The Ghost of Al Capone's Mistress

By M.P. Pellicer | Stranger Than Fiction Stories
​Capone had many mistresses, but some held his interest longer than others. One of these allegedly was Mary Ann Brown, who also went by the name of Vera. She is a mysterious woman, because very little is known about her, if she ever existed at all.

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Al Capone used several aliases, one of the earliest was Al Brown c.1931

Perhaps she used the surname of Brown in imitation of Capone's alias Al Brown, which he used since 1920 when he was the keeper of the Four Deuces saloon at 2222 S. Wabash Avenue. Later in life, he would be known as Scarface.

When or where they met is unknown, but chances are that by the time he bought his Miami house in 1927, they were involved. He paid $40,000 for the 10,000-square-foot Mediterranean Revival estate, and spent $200,000 in improvements.

The property was built in 1922 by Clarence Busch, the beer magnate, who left several Anheuser-Busch emblems around the house. It was once featured as having the city's largest private swimming pool.

Capone made it his family home, and he brought his wife, son, and brothers to live there. He bought the property under his wife's name.
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By comparison, he bought Vera a modest, newly built, stucco-and-wood bungalow measuring just over 1,000 square feet. She lived there with her two daughters, Mary and Ann, both allegedly fathered by Capone. No doubt the property's appeal lay in the fact that in those years, Port Orange, a small town covering only 29 square miles, was in a remote part of Florida. The house was a stone's throw from the Halifax River. It was the perfect setting for transporting illegal hooch brought in by rum runners who loaded up in the Bahamas and came in under the cover of night.

There is no known picture of this mystery woman, only a rumor that she was French and probably had changed her hair color to blonde, which Capone expected from all his girlfriends.

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Port Orange house supposedly haunted by Capone's mistress c.early 2000s

So how do we know this woman existed? In 2005, Christopher J. Rollier who once lived in the Port Orange house wrote House of Shadows: The Mistress of Al Capone, which detailed his experiences once he bought the property in 1996, and started renovations. He lived there for 10 years.

​According to Rollier the place was not only haunted by Vera, but by her bodyguard. He would even go on to blame the ghosts for the divorce from his wife.

More than likely though the man left behind was not a bodyguard, but a mafioso left to guard illegal hooch secreted at the house.

​He described it this way:

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I didn't know it was (Capone's mistress) until I described her down to the bun on her head. But the bodyguard made me skittish, especially when I was living by myself. I felt he caused us to break up. She (Rollier's wife) was scared living there. But I never feared for my own life.

Old-timers started telling me of a local banker at the time who laundered money in a house across the street. There was also a house in Capone’s mother’s name in New Smyrna Beach, where he’d go.

Mae Couglin who became Mrs. Capone in 1918.

Rollier said he had a photograph of her in a neighbor's trunk. Eventually, he brought a paranormal team to investigate, who told him the identity of the ghosts was Capone's mistress and their daughters.

The local historical society has no record of Capone being in the area, but considering he was conducting illegal business plus visiting his favorite moll, it's understandable he would have kept a low profile. However, unofficial sources tell of Capone's visit to Ponce de Leon Inlet, and going south on the Halifax River heading to Miami.

Surprisingly, for being more of an urban myth than reality, this story of Al Capone's mistress just won't go away. ​

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There is another version, where Capone was rumored to keep his mistress and illegal liquor at an old brick house along the Gabordy Canal, located at 1802 S. Riverside Drive, New Smyrna Beach. The 2-story brick house dates back to 1926, and like the other property in Port Orange, it has access to the Halifax River. The backyard of the property on the south side has a concrete dock. It also has an unusual feature for Florida homes, which is a full basement accessed from the kitchen or the exterior screened porch.

The property's notoriety is linked to being a stash house for bootleg liquor, rather than a romantic hideaway. It's said this is where those who worked for the mobster played card games and took a rest, before heading north with the hooch. Perhaps Capone's mistress acted more as a ruse to explain his visits to the area than anything else.

In 1920, New Smyrna's population was only a scant 2,500, and the property appraiser's office had no records predating 1955, so there is no way to know who occupied the property about 100 years ago. The local historical society has only heard that it was bought by a lady from Chicago, who might have been Capone's mother. It was a solitary home built out in the middle of nowhere.

Another persistent rumor tied to the house is the existence of a tunnel system that stretched to the canal, and was used by Capone and others to enter the house unseen. The owner of the property in 2018 was told the tunnel had to be filled in a long time before because it was caving in; there has never been concrete evidence of this.

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As late as 1955 moonshine stills were being raided along Central Florida's east coast.

Jeff Hostetler who owns a local painting system said he heard rumors the house was bought in Capone's housekeeper's name, in an effort to keep law enforcement from knowing the gangster was operating in the area.

In 1974, there was a mysterious death in the house, where a local woman  was found dead in bed by her husband. She had reportedly been drinking heavily for the past several years and had been taking Valium, however her pharmacists told police he thought it unlikely an overdose or a mixture of the tranquilizer and alcohol could have caused her death. Foul play was not suspected, however police were unsure if it was a suicide or an accidental death. Her husband a retired engineer, 25 years her senior, followed her to the grave the following year.

The house was last sold in 2021.

Capone seemed to have liked Florida, and there are rumors tying him to Mount Plymouth Hotel and Country Club in Lake County, and that he bought a house for his mother in St. Petersburg. Another place it's said he frequented was the Indian River Lodge, a three story inn which also boasted a basement. It once stood at South Riverside Drive, six blocks from the house on Gabordy canal.

​During those years, liquor stills kept producing moonshine from the small islands close to Mosquito Lagoon, in addition to what was being off-loaded from rum-runners.

​In 1955, long after Prohibition was repealed a giant still 45 miles southeast of Sebring was raided. Authorities seized 405 gallons of moonshine, along with 6,525 gallons of mash ready for distilling.

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Al Capone used his Palm Island estate as a getaway from his life as a big time Chicago gangster. He died in a small bedroom facing the driveway

As obscure as the stories of Capone's mistress are, his presence in South Florida left an indelible mark.

During the early 1920's, tourism in Miami flourished, especially for those fleeing the cold winters up north. However, Dade County had gone dry a full six years before the Volstead Act was passed in 1919, and bootlegging was a thriving business. Selling liquor to what was known as blind tigers or speakeasies had brought organized crime to Miami, and it's little wonder Capone made a home there.

​Then the Hurricane of 1926 roared into Miami, and put the area into an economic downspin three years before the Great Depression hit the rest of the country's economy.

​Drawing others to take the heat for him was a regular M.O. for Capone. In the winter of 1926-27, he met Parker Henderson Jr., who ran the Ponce de Leon Hotel. He was also the son of Miami’s mayor.

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J. Fritz Gordon, Al Capone, and Mayor of Havana, Julio Morales, Havana, Cuba, c.1930

​Henderson, who was a gangster groupie, helped Capone buy the mansion on Palm Island. He did this by working with Newt Lummus Jr., the Mayor of Miami Beach. He also helped Capone acquire guns and cash checks. In exchange, he got a belt buckle that Capone handed out to his friends that cost about $275. Unfortunately for Henderson, he became known as an associate of Capone.

In 1927, Henderson was questioned in the murder of Frankie Yale. Yale was killed in retribution for the murder of Tony Lombardo, who ruled the Unione Siciliana in Chicago. Two pistols thrown away by the killers were traced back to Henderson. He told investigators he had gotten them for Capone. Lucky for Henderson, he was in North Carolina when the crime was committed, which is why he was only interrogated in the matter.

In 1930, Miami Police arrested Al Capone's brothers, John and Albert, along with four other men, after a raid was conducted and liquor was seized. The city fathers were not happy that Capone lived in Miami and would harass him and his cronies in any way they could.

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Al Capone's funeral at his Chicago home on Prairie Ave c.1947

Capone's unwelcomed stay in Miami was short-lived when he was arrested in 1931 for tax evasion and sentenced to 11 years.

In May 1932, he arrived at the Atlanta U.S. Penitentiary, where he was officially diagnosed with gonorrhea and syphilis. He also had a perforated nasal septum due to his use of cocaine. Without a steady supply, he suffered withdrawal. His mental acuity declined markedly, and Red Rudensky, a small-time hood, became his protector from jailhouse bullying.

In August 1934, Capone was sent to the recently opened Alcatraz Federal Penitentiary. Two years later, he was stabbed by inmate James C. Lucas.
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It was hard to recognize the man who was known for his custom suits, costly cigars, gourmet food, and numerous romantic liaisons, as well as being the mastermind behind the 1929 Saint Valentine's Day massacre carried out while he was at his Miami home. Seven members of the rival George "Bugs" Moran mob were machine-gunned to death while lined up against a garage wall in Chicago’s Lincoln Park neighborhood. This was Capone's style, which was to order other men to do his dirty work. The slaughter led to the federal government stepping in to investigate the gangsters running Chicago.

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93 Palm Island, Capone's home until his death. c.1967

After Capone's death, his wife, Mae, continued living at their house on Palm Island until 1952, when she sold it. The house, though, could never outrun the reputation of its most famous owner.

It's not coincidental that Capone chose Palm Island as his Florida home. It was right down the street from the Palm Island Club. It was a snoots-only casino opened in 1922 by Ed Ballard, co-owner of the French Lick Casino. It admitted only tourists, the rationale being that if non-locals got fleeced, police would look the other way. Along with the gambling, illegal liquor flowed, as well as all the vices found in a speakeasy were allowed within its walls.

The club was taken over by Big Bill Dwyer, a New York bootlegger and owner of the racetrack Tropical Park. They offered a show which featured a naked showgirl in a huge glass of champagne. In 1939, it was renamed to the Latin Quarter and was taken over by Lou Walters, the father of Barbara Walters.

Other well-known gangsters visited the Palm Island Casino and stayed at Capone's mansion. There was one story associated with Lucky Luciano that was described as:

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One woman closely associated with Luciano was Gay Orlova—the stage name of a twenty-year-old chorus girl in a Broadway show. Luciano, reputedly, fell head over heels for her. Born in Russia, she had left with her family during the revolution. Luciano met her in 1934 after she performed in a show at the Palm Island Casino in Florida. He was staying with Al Capone’s brother, Ralph, in his mansion. After that first meeting, they were smitten with each other and were seen around town together. Lee Mortimer, a gossip columnist, asked her what she saw in Luciano.
    'How can you go for that gorilla?' he said.
    'I love Charlie because he is so sinister,' she replied.

Capone's Palm Island mansion c.1995

In 1953, Nat Ratner, a developer, offered new homes on the island, but declared it was the end of "the gangster curse" on Palm Island. What that curse was has never been fully explained.

A scant three years after Mae Capone sold the house, it was up for sale again for only $72,500, which was much less than it was worth.

​In 1959, it was being rented out as a movie location.

In 1961, Harry Renkert, the owner of the house, had his boat explode by the dock in front of the property. He had rebuilt the whole boat from an old hull, and hadn't used it for several weeks, and the mishap was blamed on a buildup of gases.

In 1967, the property was up for sale again by the current owner, Dr. James Chimerakis, furnished or unfurnished at a "liquidating price" and referred to in the ad as the "Al Capone Estate".

In 1971, it was up for sale again, "as is" for only $60,000.

In 1979, Maharaj Ji, "God on Earth" of the Divine Light Mission, rented the place for $8,800 a month.

In 1984, it was owned by Hank and Rose Morrison, who described a "strange vibe in the house". They said an adjacent property, 10 Palm Island, was also being secretly owned by Capone, and like other Capone properties, there was a rumor of "secret passageways and concealed rooms."

Capone's Miami home eventually fell into disrepair until it was bought by investors in 2015 and renovated with modern amenities. It was purchased in 2021 for $15.5 million, and unexpectedly, in August 2023, the property was demolished, much to the dismay of local preservationists. As of March 2026, the property is on the market for $23.5 million.

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Capone's house in Chicago c.1929

Capone’s original home at 7244 South Prairie Ave., Chicago, was originally built in 1908 and purchased by the mafia boss in 1923. Capone lived there until he bought his Miami home, after which he let his mother, Theresa Capone, live there.

Salvatore "Frank" Capone's funeral was held there. He was Al Capone's older brother, who was killed in 1924 by police officers, Phillip J. McGlynn and Lyle Grogan, near a polling place in Cicero, Illinois. He had been intimidating voters opposed to the ticket backed by the Torrio-Capone mob. All the brothels and gambling joints in Cicero closed down for a couple of hours in tribute to the gangster's death.

Theresa died in the home in 1952; it was then sold to William B. Petty. It was last up for sale in 2016.

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Two Gun Hart a.k.a. James Capone

The question is, do Al Capone or any of the important women in his life haunt the homes where he lived or used to carry on illegal activities? And as to forks in the road, some are more important than others.

Case in point, Al Capone had an older brother named James Vincenzo Capone, who was the oldest of 9 children born to Gabriele and Teresa Capone. He ran away from home at age 16 and joined a circus, and after WWI, he legally changed his name to Richard James Hart. He moved to Homer, Nebraska, and became a federal prohibition agent and sharpshooter. He got the nickname of "Two-Gun" Hart after successfully raiding bootleggers. 

In 1926, Hart became a special agent of the Bureau of Indian Affairs assigned to the Cheyenne River Indian reservation in South Dakota. He was tasked with protecting President Calvin Coolidge when he visited the Black Hills. Later, he worked at the Spokane Indian Reservation. He was credited with arresting more than 20 wanted killers in that area, destroying countless stills, and arresting moonshiners. He also worked as a law enforcement officer on the Coeur d'Alene Reservation in Idaho. He would go on to become a marshal and justice of the peace. 

Hart married Kathleen Winch in 1919, and they had four sons. She never learned his real surname till 30 years later, three years before he died in 1952.

Their son Richard Hart died in 1945 while serving during WWII. He was buried in Manila and awarded the Purple Heart.

James Vincenzo Capone became known as Al Capone's "white sheep" brother.

Source - ​The Orlando Sentinel, The Miami Herald, The Tampa Tribune

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