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Thursday, December 29, 2016


Black Sheep and Prohibition in Key West
Every family has its black sheep. Mine was no exception. My grandfather was a well-known lawman in North Jersey back in the first half of the twentieth century. He was responsible for bringing many gangsters to justice. You might even recognize some of their names. But much to his embarrassment, one of his brothers was a bootlegger in Atlantic City during Prohibition. This great-uncle of mine was such a persona non grata in our family that I’m not even sure of his first name.

You may have watched Boardwalk Empire on HBO a few years ago. The character of Nucky Thompson, played by Steve Buscemi, was based on the real life of South Jersey crime boss Nucky Johnson. Since Nucky Johnson controlled all the bootlegging in and out of Atlantic City, I suspect Great-Uncle Black Sheep was one of his henchmen.

Because of my family history, I was fascinated by some history I stumbled upon during a trip to Key West. With the extension of the Florida East Coast railroad, tourists didn’t have to travel to Havana during Prohibition in order to drink. They could winter in Key West and avail themselves of the many illicit bars that dotted Duval Street and other parts of Monroe County, thanks to the rumrunners who routinely traveled the ninety miles between Cuba and Key West. Although they needed to stay vigilant to avoid capture by Prohibition agents, the Key West rumrunners knew local law-enforcement would look the other way.

One such rumrunner was Raul Vasquez who not only imported large quantities of Cuban liquor, he ran a “club” at 1117 Duval Street. Most businesses advertise to attract customers, but when you’re running an illegal business, you can’t take out ads in the local newspaper or put up billboards. Most operators would post a small notice reading “club in rear.” However, Raul came up with a rather ingenious way of promoting his drinking and gambling establishment without violating the law.

Many old frame structures in Key West were decorated with Victorian style gingerbread, especially enclosing porches and bordering outside staircases. Instead of the traditional gingerbread motifs carved into the spindles and railings, Raul commissioned decorative gingerbread depicting bottles as well as hearts, spades, diamonds, and clubs to advertise that liquor and gambling were available at his establishment.

Today Raul’s old speakeasy is a bed and breakfast, but part of its Prohibition history can still be seen in those upper story porch railings.

I’ve plumbed the depths of my family history to come up with plots for many of my mysteries and romantic suspense books. After learning about Raul, I have to wonder if he and Great-Uncle Black Sheep ever crossed paths. Did my bootlegging ancestor travel back and forth to Cuba from Key West? If so, did he occasionally imbibed at Raul's speakeasy?

I just may have to send Anastasia or Gracie to Key West in a future book to find out.

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Dr. Mary Kennedy said...

This is a fascinating bit of history, Lois! I had no idea about the Cuban connection, the "clues" in the gingerbread motif etc. I really need to get back to KW!

Lois Winston said...

Mary, what I discovered was that if you steer clear of the tourist traps in Key West, you find a treasure trove of out-of-the-way gems. The Key West Cemetery is fascinating if you're a history buff. We spent several hours walking around that.

Angela Adams said...

Wow! Interesting...

Lois Winston said...

Thanks, Angela!

Sharon Ervin said...

Enjoyable and worth the couple of minutes it took to read. Thanks,

Lois Winston said...

Thank you, Sharon!

Pat Marinelli said...

Interesting time.

My late Dad (he was 17 at time and had his captain license) was asked to bring a sail boat from College Point, NY to Jersey (Woodbridge, Perth Amboy area) by his friend's father. The two kids had the boat shot out from under them by the Coast Guard. Unknown until then they were running booze for the other kid's father. He figured the kids were under aged so they wouldn't get arrested. I remember the story because I went to school with the guy's daughter who was to get the load of booze which is why Dad told me the story. The world is a small place.

Lois Winston said...

Fascinating, Pat! Thanks for posting.

Anne Carrole said...

That was so interesting Lois! Thanks for sharing.

Lois Winston said...

Glad you enjoyed it, Anne. Thanks for stopping by.