or skipper, “drives” the boat.  Whether using a tiller or a steering wheel, he controls the helm—it’s his show. He gets the glory, he takes the blame.   

OWNER.Many owners bring in a “hired gun” skipper to give them an edge. The owner has one important job, he writes the checks!  He also controls the all-important wristbands (required to enter the party tent) and the limited supply of red Mt. Gay hats emblazoned with the Figawi Race logo and year; extremely valuable bargaining chips during the weekend, and later instantly recognizable from Chatham to Beacon Hill to Wall Street. The skipper may get the glory, but the owner keeps the trophy.  

TACTICIAN/NAVIGATOR. Also known as egg head, the professor, spreadsheet Pete. This guy will have dials, anemometers, gauges and stopwatches swinging from his neck. If he’s wearing a watch, it’s digital. He can do algorithms in his head, but is also prone to locking his keys in the car with the lights on.  

GRINDERS. Or goons, or gorillas. These are the guys wrestling the handles on the big drum winches that keep the sheets (lines that control sails) in place and adjust them on the fly. Grinders can be identified by their huge shoulders and powerful thirst.  

BALLAST. Also known as rail meat, rail monkeys. These least experienced of crew members all sit on one side to help balance the boat, then crab scramble to the other side when the boat tacks (changes direction into the wind). The motion of a sailboat through the water is the sum of the forces acting upon it. When those big sails are full of wind, despite the heavy keel down below, the boat leans over (heels). Rail meat collectively act as a counterweight to this heeling force. Totally exposed on the windward rail with their legs dangling over the water, they take the worst beating of all the crew; cold waves, cold spray, and aching back muscles—they earn those wristbands the hard way.  


I chanced into the 1994 Figawi on a second-hand invite. 

I was rail meat on my neighbor’s O’Day 29. The owner (quite literally, a rocket scientist) to maximize the efficiency of the propellor (less drag though the water) wrote a computer program the night before the race!  

We avoided collisions with other boats (narrowly), missed slamming into a metal harbor buoy (by an even more narrow margin), and sailed across the finish line in fourth place, earning the owner an engraved silver platter.  

Over the years I crewed on a J-35 and a Nonesuch 30.  I have occasionally cheated and accepted an invite on a motorboat—what some sailors derisively refer to as “stinkpots.”  

By 2014 I had been promoted to de-facto tactician amongst a crew who didn’t know jib sheets from Egyptian sheets. We started in dead last—13th in our class of, well, of 13 boats—but after an astute tactical change we began to run down the field from behind, overtaking one boat after the another (a thrill that can only be experienced, not described) and earning our skipper second place and a shiny silver cup.  


It is a timelessly enchanting notion—to pack a bag and set sail for unseen shores. Unlike many regattas, which simply circle buoys on a created course, Figawi is actually a race to someplace. 

Sailing is all about the hardware; trophies are enduring monuments. Indeed, the oldest trophy in sport is the America’s Cup.  

Figawi’s free-spirited festivities draw boats not only from the Cape & Islands, but attract the best from Newport/Marion/Marblehead ports also.    

Bob Solomon comes all the way from Indiana to skipper Perfect Summer. A veteran of 28 Figawis, from 2014 through 2018, Solomon would invite wounded veterans aboard, not as mascots, but actually to help in the crew. When Solomon departs Hyannis harbor and sails up the jetties with a massive—I mean drive-in movie screen massive—US flag flying from the aft stay, he has set the tone for the whole weekend. 

Figawi has always attracted big talent. Bill Koch sailed Matador to first place in A Class in 1986 and 1987 (five years later he went on to win the America’s Cup). The late Senator Edward M. Kennedy won F Class aboard his beloved schooner Mya in 1989.  


A garrulous walrus of a man, Jeffery Foster is credited with hosting the very first joke telling session in 1977. Foster had run hard aground in Nantucket harbor and started telling jokes to pass the time until the rising tide freed his keel. Today, the Band of Angels—a troupe of merry pranksters who perform classic bits—host the event on Sunday in the tent, where the jokes are 50 shades of inappropriate and which they bill as, “A champagne brunch, you bring the brunch.” We lost Foster in 1997. Today the winner of the team race is awarded the Jeffrey Carter Foster trophy in his memory.  

Warren Thatcher “Barney” Baxter, Jr., passed in 2000. He was a genial host and enjoyed having the unofficial post party every year at his waterfront bar at the end of Pleasant Street.  To this day, the original Figawi trophy hangs on the wall in the Boathouse Club of Baxter’s Boathouse.  

Ed O’Neill was an accountant by trade, a photographer by inclination and a bon vivant by nature. Figawi’s official photographer enjoyed rock star status on the docks and in the tent until his passing in 2013. 

Both Horan brothers and “Red” Luby are gone from us now, as are senator Kennedy and Pam Duggan.

In 2012 Figawi lost its true exemplar, Howard Penn. Affectionately known as the Silver Fox, “Howie Figawi” was a tireless promotor of the event since 1973. He could always be seen a little behind the scenes, a bemused smile on his face. The Howard K. Penn Spirit Award Trophy is awarded annually in his name.   

But Figawi sails on, largely due to the organizing skills and social graces of many people who volunteer their time to make this a memorable event for all—Chris Standish, Tony Prizzi, John Osmond, Milton Salazar, Leo Fein, Tom Duggan, Donna Nightingale, Joe Hoffman, Chris Kelsey, Bob Haag, Russ Wilkins, Andrew Nugnes, David Crawford and Shelley Crawford Hill.  

Walking into Hyannis Yacht Club on the Friday before the race; the adrenaline-soaked semi-controlled chaos at the starting line; scores of popping spinnakers splashing colors that fill the horizon; finally sighting through binoculars the bouncing, wavering, bobbing buoy that marks the finish line; easing around Brant Point Light on the island, seeing that familiar field of masts in the Boat Basin, looking up at those Nantucket church steeples—knowing that you’ll soon be folded into a moveable feast for a weekend of genial, plaid-clad wanderings.  

And every year, the last song on Sunday night in the tent is “God Bless America” as Figawi gives thanks to the Americans who made the ultimate sacrifice for this country.  And let me tell you, from tough-guy crew members to wives and girlfriends to the saltiest wharf rat, there isn’t a dry eye in the house. 

Rob Conery has sailed in over 20 Figawis without sinking any boats (but he did fall off one once). He splits time between his native Cape Cod and the mountains of Maine, where he runs a fishing camp called Black Jack Fly.

Learn more about Figawi, and check out the 2021 schedule at figawi.com!

Figawi is also a Cape Cod LIFE Best Of Winner! Check it out here!

Rob Conery

Rob Conery writes a weekly fishing column for Cape Cod Times. A graduate of the University of Massachusetts, he splits time between a hobo camp in western Maine and his native Cape Cod where he has spent 45 consecutive summers walking distance to Lewis Bay. He has written many articles for Cape Cod LIFE including a recent piece on Cape Cod and Islands divers, and his novel Winterland is available on Strawberry Books.