When Tampa was a hotbed of organized crime from the late 1800s through mid 1900s, the Hillsborough County Sheriff’s Office charged the Vice Squad with cleaning up what the federal government deemed one of the most corrupt cities in the nation. The Tampa Bay Times has obtained a cache of Vice Squad reports from the 1950s and 1960s, which offer insight into their investigations and what they were up against.
TAMPA — She wore flowery dresses, owned a mom and pop business, called her ex-husband “Papa Joe,” and kept a Bible in her purse.
Dorothy Puleo seemed more like a soccer mom than someone involved in a criminal enterprise.
But in the 1950s and 1960s, when the illegal lottery was as much a part of Tampa as cigars and Cuban sandwiches, those working for an organized crime syndicate came from all walks of life — age, ethnicity, career and gender.
The role of women in organized crime is usually stereotypical in movies, they are portrayed as stay-at-home wives or girlfriends who look the other way as the men break the law.
The story of Dorothy Puleo, told through newspaper archives and a Vice Squad report, shows that women sometimes had active roles.
Her tale begins in February 1962, when the Vice Squad raided Dorothy Puleo’s business, Maryland Ave. Grocery, on a tip that numbers were being sold there.
“Tucked inside the woman’s purse,” the Tampa Tribune reported, a “was a wad of about 50 bond tickets” and a Bible hiding another 29.
Bond was an illegal lottery based on the stock market. Gamblers chose three numbers from 1 through 100.
The winning numbers were then “taken from the daily closing sales of the two New York stock exchanges and bond list,” the Tampa Times explained in April 1960, “by taking the fifth digit from the right on each of the three closing sales figures.”
But none of the tickets were hers, Dorothy Puleo, 40 at the time, told the deputies. Her ex-husband, “Papa Joe,” put them there.
Joe Puleo, 52 at the time and not at the store, was later arrested. Both Puleos were charged with operating an illegal lottery out of the grocery store.
That was not abnormal.
Newspapers stories from 1962 detail similar businesses being involved in the illegal lotteries. S&M Grocery, Stepp-Inn Grocery, Green House Cafe, Manny’s Cigar Store and Urso’s Fish Market were among the them. The arrested included owners and employees of different sexes, ethnicities and ages.
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None of those individuals were in charge of the criminal operation. They sold numbers and collected the wagers for a larger syndicate.
S&M Grocery was raided around the same time as Maryland Ave. Grocery and was also owned by a woman, D.G. Figuerdo. She, too, was charged with operating an illegal lottery.
Women had other roles, too, according to the late Susan Rivera, whose late husband Johnny “Scarface” Rivera ran numbers before they met.
She shared stories with the Tampa Bay Times in 2010.
A woman Rivera referred to as “Jitterbug” sold bolita from a grocery store and picked up bets from other businesses that she then delivered to a drop house, where the wagers were recorded by the umbrella syndicate.
To remain off law enforcement radar, she would taxi neighborhood kids to wherever they needed to be, creating the illusion that she was an active mother. She delivered the bets after the kids were dropped off.
Other woman who delivered bets, Rivera said, hid the evidence in their underwear.
The tickets found at Maryland Ave. Grocery were receipts of bets that were later picked up and delivered to a drop house.
Which syndicate did the Puleos work?
After the February 1962 arrest, Joe Puleo offered to “make a deal,” according to the Vice Squad report. He and his ex-wife would “turn up quite a few big shots” if the Vice Squad would get them “out of the trouble they were in.”
The Vice Squad and the assistant state attorney offered immunity “if he would give us information in regard to the higher-ups,” says the report written by the Vice Squad’s Kenneth Henning, but “this writer did not hear from Mr. Puleo from that day on.”
So, the Vice Squad returned to Maryland Ave. Grocery in June 1962 and, in a trash can, found torn up tickets for bolita, a game that typically based the three winning numbers on the Cuban lottery or pulled the winning digits from a sack filled with balls numbered 1 through 100.
Dorothy Puleo again claimed innocence, telling the deputies that they were misinformed. Those were grocery receipts, she said.
She was again charged with conducting an illegal lottery, but maintained the same defense during her court hearing in July. And she brought a witness.
Henry Kemp, 40 at the time, testified that one of the slips of paper that the deputies said was an illegal lottery ticket was his grocery receipt.
“Knowing that the ticket found at the store was a bolita ticket and nothing else,” says the report, a Vice Squad deputy waited for Kemp “to emerge from the courthouse so we could place him under arrest for possession of bolita.”
Dorothy Puleo’s attorney protested the arrest, telling the deputy that his client, Kemp, had a “right to counsel,” according to the report. But Kemp denied that he had an attorney and said he had never seen that lawyer “until they were in court that morning.”
Kemp changed his story during questioning.
He did know the attorney and was at his office with the Puleos just prior to appearing in court.
“He also stated that Mr. Puelo and Mrs. Puleo had gotten into an argument in the attorney’s office” says the report, with Joe Puleo demanding that his ex-wife stop messing around with bolita.
Kemp then admitted that he played bolita through Maryland Ave. Grocery and agreed to let the Vice Squad search his home, where they found illegal lottery tickets with numbers matching some of those taken from the store. Joe Puleo paid Kemp’s $1,500 bail.
The Times was unable to learn the outcome of Kemp’s arrest.
Joe Puleo was sentenced to pay a $100 fine.
Dorothy Puleo had her grocery store’s liquor license revoked for two years.
“If they’re going to be in the bolita business, they have no business being in the liquor business,” the Tampa Tribune quoted the State Beverage Department director as saying at a hearing.
The director then addressed Dorothy Puleo. “Do you know that every time you buy bolita you put money into the pockets of gangsters here?”
Dorothy Puleo responded, “Yes.”
News archives do not report on her being arrested again.