Dan Webb of Winston & Strawn Courtesy photo

As the U.S. attorney for Chicago in June 1984, Dan Webb made legal history when a federal jury returned a guilty verdict in a bribery case against a Cook County judge. He also breathed a sigh of relief, as the conviction meant calls that he be disbarred would go unheeded.

The conviction was part of what would come to be known as Operation Greylord, a controversial investigation into corruption in the Chicago judicial system that led to nearly 100 indictments and the convictions of 15 judges and 50 lawyers.

Webb and others employed innovative tactics to root out the corruption, including bugging a judge’s chambers; recording lawyers’ and judges’ phone conversations; and sending undercover agents to pose as corrupt prosecutors and lawyers.

“There’s nothing wrong with victory,” Webb says. “Once we won these cases, nobody decided to discipline us, and it went away.”

Ever since, Webb has forged a distinguished careers as a trial lawyer at Winston & Strawn, where the 71-year-old is co-executive chairman. He has also put his investigative skills back to work as a special prosecutor, including an assignment in the wake of the Iran-Contra affair, when he was appointed to prosecute the former National Security Advisor John Poindexter.

While he has earned hard-fought courtroom victories on behalf of some of the largest American companies, including General Electric Co. and Philip Morris International Inc., Webb says his finest argument may have come before he was even admitted to the bar: his personal appeal to the dean of Loyola University Chicago School of Law.

A self-described farm boy from downstate Illinois, Webb traveled to Chicago for the first time after his junior year at Western Illinois University asking to be accepted to law school before finishing his undergraduate degree. Webb won over a reluctant dean.

He has spent a career swaying juries with a straightforward courtroom style that often attempts to boil down complex cases to one singular question. While he uses no notes in his openings or closings, he says he spends weeks editing scripts that he commits only partly to memory. He doesn’t want the jury thinking they’re listening to a script.

Webb remains busy, trying four cases in about the last year. Webb played a somewhat unfamiliar role in the latest trial: representing the plaintiff. His client was a meat processing company that sued ABC News for defamation related to reports calling the company’s product “pink slime.” The case settled shortly before Webb finished his arguments in a South Dakota courtroom.

For Webb, it is the latest journey in a career that was encouraged by a high school guidance counselor who saw him excel in a debate program and handed him books on trial lawyers, including one of his favorites, Clarence Darrow.

“I read that stuff and I decided I don’t care what happens,” Webb says. “I’m going to become a trial lawyer.”

Advice to 
Young Lawyers:
 “It doesn’t matter how smart you are. It doesn’t matter how quick you think you are on your feet. You have to work harder than your opponent.”