The Travels and Travails of the Coveted Whalers Cup

The Whalers Cup at The American Hotel following the 2018 races.

Last year, after the conclusion of the whaleboat races during Harborfest in Sag Harbor, Ray Pettigrew and Billy Martin were at the Corner Bar, celebrating another victory in the signature event of the village’s annual fall festival. Pettigrew and Martin had possessed the Whalers Cup — the winning trophy — many times before, as members of Team Whalers, the most successful rowing team in the history of the races.

Also at the bar that night were Roy Schoen and Dirk Early, members of the team sponsored by the Corner Bar, who had also been regulars in the whaleboat races over the years. It was, as expected, a lively night full of drinking and revelry, with Pettigrew, Martin and their other teammates celebrating their win, with the cup in tow.

But at the end of the night, it was no longer in their possession.

Early was greeted by a text message the next morning with a photo of the cup sitting on the passenger seat of Schoen’s rental car. His teammate, who originally hails from Sag Harbor but now lives in Colorado, was getting ready to catch a flight to California for a work trip. The text from Schoen was a message he wanted Early to pass on to Pettigrew and Martin: “Let them know the cup will be in California in the morning.”

At some point during the night, Schoen had swiped the cup from the winning team and taken it to the home of Virginia and Bruce Bennett, his brother-in-law, where he was staying while he was in town. Of course, Schoen did not actually take the cup to California. Later that morning, as he was heading into work, Bryan Boyhan from The Sag Harbor Express, which organizes the whaleboat races every year, saw Bennett walking toward him with the cup in hand, ensuring it was back in safe hands.

An almost-trip to the west coast is just one of the many adventures the Whalers Cup trophies have been on in the years since they have been the prize for the hotly contested whaleboat races. There are actually three cups — one passed around to the winning men’s team, the winning women’s team and the winning junior team — and there are fun and interesting stories surrounding them all. Perhaps more than any other community event, the annual whaleboat races are an intricate part of the Sag Harbor fabric of life, creating friendly rivalries that test the bounds of the word “friendly,” pitting lifelong residents who are often former Pierson High School classmates, teammates or co-workers against each other in a test of strength and stamina that is a nod to the town’s rich history as a world famous whaling port.

Early has been a part of the whaleboat races for many years — and he also built the wooden white whale that floats off Windmill Beach during Harborfest — and has been on winning teams three times, including once as a member of Team Whalers in their four-man boat. He said the short-lived kidnapping of the cup by his teammate last year caused a bit of drama, but the timely return helped keep things light.

“They were thinking about going to the cops saying he stole it,” Early said; it was unclear if this was said in jest or not. “But it was all in good fun. It was just sitting on the table, and everybody was partying, and they weren’t paying attention because we were all doing shots and drinking beers, so when it was time for Roy to leave, he just scooped the baby up and went back to Bruce and Vee’s with it.”

If the cup could talk, the story of its overnight kidnapping isn’t the only tale it would have to tell. Early shared another story about a celebration years ago, when he was on a winning team with Schoen and Warren Bramoff. They filled the cup with tequila and drank out of it while celebrating at the backside bar at the American Legion. They had beaten Pettigrew and Martin’s team that year, he said. After a few swigs of tequila from the cup, Early said Bramoff decided that the winning team would challenge the members of the runner-up team to arm wrestling battles.

“All four of us beat all four of their guys,” Early said. “That was probably 20 years ago.”

Aside from the joy of celebrating with the cup immediately following their victories, the winning teams are technically owners of the cup until the next year, but Boyhan said he typically tries to lure the cup back to the Express offices so he can take care of having the names of the winning team engraved on the trophies.

The Sag Harbor Whalers Cup trophy on 9/5/17

The whaleboat races have a long and storied history in the village, and were a feature even before Harborfest officially began in 1990. The Old Whalers Festival, which started in the 1960s, was the precursor to Harborfest, and whaleboat races were part of that event, according to Boyhan. After the OWF, the presence of a festival as an annual occurrence did not gain consistency until Harborfest started in 1990, but even after the Old Whalers Festival ceased to exist, there would be festivals in the town here and there to commemorate various things.

Boyhan said that in the first year of Harborfest, there was no trophy for the winners of the whaleboat races, and so he simply bought bottles of champagne for the winners. The next year, he asked Sag Harbor jeweler Dave Lee if he had any trophies in his possession that he could use. Lee dug up an old trophy and refurbished it, which became the first Whalers Cup. As women’s teams started to become a bigger presence, Boyhan went back to Lee with the same request, and he found another trophy. Eventually, Boyhan figured the event should have more formal looking trophies, so he had two matching cups made by a trophy maker in Massachusetts. The names of the winning teams are engraved on each one every year, with the junior’s cup added a few years back. The winning team is also presented with a silver plate with the team name and names of the crew members.

People with a sharp eye who spend a lot of time in Sag Harbor can spot the cup sometimes, depending on who the current winners are. The cups are often in the Corner Bar, displayed above the bar, if the reigning champions were sponsored by the team. Women’s teams sponsored by the Sag Harbor Liquor Store, led by Heidi and Hilary Schmitz, have also been proud owners of the cup several times, displaying it in their store. A women’s team sponsored by Brown Harris Stevens won the cup last year, and displayed it in the office. Jane Holden, who helped put together the team and who works for Brown Harris Stevens, said she regularly polished the cup and discouraged team members from drinking out of it, because she wanted to keep it nice. And, she added, “there’s not enough alcohol in there to kill all the germs.”

Last year’s winning women’s team from Brown Harris Stevens included Jane Babcook, Kim Kakerbeck, Cynthia Barrett and Clare Tenkarian. The cup sat proudly in the front window of the office at 96 Main Street, and was even brought to the company’s annual meeting with all the offices from the North and South forks, where it was feted and shared by members of the company.

For teams that were not associated with a certain business or storefront — like Team Whalers, which Boyhan estimated has won the cup a majority of the time — the big moment is always the presentation after the race. For many years, the presentation of the cup was done aboard a flatbed truck in town that was also used for the clam shucking competition.

“Somebody would bring a bottle of Budweiser and fill up the cup, and they’d get up there and make a big show of sharing the cup and drinking from it and passing it around,” Boyhan said of those celebrations. “Generally, the cup wound up in the Corner Bar, even if they hadn’t sponsored the winning team. But it was a place where everybody would meet, in some cases before the races. The cup would disappear sometimes, depending on who won it, but I always needed to get it back to send it out to be engraved.”

Often, Boyhan would try to make a point of displaying the cup in the front window of the Express, particularly in the years the offices were still on Main Street, as a way to promote Harborfest and the whaleboat races in the weekends leading up to the festival.

The Express was the cup’s rightful home in 2017, when a team it sponsored, led by captain Terry McShane, won the race for the first time. It sat alongside another trophy at the Express: a golden kickball, earned by winning a kickball competition among several other local newspaper organizations years ago.

Of course, the cup did not always stay in its hometown. Several years ago, a women’s team called the Indian Wells Wenches — comprised of East Hampton Town residents — claimed victory multiple times, from 2005 to 2007. The crew typically involved Helen McGuire, Lauren Walsh and Liz Pucci, as well as Cassidy Walsh, Meghan McGuire, Mary Cuomo and Dana Kalbacher in various years.

McGuire said that she and her teammates made a point of taking the cup off Long Island. There was a trip to Block Island, including a memorable stop at a popular bar called The Oar, patronized by boating people.

“We were very popular there,” McGuire said, adding that bringing the cup with them to the bar had one very distinct advantage. “It was a great way for us to drink for free.”

Another memorable trip was one where original plans went awry. The women had planned to bring the cup with them to a Red Sox game in Boston, but halfway there, they realized they’d left the tickets at home. So they went to a bunch of local dive bars in New London, Connecticut, where the ferry had dropped them off, with the cup in tow.

“It was something to show off,” McGuire said. “It’s like a puppy; people are really attached to it. It’s a big, beautiful trophy, and you drink out of it, and it’s just fun to have.”

McGuire said they mostly drank champagne or beer out of the cup, (perhaps a more conservative choice than tequila).

McGuire added that the Indian Wells Wenches team was particularly proud of winning because they were the first team outside of Sag Harbor to win the cup.

“There was a lot of brouhaha about that because Sag Harbor is very possessive of the cup,” she said. “We’d go in the Corner Bar and we were almost not served. There was a lot of drama in the whaleboat races. It was all in good fun, but the fact that the cup left Sag Harbor in those years was a huge deal.”

McGuire said that she and her teammates felt considerable disappointment after having to the return the cup when they were finally unable to defend their title.

“Once we lost it, it was like dead man walking down the wharf,” she said, laughing. “But it was an honor to have it. It really struck up conversation wherever we went with it.”