When I pull up to the iconic Crab Shack on Tybee Island for Captain Jack Flanigan’s 90th birthday party on August 8, I think of the phrase “This is how legends are made,” because it also happens to be the 40th anniversary of the place where “the elite eat in the bare feet”.

When I got an invite from Captain Jack’s granddaughter Rachel Flanigan, I originally had prior plans, but the more I thought about it, I knew I had to change them because I knew everyone from Chatham County Sheriff John Wilcher and his former right hand man, Billy Freeman, to Olympia Cafe’s Vasilis Varlagas, and the legendary Stratton Leopold would grace us with their presence.

Seriously, the first person to join me and Captain Jack in his second floor sunroom overlooking Chimney Creek is Stratton. The famous storyteller takes a seat with me to listen to the Captain tell a few tales. “I was in Atlanta when I saw an ad in the paper for a marina on the Georgia Coast. I moved back down to Savannah, got my Captain’s license and started charter boat offshore fishing. We would bring in our haul and cook what we caught.”

“When I moved back to Savannah after a detour to Atlanta, 40 plus years ago, there was a different set of people. It was more about the water and the children. There were fishing tournaments, and once-a-year during Thanksgiving, fathers and sons would camp on Little Tybee for a week.”

When I ask what the original building looked like back then, Captain Jack leans over, grabs a framed 8 x 10 pic and hands it to me. “It was a concrete block building, and was maybe 12 x 24 feet. It is now the gift shop and aviary.” Then I ask how big the Crab Shack is now. “We are sitting on four acres and can serve over 700 at one time.”

Making our way downstairs, we are immediately bombarded with greetings, hugs and gifts by everyone from former Chatham County Manager Russ Abolt, the former first lady of Georgia Shirley Miller, and famous judge Steve Scheer.

Inside the Party Shack, I am making a lap past the Leopold’s ice cream cart, and stations filled with bacon-wrapped scallops, a beef round, and their signature deviled crab medallions, boiled shrimp and all the fixin’s, when I hear a familiar voice call my name. Say hey to Virginia Ward, the 26 year lady of the Shack, with the official title of Business Operations Manager, and long-time friend of the Captain.

“I met Captain Jack in 1963 when he was the owner of The Park Lane Lounge on Abercorn near 44nd St. I lived in an apartment two doors down. He was very charismatic and quite the ladies’ man,” shares Virginia. Some things never change!

Speaking of ladies, I see Diane Rousakis Biggs and her mother Kitty Cobb Elliot, who is celebrating her 91st birthday in November. The Savannah High grad is absolutely gorgeous, and has high praise for the Captain when she declares that he is “living legend.”

Another fascinating female is Tybee Island royalty Charissa Murray. The talented artist grew up on Tybee, knows everything and everyone on the island and produces events like the Pirate Festival and Tybee Tour de Art. When asked what her talents are, she laughs and responds “I drink well with others!”

After proclaiming that the Crab Shack peeps are her family, Charissa poses with hotel kings Dillion and Akash Patel, then I move over to hug musician Roy Swindelle, long last-seen Sonny Dixon and the Mayor of Tybee Island, Shirley Sessions with her sister Sandy McCloud. 

Of course the sisters can be convinced into singing a personalized “Happy Birthday” montage for Captain Jack as they ease their way over to hug on WSAV’s evening anchor Ben Senger. The wickedly funny TV dude tells me, “I am amped to get to highlight the personalities and the businesses that make this community so dynamic. Captain Jack is my first feature segment.”

Arriving next are close friends, franchise consultant Greg Lard, Savannah Smiles’ Tripp Morales, and The Islander’s Rudy Shirah. I  wish Rudy would tell us some stories from back in the day, but I know how loyal barkeeps are with their secrets.

By now I am hot–like steaming hot–so I take a seat at the bar where two monster fans attempt to cool me and the vivacious Barbara Young of Tybee Turtles Transit. Joining us is my assistant Kaitlin Sells who takes over photo duties so I can chat with people like Olympia Cafe’s Betsy and Vasilis Varlagas.

Animated about his love for the Captain, Vasilas tells me, “Jack came into my restaurant to deliver a personal invitation. I have known him for 33 years and am honored to call him a good man” shares the former professional soccer player. “I was 18 years old and played soccer for four years, have owned Olympia Cafe for 34 years and have been married for 38 years,” adds the Thessaly, Greece native.

With a room full of family and longtime friends, Sonny Dixon starts the roast (or should I say toast) for Captain Jack. After the mayor presents Jack with the key to the city, and proclaims August 8 as Jack Flanigan Day on Tybee, I take a seat to hear story after story from his longtime friends. 

As I glance around the room, I see people of every age sharing a night where we honor our local living legend. As much as they (or I) may know about Captain Jack, I think Virginia may have said it best when she wrote about him in the “Tybee Beachcomber” five years ago.

“He’s a card-carrying Mensa Member, a yellow-dog Democrat, twice married, twice divorced, and has one son, three grandchildren and two great grandchildren. He spent a little time ‘away’ (for which Judges & Federal Agents hold him in high esteem, because he could have saved himself at others’ expense, which he would not do). He makes no apologies for anything he has done, has few regrets and is a friend to us all, ” shared his long time friend.

From life on a Navajo Indian Reservation, spending his teenage years in New York, and serving in the Air Force during the Korean War, to owning iconic bars–and now–40 years at the Crab Shack, Captain Jack is sometimes the bad boy that you can’t help but love. 

With his signature Greek fisherman’s cap, sunglasses and colorful party shirt, he is a lot like many of the movie stars that have graced his doors. He has been the star of his own movie here and, like Frank Sinatra, he has done it “My Way.” I am proud to be one of his chosen friends to celebrate a life well lived!

This article appears in Connect Savannah | August, 2023.