Chicago Lawyer’s 2008 Person of the Year: Dan Webb

By Maria Kantzavelos

In his corner office on the 46th floor of the downtown skyscraper that houses Winston & Strawn, Dan K. Webb, who usually arrives for work by 7 a.m., emerges from a desk covered with the case files of multiple clients, files stacked in growing piles.

Speaking in a slightly folksy fashion and a voice that offers a hint of his rural, west-central Illinois roots, the big-firm chairman is known as one of the most sought-after lawyers in the country. On a Monday evening in late October, his hand is smudged with ink as he leafs through the pages of his date book.

Days before one of his clients, longtime Republican power broker William Cellini, was indicted in the Operation Board Games probe of corruption in state government, the famed litigator’s workweek was to play out something like this:

A day in Chicago to prep a witness for an upcoming trial in California, sandwiched between two days in New York to meet with a client and attend a bar association event. Then more meetings back in Chicago on Friday.

”That’s my life this week,” Webb said, matter-of-factly.

It’s no wonder Webb says he doesn’t keep count of his cases.

”At any given time I may have … 20 to 30 client matters going on at the same time. They’re not all popping at the same time every day, but I have a fairly heavy caseload,” he said.

But it is when Webb is on the brink of trial or in the midst of the courtroom contest — putting in 15- to 18-hour work days with his mind focused intensely on the ins and outs of that one case — that he steps into a world he relishes most.

”I love trying cases. It’s what drives me. It gets my cork a bobbin’ and I love it,” Webb said. ”I like pressure. I like stress. And, I like moving. I thrive in that world.”

Now 63, Webb rose to prominence in Chicago in the early 1980s as the U.S. attorney who oversaw the landmark Operation Greylord probe of judicial corruption. He went on to successfully prosecute Iran-Contra operator John Poindexter, and has spent the last two decades in private practice defending corporations like Philip Morris, Microsoft, and General Electric, and a host of politicians, including former U.S. Rep. Dan Rostenkowski and former Illinois Gov. George H. Ryan.

It is Webb’s enormous preparation, his willingness to take tough cases and his down-home, ”winning way” with juries and judges that sets him apart from other excellent trial lawyers, said former Illinois Gov. James R. Thompson, who stepped down from Winston’s top leadership post in 2006, when Webb became its chairman.

”He’s No. 1,” proclaimed Thompson, a close friend and mentor of Webb’s since the early 1970s, when Webb was cutting his teeth as an assistant U.S. attorney in the Northern District of Illinois, where Thompson held the top spot as U.S. attorney. ”He just exudes sincerity. No court or juror would ever think that Dan was telling them something that wasn’t so.”

Described as a true ”generalist trial lawyer” who eagerly takes on caseloads that are impressive because of their volume, variety, and complexity, Webb is ”one of the more formidable courtroom lawyers in America today,” said prominent Washington, D.C., attorney Brendan Sullivan of Williams & Connolly, who has opposed Webb in several high-profile cases.

”He doesn’t pick the cases he can win and just try those. He steps into the arena and fights the good fight for his client, whether he’s the underdog or the favored,” Sullivan said. ”In this day and age, where you have so many so-called trial lawyers who don’t ever get to court, or if they do it’s once every 10 years — they’re the great pretenders. But Dan is the real thing.”

In recognition of an illustrious career that is rooted in Chicago, his resilience and doggedness as a trial lawyer who has long maintained his standing at the top echelon of his profession, with a reputation that extends beyond the United States, Webb has been selected Chicago Lawyer’s 2008 Person of the Year.

A passion for action

If the rule of thumb in real estate is location, location, location, Webb has one that sums up his passion for trial work.

”Action, action, action. I like the action,” he said, with a wide-eyed, kid-in-a-candy-store enthusiasm. ”I like the pure excitement of constantly being on stage, on trial, where you’ve got to get up and cross-examine a witness, you’ve got to give a closing argument, you’ve got to live by your wits.”

Webb’s genuine love of trying cases comes across clearly to his friends and colleagues.

”He is driven to be an extraordinary trial lawyer,” said 7th U.S. Circuit Court of Appeals Judge Joel M. Flaum, who has known Webb since the early 1970s, when Flaum served as a top assistant in the U.S. attorney’s office. ”He’s not a very materialistic guy. He’s not a guy that needs to have the most expensive watch, or car, or clothes. It’s just the love of trying cases.”

Beyond his skills as a ‘’stunningly good trial lawyer,” Webb embodies the traditional values of the profession, said Jenner & Block chairman Anton R. Valukas, a former U.S. attorney.

”He represents part of the old school — lawyers who can brilliantly try a case and then go out afterwards and share a glass with their opponent, knowing that both of them tried to their best,” Valukas said. ”It’s not about the money, it’s about the challenge.”

For Webb — who is said to consistently work more than 3,000 hours per year in a practice that mixes complex commercial litigation and white-collar criminal defense — 2008 has been especially busy.

This year he faced the likelihood of at least six trials, including the widely publicized defense of Detroit Mayor Kwame Kilpatrick, who recently entered a plea bargain agreement and was sentenced to four months in prison.

In a victory last year, Webb led a Winston trial team to a $58 million jury verdict for his client, Verizon Communications, in a patent infringement case in an Alexandria, Va., federal court against Internet phone company Vonage.

This year, while facing the prospect of about a half-dozen trials, Webb also served as chair of the Chicago Bar Foundation’s 2008 Campaign for Justice, which raised more than $1 million, a record-breaking amount for a citywide effort aimed at increasing the compensation of Chicago’s legal aid attorneys.

On a Webb trial team

At Winston & Strawn, the most sought-after assignments are to work with Webb, said managing partner Thomas P. Fitzgerald.

Being on a trial team with one of the best known trial lawyers in the country is never a ”’Mr. Webb’ thing — it’s ‘Dan,”’ said Thomas J. Frederick, a Winston partner who chairs the firm’s litigation department.

”Dan is a very even-keeled guy; very easy to work with. But he’s never happier than being on trial,” said Frederick, who has worked with Webb since 1989. ”There’s a real esprit de corps that breeds around a Webb trial team.”

In his dealings with people, from support staff to associates, partners and clients, ”there is no aspect of the prima donna to Dan — none,” said Bradley E. Lerman, a Winston litigation partner who works with Webb on major matters. ”He demands a high level of performance from everybody, but he’s as approachable and as ordinary as anybody, in terms of just a genuine, good person, dealing with people.”

Being on a Webb trial team also means its leader is the hardest worker of them all.

”People who think that the skill and the excellence they see in the courtroom is, somehow, the work of inspiration and not perspiration are missing the essential feature of Webb, which is, he simply outworks everybody,” Lerman said.

During his occasional downtime, Webb might catch a Cubs game at Wrigley Field, square off in a tennis match, or take a chance on some horseracing at the track or at a few rounds of poker or blackjack (”I was just in Las Vegas trying a case in Reno, and I taught everyone on my team how to play blackjack,” he said).

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