Rum Dog hits the beach (again)

Sailboat and owner have an interesting history.


Updated Aug. 28

A 26-foot Pearson sailboat named Rum Dog came hard aground at the Little Bridge Inlet over the weekend. Chilmark resident Brian O’Gorman, who said he owned the vessel, told The Times it broke its anchor from a nearby location off the beach. 

“I lent it out to my friend to take his son sailing,” he said. “And when the wind is from the southwest — it’s a lot that way in the summertime — this is a perfect anchorage. But it came around from the north …”

On Monday afternoon, the sailboat was heeled over to one side in the shallow water of the inlet. O’Gorman’s friend John Chivers, whom he referred to as “Hercules,” chipped barnacles off the hull with a paint scraper as O’Gorman looked on from an embankment. By his feet was Chewbacca, a golden retriever rescue dog. Chewbacca was almost tapped to help secure lines on the Rum Dog, but O’Gorman said the dog didn’t have his sea legs (paws) yet. “He’s not that experienced yet, but he has the spirit for it,” he said. 

O’Gorman said he bartered for the Rum Dog with Chef Sean Yancey in exchange for doing some work on Yancey’s house. Yancey couldn’t immediately be reached to confirm this. However, Tisbury harbormaster John Crocker said he believed this to be true. The Rum Dog, Crocker said, was moored in Tashmoo before O’Gorman acquired it earlier this season. Crocker said he feared trouble from the get-go once O’Gorman took control of the boat; however, he gave O’Gorman the benefit of the doubt and let him operate the sailboat in Tisbury waters. This was short-lived. Crocker said O’Gorman failed to adhere to directions from the Harbor Department regarding mooring use and other issues. O’Gorman is now banned from Vineyard Haven Harbor and all other Tisbury waters, Crocker said. O’Gorman described Crocker’s decision as “very abrupt.” He confirmed mooring issues were involved. At one point, O’Gorman said, he was on a town mooring, and then another mooring where there may have been a misunderstanding. Ultimately Crocker told him he could stay if he ponied up a $1,500 mooring fee, he said. 

On Sunday, O’Gorman said, the Oak Bluffs Harbor Department and a tow boat company came onsite, but declined to pull the sailboat because of low water and a nearby sandbar. 

Oak Bluffs harbormaster Todd Alexander said he summoned TowBoatUS to secure the Rum Dog on Sunday while it was still at anchor because it looked in a perilous state. But the sailboat had broken free and grounded by the time TowBoatUS arrived. Alexander said he later went there himself with Oak Bluffs Police. 

“We know it’s there,” Oak Bluffs Police Sgt. Michael Marchand said. Alexander said he expects O’Gorman to free the sailboat at his own expense. 

The Rum Dog beached earlier in the summer on East Chop during a July storm, Alexander said. O’Gorman said the anchor line broke then too. O’Gorman’s nautical incidents are beginning to echo David Hawkins’, Alexander said. Hawkins’ numerous maritime misadventures have raised red flags with many harbormasters on the Vineyard and the Cape. 

Crocker said he hoped a bill taking shape in on Beacon Hill will strengthen the tools harbormasters have to regulate problematic or inexperienced mariners. 

O’Gorman said he planned to wait for high tide Monday, when his nephew planned to help tow him out. By sunset, he said, he expected the wind to have diminished too. But as of Tuesday morning, the boat remained stranded and as of mid-day on Wednesday, the boat was taking on water and being pounded by small waves. The boat has moved toward the middle of the channel.

Beached boats haven’t been O’Gorman’s only travails. This past Christmas in Cambridge, O’Gorman said, he was ambushed by two men with a baseball bat. He was hit in the back of the head and in the mouth, he said, and is missing several front teeth because of this. “Almost killed me,” he said. 

The attack landed him in Beth Israel Deaconess Medical Center, and later Martha’s Vineyard Hospital. 

He said he’s been unable to work, and is hoping for help through a state victims’ fund.

O’Gorman said he is a Massachusetts Maritime Academy–trained captain, and that for 23 years his late father ran the vessel Que’tal on charters between Menemsha and Cuttyhunk. 

While he had been anchoring off Chappaquiddick, O’Gorman said he is hoping to get the sailboat to Menemsha. 

“We’re happy to add anyone’s name to the mooring waiting list,” Chilmark harbormaster Ryan Rossi said. At present, he said, about 75 people are waiting for moorings.

Updated with the boat’s status as of Wednesday.


  1. Whoever was operating the vessel wasn’t very bright. First, they were anchored up right in the middle of the small bridge channel and then they anchored right outside the entrance. Capt. Hugashore was anchored too close.

  2. This is truly a sad avoidable situation. It was clear from the initial purchase of the boat that the owner would have challenges. Forcing the boat out of Vineyard Haven so it becomes the problem for another Town is no solution. There needed to be communication and a coordinated effort with other Towns and agencies to work with the owner to prevent this..

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