A Look Back… The Shrewd, Persuasive, Colorful Promoter – Capt. Jack DeLysle


If you watch television often enough, sooner or later a news story breaks that is simply crazy or unbelievable, and the person or persons involved in the mayhem always seem to wind up in Florida. As the roaring 1920’s began to sweep across the country, one such character made his way to Southwest Florida, and his name was Captain Jack DeLysle.
He would bring to Fort Myers Beach the Seminole Sands Casino and push for the progress of a bridge; and also had a run in with Sheriff Frank Tippins.

DeLysle on the Beach
According to Karl Grismer’s book, “The Story of Fort Myers,” DeLysle led “an adventurous life.” He served in the British Army during WWI, and arrived in the United States sometime in 1920. Immediately after arriving in Fort Myers, he saw the potential in Estero Island and befriended many of the wealthiest and influential people in Lee County.

In the 1920’s, casinos and hotels began to line what was then known as Crescent Beach. Subdivisions also sprang up offering buyers a piece of paradise. The Sands Casino or DeLysle Casino was described in a letter discovered at the Southwest Florida Historical Society as having “all the accommodations that you could ever want and he [DeLysle] had entertainment from well knowns.” It was known that DeLysle went “all out” for his guests.

A bit further south of his casino, he constructed a 50×65 foot square dancing pavilion. He also established bus service that ran from Fort Myers to the beach every day. The cost was a $1.50 for a round trip pass.

In 1927 he founded the Palm Leaf Publishing Company and published the Palm Leaf newspaper. He purchased a linotype machine from the Tampa Tribune and a secondary machine from the Atlanta Type Foundry, with all the equipment necessary and opened a shop on Hendry Street in Fort Myers.

The Bridge
DeLysle knew in order for his casino to thrive he needed to make access to the beach easier for his patrons. In 1920, he organized the effort to build a wooden swing bridge.

Capt. P. W. Fineran, a civil engineer with the U. S. Army Department came to Fort Myers to inspect the proposed site for the bridge. He was escorted around the area by members of the Crescent Beach Road and Bridge Corporation. Following a tour of the proposed site, Capt. Fineran attended a hearing at the courthouse about the specifications and construction of the bridge.

A permit for the construction of a bridge to cross Matanzas Pass was approved in late October 1920. Work began immediately without any delays. The Fort Myers Tropical News reported, “It is being built of a very substantial material and in a substantial manner, the bridge having the appearance of a railroad trestle.”

It further reported that “The Crescent Beach bridge committee reports that the work is being done in the highest class manner and thoroughly satisfactory.”

The wooden bridge was completed in early 1921. On it’s first day of operation it brought 97 cars to the beach. The toll was fifty cents for up to five people, then ten cents for each additional person. It was reported that during the 1926 hurricane the “bridge was entirely lifted from its piling.” A temporary bridge was used until a “swing” bridge was installed in 1928.

As the bridge came to end of its usage, the Beach Bulletin wrote, “It’s hard to say goodbye to an old friend, especially one who has lent support through wind and rain, borne the load of heavy cargoes, stretched across sometimes troubled waters and provided firm footing for those casting their lines to the sea of plenty.”

The bridge was reduced to a scrap heap as the new bridge spanned over the waters of the Gulf in 1979.

Booze Smuggling
In mid-January 1921, the Tropical News ran the headline “Ship Load Of Smuggled Booze Wrecked In Storm Near Naples.” For Sheriff Frank Tippins, this was just the beginning of a string of moonshiners with whom he’d have a run-in.

When Sheriff Tippins arrived in Naples to investigate, he discovered 320 boxes labeled “Soap” stored on board the schooner “Aurelia,” which wrecked at the mouth of Gordon’s Pass during a northeast gale. The contents inside were bottles of “Country Club” whiskey, and he arrested two brothers — John and Captain Jack DeLysle, who claimed to be a British subject.

The DeLysle brothers were turned over to a federal court in Tampa. During their trial, a diary was discovered that contained information about the smugglers route. The shipment of moonshine came out of New Hope, Kentucky; the DeLysle brothers were picked up at Mobile, Alabama, sailed to St. Andrews Bay, then Tampa, Key West, and Havana, Cuba, before returning to Southwest Florida and getting caught in a gale.

In early February verdict on the DeLysle brothers was reached. According to the local paper, “Capt. Jack DeLysle was declared innocent by the jury and the case against his brother, John, was then dismissed by the court.” One of the deciding factors was that of a witness who claimed to have purchased five cases of liquor from the defendant in Fort Myers. Yet, several other witnesses proved that Capt. DeLysle was not in Fort Myers at the time of the alleged sale.

Bricked Paved Road
In the summer of 1921, with the trial now behind him, Capt. DeLysle had an idea of a brick road leading up to the new drawbridge that spanned Matanzas Pass. His idea was met with “instant favor and prompt response” reported the local paper. He reached out to residents asking for them to pledge a brick for a road that would come off of south McGregor and lead to the bridge and would be made of brick pavers. His campaign, which one person referred to it as the “Wonder Beach Road Fund,” received pledges throughout Lee County, with Capt. DeLysle pledging 50,000 bricks. He also secured three investors to promise 100,000 bricks each, and the private investors also made a promissory note to cover tools, road making machinery, shell and labor costs.

Fundraisers and auctions were quick to follow all up and down Estero Island. But the question of using bricks versus shell or asphalt came into play with residents and town officials. The popular suggestion from residents was to “get a good, smooth road built in the shortest possible time. “ By the time it came to begin work on the road, bricks gave way to an asphalt road.

Over the next few weeks, laborers and engineers constructed and paved a road from McGregor to the bridge. Although it was not Capt. Delysle’s dream of a brick paved road, it was his foresight and spearheaded movement that made it so all citizens and visitors to Fort Myers Beach would have an easier ride there and back.

Casino Fire
Not too long after building his casino, DeLysle lost it to a fire. In the early morning hours of October 2, 1924, fire tore through his establishment and a cottage owned by Dr. V. H. Voorhis. The Fort Myers News Press ran the headline “Fire At Beach Burns Casino and Cottage.” According to the paper, “The origin of the fire is unknown, but people living near say that there were some parties camping near the casino last night and it is thought that embers from their campfire blew on the cottages, setting them afire.”

Both the casino and the cottage were “consumed.”

There was no mention that he rebuilt, but the letter from the historical society stated that during the hurricane of 1926 the casino was “washed away, very little left to realize there had been a building at that place.”

DeLysle & Mathews
It has been recorded that DeLysle traveled to the United States with his “beautiful wife who aided him in making friends.” Her name was May Winifred DeLysle.

He would marry a second time on September 28, 1926, to Elsie Marie Mathews in Enfield, Halifax County, North Carolina. Accompanying him was Ronald Halgrim, a staff member of DeLysle’s newspaper, Palm Leaf. According to the Fort Myers News Press, “they were married in a beautiful church wedding ceremony at the Baptist church.”
After a brief honeymoon in Philadelphia, they drove back down to Fort Myers and resided in Lovejoy Park.

Two years later they welcomed their daughter, Jacqueline into the world. The couple divorced and Elsie, along with their daughter moved to North Carolina to be with Elsie’s parents. She took a job as a bookkeeper.

Although described by many as a “shrewd, persuasive and colorful promoter,” according to Grismer’s book, DeLysle certainly brought entertainment and tourists to Estero Island and was a leader in developing the beach.

T.M. Jacobs

Southwest Florida historian T. M. Jacobs serves as an advisor to the Southwest Florida Historical Society and is a regular contributor of articles about early life on the beach.