At first blush, this seems harsh. Yes, Cuban cigars are contraband under the "Trading with the Enemy Act" (co-sponsored by Rep. Julia Roberts, D-Hollywood). So the attorney certainly committed a crime. But jaywalking is a crime too. Moreover, this is a curious law that in modern times could be renamed "We Need Florida's Electoral Votes, And There Are Lots of Cuban-Americans There Act." As of 2008—when North Korea lost its "enemy" status—Cuba is the only country that comes under the law. So, in another sense, "Trading with The Enemy Act" is the perfect title for the law, because we have only one enemy now, and it is Cuba. Finally, it has always seemed odd to me that the U.S., capitalist dynamo that it is, has chosen to respond to the threat of Communism on that tiny Caribbean island by refusing to trade with it. Isn't it the capitalists who think trade is good and civilizing?
Anyhow. Upon investigation, the story here is a little more complicated. First, even before the Cuban cigar affair, this particular attorney had been suspended for converting (that is, stealing) about $8,500 from settlement funds in a personal injury case. The suspension, which stems from conduct in 1999, still stands because he hasn't yet made restitution. Second, this guy isn't some fat-cat at risk of losing his law license for ordering his Cuban cigars over the internet. No, his activities were quite a bit more ... involved: he made dozens of trips to Cuba (supposedly to visit a girlfriend he was trying to, well, import) and was eventually stopped at the Canadian border with 46 boxes of Cuban cigars in his trunk. As a result, he was indicted by federal prosecutors, tried by a jury, convicted, and sentenced to 37 months in federal prison.
But let's back up to the girlfriend in Cuba for a moment, because we haven't gotten to the juicy stuff yet. My guess is that if his activities had been limited to mere smuggling, he would never have been caught or disciplined. What did him in was the canoodling. Because the source of his undoing was not crack investigative work by customs officials. No, what did him in was his ex-wife, who ratted him out to the feds and guided their every move along the way—she even went so far as to rekindle the relationship for the sole purpose of gaining intelligence for the sting. Cold-hearted!
In the 7th Circuit opinion affirming the conviction, Judge Evans points out the real cautionary tale here:
Divorce rates are disturbingly high. Sometimes, marital splits get nasty when an ex-spouse decides to dish out a little dose of discomfort to his or her former partner. And as far as dishing out discomfort is concerned, the havoc visited on Chicago lawyer Richard Connors by his ex-wife would win a gold medal for creativity. With substantial assistance from his ex, Connors stands convicted in federal court of (among other things) violating a law we seldom encounter, the Trading with the Enemy Act (TWEA), 50 U.S.C.App. §§ 5(b)(1) and 16.Here's my (non-legal!) advice for lawyers looking to maintain their license. If you must, go ahead and discretely trade with the enemy (i.e., Cuba). It's no big whoop. And, should the mood strike you, go ahead and sleep with the enemy. We're all adults here. But don't trade with the enemy and sleep with the enemy. That is just too much.