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The Cigar Runner
The Cigar Runner
Over a decade ago, Richard “Mick” Connors was stopped crossing the Ambassador Bridge from Windsor, Ontario into Detroit. After confiscating the few thousand cigars on his person, U.S. Customs assumed they had seen the last of him. They were wrong. At last, Connors breaks his silence.

“Don’t look up!” the cop yelled. Hands cuffed behind him, a handgun pointed squarely at his head, Mick Connors was only happy to oblige. If nothing else, it would give the Chicago lawyer some time to process what was taking place that night in his Skokie, Illinois home. Everything had happened so fast: The officers rapping at his front door, flashing a piece of paper in his face — saying it was a warrant — before barging in. And now the gun.

Connors served 25 months in the federal penitentiary in Oxford, Wisconsin, a medium-security prison known primarily for housing corporate crooks.

“Where are the drugs?” the officer yelled, as one or two other men began to ransack the house.

“Drugs?” Connors thought. “These guys must be kidding.” A public defender in Chicago for 30 years, Connors may have been brash and boisterous, but he was no drug dealer or user. “These guys weren’t there for drugs. They knew it, and I knew it. I didn’t have any drugs, and no one who knows me would have thought that I did.”

Then Connors noticed the other police spiriting items out his front door and into a waiting SUV — maybe the boxes of cigars he had been keeping upstairs.

It wasn’t the first time stogies had gotten him in trouble. A few months earlier, a tip from his ex-wife had inspired U.S. Customs to pull over Connors and his son, Christopher, as they entered the United States along the Ambassador Bridge into Detroit. They seized Connors’ passport, 1,150 Cuban cigars, and four bottles of Cuban rum. In his luggage, they found ticket receipts for travel on Cubana Airlines from Toronto to Havana, a Canadian customs receipt showing duty paid on 13.15kg of cigars, and a receipt from Casa Partages in Havana.

Now, lying facedown on his floor, Connors made the connection: Someone had been reading notes from his trash, discarded papers telling fictional tales of smuggled Cuban cigars and $750,000 in cash stashed in the attic — parts of a novel that hadn’t even been published yet. “Where’s the money?” the officer barked.

The Dragnet > For ten years, from 1976 to 1986, Richard “Mick” Connors established himself as a public defender in Chicago, where he grew up in an Irish neighborhood on the South Side. “My early cigar memories go back to when I was growing up in the mid-50’s,” he says. “I lived on the Irish south side of Chicago and there was a prominent cigar store in the area. I remember seeing guys smoking cigars just about everywhere.”

In between smoking cigars, his public-defender skills soon led to his being assigned to the narcotics division of Operation Greylord, a joint FBI-IRS investigation into corruption at the Cook County courthouse. The investigation eventually indicted 1 state legislator, 8 court officials, 8 policemen, 10 deputy sheriffs, 48 lawyers and 17 judges, including Judge Wayne Olson, in whose courtroom Connors had worked as a public defender for one year.

“Fixing cases in that courtroom was a daily occurrence,” Connors remembers. “I got to watch them fix hundreds of cases a month, and after a year of that it got to the point where I could spot a fixed trial just like a jeweler can spot a fake diamond.”

Back To The Home Invasion
Connors on the floor, his court-trained skill for spotting skullduggery working overtime. The men raiding his upstairs were cop types, he knew, but something was seriously wrong. “This was a cop rip-off.”

What really worried Connors, though, was that none of his assailants were wearing masks. “If they didn’t care that I saw their faces, they probably weren’t planning on leaving me in breathing condition when they left. So I thought then that I had better start thinking, real fast, of a way to escape.”

When the officer’s attention slipped, he took off running, heading for the bathroom, where he started yelling for help out the window. Startled, the intruders drove off — but not before Connors took after them in his car and got their SUV’s license number. After losing them (“They had eight cylinders, and I only had four”), he turned around and went to the police — reporting four handguns and around 74 boxes of cigars stolen — and then tracked down the owner of the car, a man identified in court documents as Tom Boratto.

According to the documents, Boratto arranged a meeting for a return of the stolen cigars and guns, during which he told Connors that the other robbers were cops. The same court documents have Boratto advising him to not pursue charges — the local police would just cover it up. But the basic fact remained: people out there thought that Connors, long known as a lifelong cigar-lover, was also a Cuban cigar-smuggler.

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The Score
The previous year, concerned that he was visiting Cuba, Connors’ ex-wife, Nicole Chakalis, contacted the local U.S. Customs office. She was eventually put in contact with agent John Sheridan, who asked Chakalis to renew her relationship with Connors in order to find more evidence.

While representatives from U.S. Customs and Border Protection, Immigration and Customs Enforcement, and the Department of Homeland Security all claim to have no record of an Agent John Sheridan, he does appear in court documents, which have him prodding Chakalis to uncover more information on her ex-husband’s activities.

On April 7, 1996, Connors had been stopped while crossing the Ambassador Bridge into Detroit, and had the Cuban cigars, bottles of Cuban rum, and passport he’d been carrying confiscated. By the time they indicted him in 2001, the government argued that one incident was merely the tip of the iceberg, with Connors allegedly making over 30 trips to Cuba over a three-year period between 1996 and 1999 — flying to Havana out of Toronto, taking the cigars back, and then storing them in nearby Windsor, Ontario.

At some point during that period, Connors also began working on a manuscript for a novel, eventually titled Cigar Runners: Sex, Cigars and Con Men in Castro’s Cuba, in which the main character says: “Getting into cigar smuggling was a fluke, it sort of just happened, and I hadn’t stayed in it for the money alone. Trafficking in contraband had brought an excitement into my life unlike anything I had ever known.”

The problem was, some people believed the adventures detailed in Connors’ discarded notes were real. The government maintained that Connors also started traveling to Cuba via Cancun; and kept his passport, which contained entry stampas from Cuba, away from Customs agents by mailing it back home or having other tourists (one Wyoming couple in particular) bring it back to the States. After a five-year investigation and a search warrant that yielded 34 boxes of cigars from Connors’ home, a federal grand jury in Chicago returned an eight-count indictment in 2001 charging him with conspiracy, smuggling goods into the United States, lying to a passport official and violating the Trading with the Enemy Act, a rarely-enforced law enacted in 1917 to regulate the transaction in foreign exchange of gold, silver, and property transfers. Today, the TWEA acts primarily as a buffer against North Korea and Cuba.

Connors fought back in court, questioning Sheridan’s investigative tactics — and arguing that the confiscated cigars, marked “Hace en Cuba,” had never been analyzed to see if they were actually Cuban. He argued that Cigar Runners, published independently in 2000 and dedicated to gonzo journalist Hunter S. Thompson, is purely a work of fiction (as was a note that misled the house-invading cops into believing he kept $750,000 cash in his home).

None of his counter-arguments stuck. After years of being sucker-punched by the combination of his ex-wife, home invaders and the U.S. government, U.S. District Judge Ronald Guzman finally delivered the twelfth-round coup de grace by handing down a 37-month sentence to federal prison and fined $60,000.

“I still think that that sentence for this kind of offense was absurd,” says Jack Cutrone, the attorney who represented Connors in his sentencing and post-trial hearings. “What the agent was instructing [Chakalis] to do in order to evade [Connors’] Fourth Amendment protections — I found that absolutely disgusting.” Connors served 25 months in the federal penitentiary in Oxford, Wisconsin, a medium-security prison known primarily for housing corporate crooks. He did some casework, and missed his daughter’s wedding — waiting all the while for release, itching to get back into court.

“He kind of felt like the government was doing a hatchet job,” says Cutrone, one of the few people willing to openly comment on the trial. “I guess it kind of depends on your view of the Cuban trade embargo. I personally think it’s ridiculous.”

In February 2007, Connors returned to Chicago and has since vigorously pursued litigation regarding his trial, even going so far as to set up a Web site,, offering $50,000 for information that could help his case. He may be tight-lipped about current dealings — “litigation is a lot like poker, and I don’t want to show my hand right now” — but he’s still more than willing to talk Cuban cigars.

“My favorite cigar of all time is the Ramon Allones Specially Selected, which is their robusto,” he says. “It’s a hard cigar to find, but it’s like anything else in life worth having: A successful hunt can lead to an extraordinary pleasure.” In the meantime, though, Connors is in pursuit of for something far more vital — to regain his name.
Amazing story!!! GREAT read Keith!

The last time there was a Tsunami at SC was many years ago when a young gentleman came in and EARNED the title of Legend Killer
- the Great Parkster

I don't even have words bro. You have absolutely blown the $hit out of me. No come back, I got nothing, speechless - The Shephard PO - RIP July 2007
A couple of interesting articles I found
WOW!  Good stuff there.
I was rivited. Thanks.
You just can't be too careful

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