The last two Steamship Authority captains from Martha’s Vineyard have officially retired, leaving only off Island-based officers to run the Woods Hole route.

Family and friends threw a party for Michael Mazza and Sean O’Connor at the Portuguese American Club in Oak Bluffs earlier this month, and this week the two former shipmates and longtime friends met with the Gazette to talk about their years with the increasingly-embattled boat line.

When a young Sean O’Connor signed on as summer deckhand aboard the old, side-loading Naushon in the early 1970s, he said Steamship Authority jobs were in demand and he considered himself lucky to get one. Boston politicians and other influential men would secure summer SSA jobs for their children, he said, naming several he served with in the 1970s and 1980s.

A building boom on the Vineyard, followed by a wave of new SSA ferries acquired in the 1980s, spurred his advancement, Mr. O’Connor said.

“By the time I was 30, I was captain year-round,” he said.

Mr. Mazza began his maritime career in the Gulf of Mexico before joining the Steamship Authority in the 1980s.

The two men served together aboard the old Islander, with Mr. O’Connor the junior captain and Mr. Mazza the junior pilot before the ferry was retired in 2007. They worked together again aboard the M/V Martha’s Vineyard, which Mr. O’Connor captained for 15 years.

It was aboard the Island-bound Martha’s Vineyard, some 30 years ago, that Mr. O’Connor married his wife — whom he met through Mr. Mazza — in a ceremony performed by Joe Sollitto, then clerk of courts and now Oak Bluffs representative to the Steamship Authority’s port council.

“It saved a step,” Mr. O’Connor said, smiling. “We got married on the way over and then went to the reception. All the people were already on board.”

At the time of their retirement, both Mr. Mazza and Mr. O’Connor were captaining freight boats, a perk for senior officers because the vessels are simpler to operate.

“Your problems on the [passenger] vessels are elevators, bow and stern doors, lunch counter,” Mr. O’Connor said.

The freight boats have none of those trouble spots.

Speaking with the Gazette, both captains were frank about where they say the Steamship Authority has gone wrong over the years since. The boat line’s current personnel woes can’t be pinned entirely on general manager Robert Davis, Mr. Mazza said. Mr. Davis recently announced he would be stepping down in October 2025.

“He inherited this mess. This has been coming. We’ve been telling them for years,” he said, blaming successive administrations at the Steamship Authority for poor planning and unwise labor cuts.

“They were like, ‘Don’t worry, somebody’s always waiting for these jobs.’ Not any more,” Mr. Mazza said.

“I think basically, the idea for years [has] been cut the crew, cut the crew, cut the crew, and now you’re down to a point where if one or two guys call in sick, you can’t run. That’s a foolish business plan,” he said.

“We started seeing good young people come in the last two or three years and then go, ‘You know, I don’t think so. I’m gonna go try elsewhere,’” Mr. Mazza said.

Without younger workers in entry-level jobs, the Steamship Authority will have trouble staffing every position above them, the captains said.

“Because there aren’t these stepping-stone positions, they’re not getting the captains, they’re not getting the pilots,” Mr. O’Connor said.

The trouble began just over a decade ago, Mr. Mazza said, when boat line management stopped providing on-board meals for crew members.

“Some of the cooks were spectacular. We always had homemade soup seven days a week. They always had a tuna salad and a lot of [cooks], if you didn’t like what was being served, they’d make you something else,” he said.

Turning the kitchen into a break room, where crew members bring their own meals and clean up afterwards, has done away with the only opportunity for them to gather before a trip, Mr. Mazza said.

“That lunch or breakfast together bonds the crew,” he said. “They took that away about 10 or 11 years ago, and since then, they’ve had problems finding help.”

Mandatory drug testing, both pre-hire and at random during employment, is also dissuading people from shipboard work, the captains said.

“You can’t smoke pot on your days off,” Mr. O’Connor said, with Mr. Mazza continuing the thought: “So we basically lost the youth, and then we used to get the older guys that retired from their jobs, and then they’d come here and do what, 10 to 15, years...and then with Covid, we lost them,” Mr. Mazza said.

The Covid-19 pandemic also pushed a sharp increase in the Island’s population — evident in the amount of freight traffic that’s heading to the Vineyard — creating even more pressure on remaining crew members, the captains said.

Ever-present security cameras are another disincentive for prospective hires, the captains said, and the jobs themselves are demanding.

“I had to get married on a Wednesday, because I worked every weekend,” Mr. Mazza said.

Summer vacation time was prohibited until 1989, Mr. O’Connor said.

“From June 15 to September 15, you did not get any time off [until] that got negotiated,” he said.

Crew members worked through the winter holidays as well, Mr. O’Connor said.

“You understood, if you came to work here, that, yeah, [you] might not be home on Thanksgiving Day. You might be gone on Christmas afternoon. We work every single holiday,” Mr. O’Connor said.

Premium pay for holiday work doesn’t change the fact that crew members can’t be with their families, Mr. Mazza said.

“These younger people seem to be more interested in having the day off than making the extra money,” he said.

Mr. O’Connor just renewed his Coast Guard captain’s license, which is good for two years and can be renewed as long as the bearer passes a physical. But he won’t be going back to work, he said. An avid golfer, Mr. O’Connor plays in tournaments and goes motor-homing with his wife in the off-season.

Mr. Mazza said he’s going to take a leaf from the O’Connors’ book.

“I told my wife last week, I will never, ever spend another July and August here. I’m gonna buy a camper,” he said.