In ‘Sunshine State Mafia,’ meet Harlan Blackburn, Orlando’s real-life mobster king

ORLANDO, Fla. – Before there was the Florida Lottery, there was Bolita.

Like the Lotto, people bet on numbers on a ball, and if their number comes up, they win money.

Like the Lotto, Bolita was extremely lucrative – a multi-million-dollar industry.

Unlike the Lotto, Bolita was illegal, managed by the Mafia.

And in Orlando, the king of Bolita was Harlan “The Colonel” Blackburn.

In the book “Sunshine State Mafia,” by Doug Kelly, which comes out March 5, Blackburn merits his own chapter, alongside Florida mob legends like Al Capone and Meyer Lansky and Santo Trafficante Jr., head of Florida’s own Mafia family based out of Tampa.

There were gangs in Central Florida before Blackburn. The Dixie Mafia, or the Cracker Mob, out of Mississippi, loosely ran organized crime in the area, including moonshining and bootlegging, even after prohibition because there were still dry counties.

“There was a lot of extortion,” Kelly told News 6. “There were a lot of burglaries, there was a lot of fencing of goods that they were they were doing. So that was going on, but nothing like it became later. Nothing like when Blackburn got into it, headed it and turned it into really a quasi-mafia organization because he had lieutenants and people on the street, dozens and dozens of people collecting money.”

$100,000 to $200,000 a week

Blackburn, an Orlando resident born in 1919, came up through the Dixie Mafia, and Kelly says he was a good wage earner. But like any classic Mafia story, Blackburn got control of the Central Florida operation when his boss, Ed Milam, turned up dead in a ditch south of Kissimmee in 1953.

At first glance from photos, Blackburn appeared to be a pleasant enough Southern man. He was described in historic newspaper clippings as a “good old boy.”

“He… looks like somebody you would see anywhere out in public and just wouldn’t look twice. There’s some mobsters who look scary, you know, but not him. He looked like the everyday man,” Kelly said.

But Blackburn ruled with fear. He had enforcers who made sure that he was getting the money he expected.

“If they didn’t make their payments, he would send someone down — not him,” Kelly said. “He’d send someone down with a baseball bat and break the person’s leg. So people knew this was happening. They knew that while The Colonel wasn’t the guy with the bat, he ordered it. So he was treated very gingerly with respect.”

It helped that he had the blessing of the Trafficante Family in Tampa. But the popularity of Bolita in the 1950s and 1960s also helped. People could bet on a numbered ball for 50 cents and come away with $50 or $100, Kelly said. The balls were numbered up to 52 and placed in a bag and then a number would be pulled. Drawings happened almost daily. It was popular with the poor and with Cuban immigrants.

In Harlan Blackburn’s Orlando, you could get a game of Bolita anywhere – in the neighborhoods, in garages, at gas stations, in Five and Dime stores.

“They would actually do it right out of their stores. It was so flagrant. They could just walk down the street practically with a sign and say get your tickets here,” Kelly said.

Bolita was so popular that Blackburn’s operation was pulling $100,000 to $200,000 a week in income. Blackburn’s territory stretched from Polk County up north through metro Orlando and then west into Pasco and Citrus counties. Kelly said Blackburn would end up in jail now and then for illegal gambling, but he always got out, and his operation kept going even while he was behind bars.

“There just wasn’t that big a police force or law enforcement. And there were no detectives really, they weren’t concentrating on that,” Kelly said. “They just worried about the major crimes of murder, arson, those types of things, assault and batteries. And they really considered that not. They just looked the other way.”

Kelly said cops on the beat were also easy to corrupt – they made little money, and the extra cash from Blackburn was enticing. Kelly said Blackburn bribed judges and politicians too.

“They contributed heavily to the campaigns of people. The mayor of the cities and the council members or commission members. All they needed was a majority, you didn’t have to corrupt everybody,” Kelly said.

RICO changes the game

But the good times started to end in the 70s, not just for Blackburn but for organized crime everywhere, all thanks to the Racketeer Influenced and Corrupt Organizations Act (RICO). Blackburn’s case was one of the first RICO cases in Florida.

RICO allowed prosecutors to try racketeering cases against organized crime leaders because they could build a case based on patterns of behavior.

Blackburn got a 22-year sentence in federal prison for gambling and tax evasion. Then in 1975, three years into the sentence, he was paroled and turned over to state authorities after he was convicted of ordering an assassination attempt on his lieutenant, Clyde Lee.

“He set up that he would be in a phone booth, and he was going to call (Lee who was in) another phone booth,” Kelly said. “A car went by that phone booth… and pull right up and just emptied his pistol. Four bullets hit him. He lived.”

But Blackburn had tried to give himself an alibi by setting up another car to pull up to the phone booth he was in and shoot at him. Kelly says a milk truck got in the way.

“The jury did not believe he didn’t plan that. So he did time for that,” Kelly said.

By the time he got out of prison, Bolita was dying and the Trafficantes, who had supported him, were heavily into drugs. Kelly says Blackburn started drug dealing too, in between stints in prison as investigations finally caught up with him.

Then in 1992, Blackburn was charged with selling drugs out of his home in Seminole County. He got a 24-year federal prison sentence.

Central Florida’s former mob king died in a prison hospital in Minnesota in 1998.

A beginner’s guide to Florida’s history with organized crime

Blackburn’s story is just one part of “Sunshine State Mafia.” Kelly’s book is a quick and entertaining read for people who want a beginner’s guide to Florida’s history with organized crime. His stories range from storied Mafia leaders (like Al Capone), to only-in-Florida-style stories of colorful characters and whole communities that tangled with crime for a taste of the good life.

In one story, Kelly tells of Everglades City, a poor fishing village in South Florida where drug dealers paid residents to take in packages for them. Investigators realized something was up when rundown trailers were suddenly replaced with luxury homes.

“Whole families were taking part,” Kelly said. “And these people were dirt poor. And all of a sudden, they have Cadillacs and yachts there. There’s a shabby trailer that turns into a six-bedroom home on the water. They were stupid. I mean, it was going on for years. Yeah, years, and all of a sudden they just couldn’t help themselves.”

The book at times also turns into a memoir as Kelly, a freelance writer who was also a private investigator and a security consultant, relates his own close encounters with mobsters and people with mobster ties – like checking Frank Sinatra’s home for listening devices, or mobsters calling him up to complain about a fishing article he wrote.

“That’s what brought me into touch with the organized crime situation being based in Miami in the 80s,” Kelly said. “So I became exposed, if you will, to all kinds of different characters. Most of them, of course lawful, but a few of them who were bad apples.”

Kelly also talks about the state of organized crime in Florida today, who replaced the mobsters of old and what they are up to, and how law enforcement is better able to take them down now more than ever.

“Statistics are showing that because of the greater existence of law enforcement cooperations with the state and the FBI, and the Drug Enforcement Administration and all these different groups, organized crime stats are dropping,” Kelly said. “They are biting into the free-for-all they had 30-40-50 years ago. It’s not the same. It’s harder to get away with something now, because law enforcement is a lot more sophisticated and a lot more prevalent.”

“Sunshine State Mafia: A History of Florida’s Mobsters, Hit Men, and Wise Guys” comes out on March 5 from University of Florida Press. It’s available for pre-order now where books are sold.

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