A Pirate Looks at 90: For Crab Shack's Capt. Jack Flanigan, life has been good

If you ask Capt. Jack Flanigan what he remembers most about life in the Lowcountry, he’ll tell you, “only the good things.”

If you ask his friends what they remember about him, the answers get a little more colorful.

The longtime owner of The Original Crab Shack on Tybee Island celebrated his 90th birthday on Aug. 8, along with several hundred well-wishers with stories to tell. The restaurant’s massive screened-in dining hall buzzed with those who have known this local legend since he and his former wife, Belinda, opened for business in the mid-1980s—and even before that.

The guest of honor, wearing his ever-present black fishing cap and thick gold chain, sat grinning as Tybee Island Mayor Shirley Sessions bestowed him with a key to the city, thanking him for his 40 years of “unofficial” ambassadorship on behalf of the island and pronouncing the date “Jack Flanigan Day.”

Former WTOC news anchor Sonny Dixon emceed a rowdy roast that revealed a few choice tales, including one from retired Deputy Sheriff Billy Freeman, who years ago pulled Flanigan over for driving under the influence: “When I came up, he was in the passenger seat. He told me the dog was driving!”

Others shared memories over Mai Tais and plates of ribs and deviled crabs to a soundtrack of steel drums provided by Tybee musician mainstays Roy and Martha Swindell. Some talked about when Flanigan was crowned the first Pirate King of Tybee’s annual marauder festival in 2005, others of hanging with him around the restaurant’s poker machines just last week. (My husband, Mark, loves to regale folks about his sweaty summer steaming crabs for Flanigan as a kitchen cook after college in the mid-1990s, before the screened-in hall was built.)

“Man, he has always been just the coolest,” recalled Savannah native Ernie Sims. “I’m in my 70s now, and I was just a kid when I used to see him in the bars. He had such charisma, always keeping an eye on things.”

Those were the days of the Park Lane Lounge, the iconic nightclub Flanigan owned on Abercorn Street in the 1960s, along with several other memorable Savannah hotspots.

“Park Lane was one of the only places a woman could go unescorted and feel safe,” remembered Virginia Ward, who decades later became the Crab Shack’s business manager and still oversees operations.

“It was upscale, the men in suits and ties. Everyone knew everyone.”

Among the many images in the slideshow compiled by Flanigan's daughter, Rachel, flashing on screens at the party was a black-and-white photo of Flanigan from that era: Dark hair in a pompadour, sharkskin suit shining, the aquiline nose and dimpled chin giving more than a passing resemblance to Dean Martin.

“All the girls were nuts about him,” added Ward with a smile.

'Life is good, if you make it that way'

Savannah may be known for being particularly provincial, especially in those years, but when Flanigan arrived as flight mechanic at Hunter Army Airfield in 1953 he knew he’d figure out a way to stay. Born in the desert of Arizona, the military offered a path to see the world, which he did, deploying to Morocco during the Korean War and scoring high enough on I.Q. test to qualify for Mensa.

After his service he found his way into the local liquor business, parlaying those connections into the heyday of 20th-century Savannah nightlife, starting with the Anchorage on Bay Street and adding The Someplace Else Bar, Hard-Hearted Hannah’s and the Park Lane to his portfolio. Between those times and when he transformed the old bait shop on Chimney Creek into a 700-plus seat restaurant, however, there are apparently a few stories that won’t ever be told in full.

Rumors of organized crime in Savannah in the 1970s and '80s have never been corroborated, and the only comment Flanigan might make about characters like “Lou Da Tailor” or “Seldom Seen Levine” would be, “We got along just fine.”

He’ll tell stories about raids on Tybee where island folks loaded up illegal gambling machines on the swing bridge to switch out just as the police came on the island and admits to being aware of a secret casino operation behind a wall in a local men’s room (“crap tables, blackjack, the works”) but he’ll follow up with the caveat, “I don’t know for sure; I wasn’t there.”

Then there is the time he served in an Atlanta federal penitentiary in the mid-1980s. Charged along with his former boss, then-state Labor Commissioner Sam Caldwell with “destruction of a vessel” for the purposes of collecting insurance money, Flanigan was convicted in 1984 and was sentenced to six months' in prison, four-and-a-half years' probation and a $5,000 fine, according to the New York Times.

“I don’t know anything about it,” he’ll say with a shrug. “They couldn’t place me on the boat.”

All of that’s in the past now and in the years since, Flanigan has become far more well known for his expansive hospitality and contributions to the community.

A few days before his nonagenarian birthday, the man everyone calls Captain Jack sat quietly on the upstairs porch of his house on the edge of the Crab Shack property with its view of the marsh cove. A sweet-faced, rescued pit bull mix named Hope sat sentry at the screen door, wearing a gold chain that matched her owner’s and offering her head for pets. Animal welfare has long been a tradition at the Crab Shack, and the captain continues the cause championed by Belinda, who passed away in 2022 at the age of 65.

“I never thought I’d outlive her,” he says wistfully as Hope nuzzles his palm.

Given his penchant for parties and fun, his friends didn’t either, though they admit that even at 90, Capt. Jack appears anything but frail.

“When I first came to celebrate his birthday nineteen years ago, I was afraid to strike up the band because I was afraid I’d give him a heart attack,” laughed musician Quentin “Barabbas” Woodside at last week’s birthday party.

“But he’s still here! He is tough, our Jack!”

Barabbas, as he is known, forged a friendship with Flanigan in Nassau when the captain and Belinda would travel in their charter boat down the Intercoastal Waterway to the Bahamas. That has resulted in several pilgrimages to Tybee a year for Barabbas, notably to perform in the island’s and Savannah’s St. Patrick’s Day parades with his Junkanoo Tribe dance troupe. Several of the troupe’s colorful costumes are on display around the Crab Shack, and Barabbas credits his friend with helping him grow his audience and business.

Capt. Jack sees nothing odd about bringing in Bahamian dancers to help celebrate Savannah’s Irish heritage, a testament to his expansive, ever-adaptive outlook. He continues to dream up new additions to the Crab Shack, and he’s remarkably facile with his iPhone, calling it “his brain.”

“My whole life has been a learning process,” he muses, checking the weather app for any incoming squalls.

When asked what has mattered most to him over the last nine decades, the beloved restaurateur, boat captain, Mensa-level genius, maybe-gambler, and perhaps-pirate becomes thoughtful.

“I’ve met a lot of good people, made a lot of good friends,” he says finally. “Life is good, if you make it that way.”

Jessica Leigh Lebos delivers fresh local content every week at savannahsideways.com. Her latest book, "The Camellia Thief & Other Tales," is available online and at your favorite local independent bookstore.

This article originally appeared on Savannah Morning News: Crab Shack's Capt. Jack Flanigan celebrates 90th birthday