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Philip H. Corboy, Sr. Named One of Chicago's 30 Toughest Lawyers

James Ylisela
30 Tough Lawyers, Chicago Magazine

They are gladiators of the courtroom, blue-suited warriors whose weapons are their legal acumen, their verbal derring-do, and their bulldog tenacity. Meet 30 men and women you don't want to see in court - unless they're on your side.

One targeted a man running for governor. Another used images of Smurfs to humiliate his client's accusers. Still another dismantled experts testifying for Vice-President Gore with the Presidency on the line. These three are among the toughest lawyers in Chicago - a select collection of legal talent who have won hundreds of millions of dollars in judgements, sprung countless people accused of crimes, put away crooks and murderers, and litigated some of the most pressing issues of the day.

When we set out to find the toughest lawyers in town, we were looking for men and woman who were smart, innovative, skilled, and relentless advocates for their clients. After talking to scores of lawyers, we came away with a few other ideas about what it means to be tough. One element is preparation. Many of our sources told us that what often passes for toughness is an almost obsessive knowledge of the facts and arguments - a level of command that could overwhelm an opponent. Another element was focus - the ability to zero in on the key issues and not be diverted, in court or in negotiations.

One thing that doesn't make a tough lawyer, our sources said, is a mean streak. Being harsh and cold is almost always counterproductive. "You won't get anywhere if you're a bully or a jerk," says Jerold Solovy, the litigation veteran from Jenner & Block.

We came away with a few other observations about toughness. Most of the men and woman on our list make a good buck, though a few of them get by in cramped offices, their desks and floors piled high with legal files and transcripts. For these lawyers, the toughness often comes from fighting for the same principles for decades.

Some of the lawyers on our list hardly know what it means to lose. Others fail more often than they succeed, taking on cases that are difficult, if not impossible, to win. For example, three of our lawyers - Ed Genson, Terry Gillespie, and Bill Hooks - defended former U.S. representative Mel Reynolds in his various criminal trials. All three lost. And then there's Dan Webb, arguably one of the top trial lawyers in the country, who also holds the distinction of having lost the largest punitive damage verdict in U.S. history, the $145-billion judgement against Philip Morris. All four men say they'd do it again.

In compiling our list, we talked to lawyers and judges, as well as journalists, professors, and other observers of Chicago's legal scene. We tilted toward litigators and people who end up in court, because that's where toughness usually is most readily apparent.

Any collection of this sort is bound to be somewhat arbitrary, and in Chicago any list of 30 names could be supplanted by another. An alternative list might include such people such as Fred H. Bartlit, a legendary litigator who has mentored some of the best lawyers in town, including two profiled here: Emily Nicklin and Philip Beck. New U.S. attorney Patrick Fitzgerald comes to town with a reputation as a topflight prosecutor. Another tough lawyer, Susan Getzendanner, has been doing and saying pretty much what she pleases since her days on the federal bench. "I try to dominate the courtroom, and some people don't like that," she says. And few lawyers have been tougher than former Illinois Appellate Court justice R. Eugene Pincham.

But we think the men and women listed below (in no particular order) make up an all-star team of the fiercest legal talent in town. And if you don't believe us, just try crossing one of them in court.

Corboy & Demetrio, Personal Injury

In a career that has spanned more than 50 years, Phil Corboy has become the dean of Chicago's personal injury lawyers, handling countless high-profile cases and launching several top lawyers into the field. Still, he insists, the secret to his success is simple: preparation. "Once you start making asssumptions that you can do something by the seat of your pants, you're in trouble," Corboy says.

Robert Clifford, who learned from Corboy, saw the technique firsthand." Corboy knows his case and knows what is in the depositions better than anyone,"Clifford says.

Corboy prepares for battle with brainstorming sessions, focus groups, and, when the case demands it, full-fledged mock trials, complete with cross-examination and two different sets of juries to test different strategies. "I know I'm not the smartest lawyer in the world, but for [any given] lawsuit, I'm the [best] lawyer to try that case," he says.

His portfolio of large cash settlements is thick. To mention just a few: In 1982, he represented the families of those who had died after taking Tylenol laced with cyanide. He has been lead counsel in numerous successful lawsuits on behalf of the victims of airline crashes, including the 1989 United Airlines DC-10 crash in Sioux City, Iowa, and the 1994 crash of a US Airways jet near Pittsburgh.

Would Corboy consider working for the defendant in a big personal injury case? "That's representing organized money," he sniffs. "I can't see any fun in that." 

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Corboy & Demetrio
33 N. Dearborn Street
21st Floor
Chicago, IL 60602