Cigar Aficionado

Litigation is war and, as the chinese military strategist sun-tzu once wrote, most wars are won before they are fought. in an era where business disputes are routinely resolved by the courts, the combatants must seek every conceivable edge. * A defendant appears at his criminal trial unshaved. The attorneys argue about his appearance. An exercise in tonsorial taste? Hardly. The defendant is Vinny "The Chin" Gigante, an alleged mob boss who the prosecution claimed had attempted to avoid trial by feigning mental illness. His courtroom demeanor, down to the stubble on his face, could influence the jury's evaluation of whether he was a cunning criminal or mentally ill, and neither side would give a whisker on the point. (He was found competent-and guilty.)

If a sixteenth of an inch of facial hair can influence a trial, is it unreasonable that a cigar can turn the tide in a multimillion dollar business dispute?

Cigars and lawyers have a long and close history. During an opponent's closing argument, Clarence Darrow would run a paper clip through his cigar, letting an enormous ash build, mesmerizing the jurors and, of course, diverting their attention.

As a young attorney, I interviewed Louis Susman, attorney and adviser to the Busch brewing family, through a haze of smoke. I took the deposition of Asher Edelman, once-corporate raider and now art collector, while he savored a Montecristo. Those days are gone, though, and they aren't coming back.

Or are they?

I was representing the plaintiffs in a business dispute involving a failed public stock offering. One of the defendants was a professional leveraged-buyout investor. He possessed uncanny business timing, $500 million and the ability to make himself invisible.

While preparing to take his deposition, I naturally planned to bring to bear every bit of knowledge I possessed about the case. I also searched the public record for any additional information I could find about his other business dealings and personal characteristics.

I could learn virtually nothing from the few details reported about this Spectre. There was, however, one picture of my opponent in the public domain, and from that picture, I hatched my plan.

He was smoking a cigar.

I resolved to coax this man into smoking a cigar with me during his deposition. He would, of course, be far too cagey to lower his guard merely because I offered him a fine cigar and a moment of relaxation.

I set my sights on his lawyer. His lawyer in this case was a partner in a large New York law firm, unreadable, unflappable. The Sphinx, I called him. Although the deponent's connection with this business dispute was secondary, he and his lawyer were key players in any resolution. They were, until this time, unreachable.

The Spectre was the last of the Sphinx's four clients to be deposed. Over a period of two weeks, in the Sphinx's stuffy white-shoe law office, I conducted the depositions. There were a few revelations, but only a few, and the Sphinx could not have been displeased with the testimony.

On the last day, at moments before 10 o'clock, The Spectre entered the conference room with The Sphinx and I introduced myself. Just as we were about to begin, I said, "Excuse me for asking, but I heard a rumor that you are a cigar smoker."

"That's right," said The Spectre, perhaps a bit surprised both that I knew this and that we were talking about it as the court reporter prepared to take down our words.

"If I could produce some really exceptional cigars, do you think it would be possible for us to smoke them here?"

There were really two answers to such a question. The building and the law firm were plastered with No Smoking signs. On the other hand, this man was one of this huge firm's biggest clients, big enough that he and the firm's managing partner prepared for the deposition over a weekend of golf in Bermuda. (You can learn a lot by listening to small talk prior to a deposition's opening moments.)

Not giving him a chance to respond, I pulled out two Hoyo de Monterrey Double Coronas. Even men with a half billion dollars don't have as many Hoyos as they want.

His eyebrows danced. He asked his attorney, though the answer he sought was already clear. "That's not a problem, is it? If we smoke these in here?"

It was a LARGE problem. Anti-smokers, used to smoke-free offices, do not relinquish their ground easily. Someone would have to be employed outside the door, just to keep angry office staffers from barging in and disrupting the deposition, or worse, riling the firm's biggest client. It also meant The Sphinx was losing control over the environment, in his own office.

"That's fine," The Sphinx said, grasping for straws, "but I'm not sure if it's fair to subject the court reporter..." His voice trailed off.

Checkmate, Sphinx.

During the previous two weeks, I had seen the reporter make numerous trips down 50 floors in the elevator to take cigarette breaks. The court reporter was thrilled to have cigars smoked during the deposition, and she told The Sphinx so.

Where they found the crystal ashtray, I do not know, but we spent the next two hours in mental combat, blowing huge clouds of Hoyo de Monterrey smoke across the table.

I couldn't say at the time that the victory was any more than moral. The Spectre had not become one of the most savvy businessmen in the world for no reason and, cigars or not, he simply would not testify to anything damaging his side's interest.

As the case neared trial, however, I locked horns with The Sphinx over a potential settlement of the case. With the large amounts at stake in such disputes, a settlement would not be an unexpected conclusion. Settlements, however, require compromises, and warriors are loathe to compromise.

Informal discussions proved unproductive. The judge encouraged the hiring of a mediator, a former judge, to help bring the parties together. I thought the most likely outcome would be a settlement of about $1.75 million, so my co-counsel and I were evaluating whether to recommend acceptance of such a settlement.

After a long day of negotiations and several more days of telephone calls with each other and the mediator, the case settled for $4.25 million.

I would never claim that two cigars had any impact on the difference between the $1.75 million we expected and the $4.25 million we accepted. Even if my gamesmanship influenced the outcome, it is best to heed Sun-tzu and give the adversary a route to escape with honor.

At least I thought I was allowing him the escape route. The day after the settlement became final, The Sphinx sent me a box of Hoyos. Sometimes, I think it was a sign that we left some money on the table. On the other hand, you can never have too many Hoyos, so I have enjoyed every one. *

Michael Craig practices law in Chicago and writes about cigars and popular culture.