Cigar-bage

Imagine playwright William Congreve (“Heaven has no rage like love to hatred turned, Nor hell a fury like a woman scorned.”) teaming up with author and poet Rudyard Kipling (“A woman is only a woman, but a good cigar is a Smoke.”) to weave the tale of a federal prosecution.

In the case of Chicago lawyer Richard Connors, it's as if that happened. His saga is rife with juicy plot twists.

At the center of the story is Connors' ex-wife, who dishes out a dose of discomfort to her former mate worthy of a “gold medal for creativity,” according to a federal appeals court opinion, by allegedly placing incriminating documents in the trash for government agents to retrieve.

In 1996, thanks to a tip from his ex-wife, Nicole Chakalis, authorities stopped Connors at the Canadian border on his way back to the United States and seized a trunkload of Cuban cigars.

Over the next three years, Special Agent John Sheridan of the U.S. Customs Service, aided by information from Chakalis, continued to investigate Connors' cigar smuggling operation.

The government eventually brought charges against Connors. Following an 11-day trial, a federal district court jury found Connors guilty of smuggling Cuban cigars into the United States and, incidentally, violating the Trading with the Enemy Act. Since shortly after Fidel Castro assumed power in 1959, Cuba has been a major target of the Act, which imposes an embargo on Cuban products. Connors was sentenced to three years in prison and fined $60,000.

Connors was unaware of his ex-wife's cooperation with the investigation until after the trial, when “apparently remorseful, she told him what she had done,” according to court documents. At a post-trial hearing, she testified that Sheridan asked her to renew her relationship with Connors, spend time at his house, remove telltale documents and throw them into the trash where Sheridan could retrieve them without a search warrant. For his part, Sheridan admitted taking items from Connors' garbage, but denied urging Chakalis to put anything there for him to find.

The district court found no violation of the Fourth Amendment. For one thing, the court did not believe that the activities Chakalis described amounted to an illegal search because Connors himself allowed her into his home. For another, the court did not find Chakalis' testimony regarding her dealings with Sheridan to be reliable or credible, and instead believed Sheridan's testimony that he neither encouraged nor knew about Chakalis putting documents into the trash.

On appeal, Connors was again unsuccessful in his Fourth Amendment argument and his conviction was upheld.

“The fact that Chakalis was spying on Connors and exploiting his misplaced trust in her does not by itself amount to a constitutional violation, even if it was at the behest of the government,” the opinion stated.

“Rummaging through Connors' private files for incriminating documents, however, may be another matter … but only if Sheridan directed or acquiesced in it,” the court added.

The appellate panel declined to second guess the district court's conclusion that Sheridan did not know about any illegal prying.

[U.S. v. Connors, 441 F.3d 527 (7th Cir. 2006)]

The legal editor welcomes comments from readers. Contact Barry Shanoff via e-mail: [email protected].

The columnist is a Rockville, Md., attorney and serves as general counsel of the Solid Waste Association of North America.