You want to be Dan Webb. You want Jack Welch calling you when his divorce gets ugly. You want John Reed, a man you’ve never met before, asking you to get to the bottom of how Richard Grasso ended up with nearly $200 million from the New York Stock Exchange. You want former Illinois governor George Ryan reaching out to you when federal prosecutors indict him for fraud and racketeering. You want The New York Times anointing you a “superlawyer”; clients falling over themselves to pay your $700-an-hour fee. It must be great to be Dan Webb.

You want to be Dan Webb? This is how you would have spent most of May. Holed up in Gilmer, Texas, a fleck of a town in East Texas whose claim to fame is its annual Yamboree yam festival. Stepping over two months’ worth of cigarette butts, in blast-furnace heat, on your way to a courtroom squeezed into the building housing the county jail. Dodging rabid pickup trucks as you walk the cracked asphalt to a rented office next to the Tater-Town Barbershop, where you’ll gulp down a lunch of chicken strips. Leaving court at the end of the day and driving 25 miles to the nearest decent motel, across from the Waffle House, to start preparing for tomorrow.

You’re spending three weeks in Gilmer because your big drug company client, Wyeth, is accused of heartlessly toying with the health of a sweet mother of two who took the diet-drug combination called fen-phen. Two weeks earlier, in another fen-phen case, a jury in Beaumont, Texas, clobbered Wyeth with a $1 billion verdict. Desperate to stanch the courtroom bleeding, Wyeth asked you to drop everything and hightail it to Texas.

You’re working night and day to contain the damage. Then, near the end of trial, a bolt of bad luck. The U.S. Court of Appeals for the Third Circuit overturns a lower court and allows a pile of damaging evidence to be admitted in fen-phen cases around the country. Wyeth settles. You leave town without a verdict.

Webb is used to anticlimactic endings. Eight times in the last two years, the marquee partner at Chicago’s Winston & Strawn has plunged into a case, often right before the scheduled trial date, furiously geared up, only to be forced to walk away without finishing the fight. Earlier this year another fen-phen case in Madison County, Illinois, was postponed on the day of jury selection. A trademark case for Microsoft Corporation against Lindows, Inc., set for trial in March, was delayed shortly before its starting date. A showdown over Grasso’s pay, to be played out in a suit filed by New York State attorney general Eliot Spitzer, was derailed when Grasso’s lawyer, Brendan Sullivan, Jr., of Williams & Connolly, filed a surprise request for a transfer from state to federal court.

Starting this month, Webb, 58, may get to go the distance. The “mother of all trials,” as Webb likes to put it, it is set to begin-the U.S. Department of Justice’s $280 billion racketeering suit against the tobacco industry. Webb will be lead trial lawyer for Philip Morris USA Inc., the nation’s biggest cigarette maker.

The tobacco giant’s trial team also includes an arsenal of major firms: Arnold & Porter; Hunton & Williams; and Paul, Weiss, Rifkind, Wharton & Garrison. William Ohlemeyer, vice president and associate general counsel of Altria Group, Inc., the parent company of Philip Morris, says Webb is the “best fit” to lead this army. For one thing, he has represented the company in similar cases, such as the attorney general suits brought by Texas and Washington State. (The Texas case settled on the eve of trial, and Washington settled ten weeks into trial.) Ohlemeyer also praises the “great team” from Winston & Strawn behind Webb, including partners Thomas Frederick and Kevin Narko.

But, perhaps most important, is Webb’s personality: He’s a famous trial lawyer who is able to keep his ego in check. Lawyers from other firms like him and work well with him. Along with Philip Morris’s band of law firms, Webb is coordinating efforts with counsel for the other defendants, including: Jones Day, representing R.J. Reynolds Tobacco Company; Kirkland & Ellis, for Brown & Williamson Tobacco Corporation; St. Louis’s Thompson Coburn, representing Lorillard Tobacco Company; and New York’s Kasowitz, Benson, Torres & Friedman, for Liggett Group, Inc. “It’s a big challenge to get all the lawyers coordinated to the point where they can put on an efficient, effective defense,” says Ohlemeyer. “There’s a handful of lawyers who could have done that.”

Kirkland partner David Bernick, who will be Brown & Williamson’s lead trial counsel, describes Webb as “very down-to-earth and easy to get along with.” Bernick continues, “I’ve never seen him lose his temper or talk down to somebody. . . . Dan is a guy I genuinely look forward to trying a case with.” The Kirkland partner adds, “I’m not a wallflower. I’m not always easy to get along with. That says a lot about Dan.”

The Clinton Justice Department filed this suit in 1999, seeking reimbursement of health care expenses under two relatively obscure statutes, the Federal Medical Care Recovery Act (MCRA) and the Secondary Payer Act. It also lobbed in civil claims under the Racketeer Influenced and Corrupt Organizations (RICO) act, charging the industry with conspiring to conceal the dangers of smoking and its marketing plans for children. It sought disgorgement of the defendants’ “ill-gotten gains” from 1954 until 2050 and a host of monitoring measures.

When President George Bush took office at the start of 2001, skeptics predicted the Republican administration would drop this suit. It didn’t. Each side has scored some pretrial victories. In 2000 Washington, D.C., federal district judge Gladys Kessler, who will preside over the trial, granted the industry’s motion to toss out the MCRA and Secondary Payer Act claims, holding that Congress did not intend these laws to be used to recover costs like these. But the Clinton appointee refused to dismiss the RICO elements. The industry has filed an interlocutory appeal of Judge Kessler’s decision to allow the government to seek disgorgement of profits under RICO. Judge Kessler has indicated she will start the trial before the U.S. Court of Appeals for the D.C. Circuit rules.

If, as expected, the case goes to trial on September 13, Webb will face a team of Justice Department career attorneys, led by deputy attorney general Sharon Eubanks [see " 'Tenacious Litigator' Leads the Way for Justice, page 122]. The government’s team, which includes roughly 25 lawyers, is vastly outnumbered by the industry’s army.

If you were Dan Webb, you’d have to sit in a courtroom facing a small-town jury and listen to the opposing counsel paint you as a slick city lawyer who is in bed with Big Tobacco. During jury selection in the Gilmer fen-phen trial, plaintiffs lawyer Douglas Monsour pointed out Wyeth’s army of lawyers, then confided to the local residents: “The primary reason that I’m concerned, it’s not all the lawyers that I’m really worried about, it’s Mr. Webb here. He is from Chicago. He’s very, very good. He’s a much better lawyer than I could ever dream of. We all aspire to be Mr. Webb as a lawyer, but only a few people get there.” Monsour then told the potential jurors that Webb had defended Philip Morris in a suit brought by their very own state of Texas. “They wrote an article about it in Business Week. . . . It’s called ‘Can Dan Webb Pull Big Tobacco Out of the Fire?’ . . . Okay. Here’s what I’m worried about. . . . I’m worried that Mr. Webb is going to pull Wyeth out of the fire on this one.”

Monsour, a partner in the four-lawyer Sloan Monsour firm in Longview, Texas, admits he had never heard of Dan Webb before the Chicago lawyer popped up in this case a month before trial. So the 35-year-old lawyer called up some friends in the plaintiffs bar and got the bad news. “I said, ‘Oh, shit. He’s the real deal. When Jack Welch or Bill Gates are in trouble, they call him.’ “

During the trial Monsour acted like the one who owned the courtroom, tipping back in his chair and playfully twirling a binder clip on his pinkie finger. Webb hunched over counsel’s table, furiously writing on a pad of paper with all the diligence of a fourth-year associate whose career depended on catching every word. Occasionally Webb would lean back and assume his stock position: one hand crammed under the waistband of his pants and the other holding a pen that he gnawed with his back teeth.

Webb’s cocounsel, Don Griffin, Jr., from Vinson & Elkins’s Houston office, possessed the down-home Texas accent and patter. But Griffin couldn’t hide the sheen and polish that screamed “big-firm lawyer.” Webb, who grew up in a small Illinois town not unlike Gilmer, could pass as a local insurance agent, with his slightly stooped shoulders, loose-fitting gray suit, scuffed loafers, and lank brown hair slipping onto his pale forehead.

When Webb stood to examine a witness, he placed a ring binder on a plastic garbage barrel that served as a podium. Last year Webb’s peers voted him the nation’s top white-collar lawyer in a survey by the newsletter Corporate Crime Reporter. Given his reputation, you expect him to burst with charisma and dazzle. You eagerly await the sizzle. But nothing exciting happens. Webb is simply up there doing his job. Diligently. Thoroughly. Without fanfare. No great orator, he speaks in a voice that’s slightly high-pitched and staccato. He wraps his arms around his body and rarely gestures. He’s working, not putting on a show.

Shortly before a break, Webb spots an oversize cockroach touring the courtroom. When the judge adjourns, Webb chases down the critter, lifts his foot, takes aim, and smashes the bug on the carpet. He looks pleased.

“He’s not what I expected at all,” says Monsour. “I expected a hard-ass, and he’s not. . . . He’s a real good guy. . . . I’d call him up at 11 at night and say, ‘What are you doing?’ He’d say, ‘What do you think I’m doing?’ I said, ‘Get down here!’ I’d pour some Scotch and we’d shoot the breeze.” The Texas lawyer offers a professional assessment: “A lot of defense lawyers out there I think are awful and don’t have good judgment. He’s got good judgment.”

In an interview after the case settled, one juror says that given all the buildup that Monsour gave Webb, he was disappointed. “I expected to see some fantastic lawyer at work. It never came about to fruition,” says Huey Mitchell, a retired telecommunications manager for IBM Corporation. Still, says Mitchell, he was leaning toward voting for Wyeth, because he thought the plaintiffs’ evidence wasn’t convincing. Another juror, David Holloway, had a hard time remembering which of the many lawyers was Webb. “Is he the one who looks like that actor, the one who was in that movie with Nicolas Cage, Con Air?” asked the 26-year-old grocery store clerk.

Even if Webb didn’t wow these two jurors, others appreciate his style. “I think Dan is a very easy guy to underestimate,” says former Sullivan & Cromwell partner Michael Lacovara, who worked with Webb on the remedies phase of the Department of Justice’s antitrust case against Microsoft. “He’s not a snappy dresser. He’s not a polished guy,” says Lacovara, who left the Wall Street firm last year to join investment bank Sandler O’Neill & Partners, L.P., as a principal and general counsel. “But what he is is sharp. . . . There are not many rooms where Dan is not the smartest person there.”

“Dan is not the silver-tongued orator,” says Microsoft vice president and deputy general counsel Thomas Burt. “I think he comes across to jurors as a highly credible advocate, an everyman sort of person.” Burt says that when he hired Webb to join Sullivan & Cromwell on the antitrust team, he “wanted someone who could play well with others.” He adds, “He’s not the kind of guy who comes to a meeting or the courtroom with a great deal of ego on his sleeve.”

“Dan is a real straight-up guy,” says Altria’s Ohlemeyer. “That’s the reason his name is attached to so many things. . . . The businesspeople really like him and really respect him. He speaks candidly and directly to them. A lot of lawyers don’t have the confidence to do that.”

Webb’s confidence comes from the experience of trying more than 100 jury cases, and an estimable record of success. Other lawyers can match his list of victories, but there’s something about Webb’s genuineness that inspires exceptional trust and loyalty. “I know a lot of lawyers who come from similar backgrounds [as Webb], but you would think they’re one generation removed from English royalty,” says Lacovara. “Dan has not reinvented his exterior.” Says Webb’s partner, Bruce Braun: “Despite all the trappings of excellence, prestige, and wealth, he’s just a normal, really nice guy.”

If you were Dan Webb, you would have had to stand in a Miami courtroom on a hot July day in 2000, and listen as your client, Philip Morris, and its competitors were smacked with the largest verdict in U.S. history in Engle v. Liggett Group Inc.-$145 billion in punitive damages. Your reaction would have been broadcast around the country by television cameras. Live.

Webb had stepped into Engle after the defendants were already in bad shape. Before Webb was involved, in the first phase of this class action, the jury found that smoking caused many of the class’s injuries and that the tobacco companies’ conduct warranted punitive damages. (The class includes all Florida residents who suffer from diseases caused by an addiction to nicotine, and survivors of those who have died.) Philip Morris asked Webb to jump into the case to try to limit the punitives. He figured he’d be there for a couple months. It turned out to be more than a year.

“We knew going in we were in deep trouble,” says Webb’s partner Bradley Lerman, who tried the case with him. Lerman recalls the sinking feeling that he and Webb got the first time they watched the Engle jury enter the courtroom: “It was as bad a feeling from a jury as I’ve ever had. . . . You could just see the looks on their faces-it was not warm.” Still, Lerman says, Webb thought he could turn things around. “[Webb] felt he could go down there and pull something out of his hat that would save a grim situation.” Lerman says Webb’s strategy for this case and others is simple: “He rolls up his sleeves and works through the facts with each witness. . . . Dan doesn’t get mad, he operates in the courtroom like a doctor in an operating room.”

Like everyone else interviewed for this article, Lerman stressed Webb’s exhaustive preparation. His team of lieutenants work up materials for him, but he doesn’t just lean on their work. “He doesn’t take outlines from an associate or junior partner and walk into court with it,” says Lerman. When preparing to examine a witness, Webb leaves nothing to chance. He writes out the exact wording of each question. Lerman recalls the effort Webb put in before cross-examining a major plaintiffs witness in Engle: “He reworked that outline 12 to 15 times. . . . It is worked and reworked and reworked till he has it perfect.”

During the excruciatingly lengthy Engle trial, Webb refused to let the team dwell on their predicament. “He didn’t want to hear about complaining,” says Stephen Zack of the Miami office of Boies, Schiller & Flexner, who was Philip Morris’s local counsel. “That’s yesterday’s news. Let’s look forward.” To release frustration, Webb would lace up his running shoes and take off down the road. Says Zack: “I think the running kept him sane.”

When the jury announced its stunning verdict, Webb predicted it wouldn’t stand. Last year a Florida appellate court nullified the Engle verdict and decertified the class, finding that the plaintiffs’ claims varied so much that they should not be tried as a class. (Webb’s partner Stuart Altschuler led Winston & Strawn’s efforts on the appeal; Elliot Scherker of Greenberg Traurig and Alvin Davis of Steel Hector & Davis argued the case in the appellate court.) This victory for the tobacco companies was thrown into doubt in May, when the state supreme court decided to hear the plaintiffs’ appeal of the reversal. A hearing is set for November.

Webb has tried one other tobacco case for Philip Morris: a suit filed by the state of Washington that went to trial in 1998. It settled for $4.5 billion ten weeks into trial, when the Master Settlement Agreement between the industry and 46 states was struck. Jon Ferguson, who led the state’s team as a deputy attorney general and now is a solo in Bainbridge Island, Washington, says Webb had a good way with the jury: “You’ll see some guys who come [into court] and do this affected hayseed routine. Dan is actually down-home. It’s not an act.” Ferguson says that instead of a seamless presentation, Webb often stopped and switched course in the middle of a question. “You almost get the feeling with Dan that you’re dealing with Columbo: ‘Wait a minute. There’s one thing I don’t understand.’ ” It was highly effective, remarks Ferguson, who says the jurors he talked to after trial really liked Webb. “ He was their favorite.”

In the upcoming Justice Department tobacco trial, Webb won’t be playing to a jury. The tobacco companies had asked for a jury trial, but Judge Kessler denied the request. She concluded that the relief sought by the government, including the disgorgement of profits, was equitable in nature and did not require a jury trial under the Seventh Amendment.

Judge Kessler has not been pleased with Webb’s client in recent months. In July she sanctioned Philip Morris $2.75 million for the “reckless disregard and gross indifference” it displayed when it deleted a mass of e-mails it should have turned over in discovery. Philip Morris maintained that the deletions were inadvertent, and stressed that the company had come forward to alert the judge about the problem. But Judge Kessler blamed Philip Morris for waiting four months after it discovered the problem in 2002 to tell her. The judge also punished the company by ruling that at least 11 Philip Morris witnesses, including one of its top in-house scientists, will be barred from testifying.

Despite Judge Kessler’s narrowing of the case, it remains a beast: More than 300 depositions have been taken, more than 200 witnesses are expected to testify, more than 600 pretrial orders have been entered, roughly 40 million pages of documents have been exchanged in discovery, and the two sides have designated more than 70,000 potential exhibits for trial. The trial is predicted to stretch into next year.

Webb tries to ease the toll of such lengthy stints away from home. During the year he spent in Miami on Engle, his five children, now 6 to 27, would fly in for occasional visits. “I’m very close to my kids. But I’m not there as much as I should be,” says Webb, who has been married once, for 32 years. He met his wife when she worked as a secretary at the U.S. attorney’s office. “My kids have been great about it,” he says. “But they think I work too hard.”

If Webb is enamored of the financial trappings of success, he’s managed to keep it a secret. The Winston & Strawn partner doesn’t keep a yacht on Lake Michigan, belong to a country club, or even have a second home. Webb’s secretary, Gail Wooten, laughs when asked if her boss lunches at fancy restaurants. “Normally he orders in,” says Wooten, who notes that Webb has a fondness for Popeyes fast food chicken. As for Webb’s hobbies, Wooten mentions one passion: “He has this pond [at his home] that he’s infatuated with. . . . It’s a beautiful pond with koi fish. That’s his baby. He’ll come back from a trip, and the first thing he’ll ask about is the pond. He’ll be calling me from the road asking about the pond.”

It’s an enthusiasm spurred by happy childhood memories. “When I was a kid, I loved ponds and fish and creeks,” explains Webb. “I was constantly trying to catch frogs and stuff.”

If you were Dan Webb, you would have spent your youth in the small town of Bushnell, Illinois, roughly 200 miles southwest of Chicago, where your father juggled jobs, including delivering mail and selling farm implements, while your mother worked as a dental assistant. Some small towns are quaint. Bushnell isn’t one of them. Today half of the fading downtown stores are boarded up. The rest are barely hanging on. The lone pharmacy, Glash Drugs, does not have enough merchandise to fill its shelves.

Webb and three of his children spent this past New Year’s Eve in Bushnell with his sister, Diane Hoyle, who still lives there. “We had a real good time,” says Hoyle. “We stayed home and played with the kids.” She describes how competitive her brother was as a child. “He liked to win at croquet and Monopoly and whatever,” she says. He was also extremely disciplined. “Mother and Dad would give us money to go to the show,” Hoyle says. “Danny would save his candy money. At the pool he would drink from the water fountain and save his money.” During high school summers, Webb earned a paycheck working in the Vaughan and Bushnell hammer factory, where he cleaned out boilers and painted the roof.

Webb was also prone to accidents. “He fell out of an apple tree when he was 7 or 8,” recalls Hoyle. “In high school he cut his toe off mowing at a nursing home. Then . . . my dad backed over him with a car and broke his leg. Dad felt bad about that.” The missing toe kept Webb out of the service during the Vietnam War. “I never saw it as a detriment,” says Webb matter-of-factly.

Webb kept a better footing in the classroom. “One guidance counselor tested him and said he was a real genius,” says his sister. That counselor introduced Webb to the possibility of a legal career by giving him a book about Clarence Darrow, which he still has. “We had to watch Perry Mason,” Hoyle adds. Her brother, she recalls, “ was just obsessed with that show.”

In high school Webb signed up for drama club and chorus and served as sophomore class treasurer and as a junior Rotarian. He also longed to see the world beyond Bushnell. A few times he snuck into Chicago with friends, lying to his parents that he was staying with his grandfather nearby. For college, he moved 15 miles away to Western Illinois University in Macomb. The school’s motto: “Endless Options, Zero Pretensions.”

When Webb moved to Chicago to attend Loyola University Chicago School of Law, his mother was appalled by the condition of his apartment. “There were three or four of them living there,” says Hoyle, “and Dan’s bed was in a closet. Mother was shocked and could not believe her son was living like that.” Webb was miserable at first-he didn’t know anyone and didn’t have any money. After one year he switched to night school and worked days at a bank supervising clerks who encoded checks.

Hoyle sounds amazed that her brother has become such a famous lawyer. “When I go to watch him in court, it’s like two different people,” she says. “At home he’s relaxed and wanting to play games or cards. It’s like pulling teeth to get him to talk about what he’s doing [at work].” When Webb comes back for visits, he and his sister still play croquet.

If you were Dan Webb, you would have spent much of January in Madison County, Illinois. You would have set up shop in the infamous plaintiffs haven in the southern part of the state to defend Wyeth in another fen-phen case. You would be going before the very same judge, circuit court judge Nicholas Byron, who ten months earlier imposed a $10 billion award in a bench trial against your client Philip Morris. That was a class action alleging that tobacco companies deceived the public about the dangers of “light” cigarettes. Although you didn’t try the case, your partners at Winston & Strawn were on the losing side. (The case is now on appeal before the state supreme court.)

On the day that jury selection is scheduled to begin, Webb studies papers in a binder. Judge Byron picks up a file and smashes a bug on his desk. After some preliminary matters, Webb approaches the bench. “Something extraordinary has happened,” Webb tells the judge. “[The plaintiffs] have pled a brand-new cause of action that is not in the original complaint.” Webb asks to postpone the trial, and the judge obliges. Instead of rushing off, Webb plants his arms on Judge Byron’s bench, and for a half hour the two trade war stories like old chums, even though they’d never met before. That evening, when Webb returns to his hotel by the interstate, he runs in circles around the hotel parking lot, in the freezing dark, to get some exercise.

The next day Webb and his staff pack boxes in a local office park suite. He’s wearing loose-fitting jeans and a turtleneck. “I was bummed out,” says Webb about the postponement. “You put these small armies together. There’s this intensity, your heart is pounding.” Fiddling with a supersize Starbuck’s coffee, Webb talks about what it takes to be a good trial lawyer: “You have to work and work and work and work harder than the other side.”

Three days later Webb is in Chicago federal district court for former governor Ryan’s criminal case. The judge suggests a trial date in early February 2005. Webb asks for March. “I’ll be finishing [the Justice Department tobacco trial] sometime later in January,” he explains. “To have a few weeks to get ready I think is a reasonable request.” The judge agrees.

Later that day, back in his corner office in the prestigious 35 West Wacker Drive skyscraper, Webb reveals what he dreads the most. “Easily my biggest fear in life is boredom,” he says. “I think the practice of law can by and large be pretty boring: pushing paper and dealing with abstract issues and constantly being bogged down with a mass of things to do with very little focus. At least when you’re on trial, you do not get bored. You’re living by hard work and your wits. . . . I tend to balance a lot of balls in the air. I do fear boredom. . . . In a small town, you have to go out of your way to stay occupied.”

In the weeks before the tobacco racketeering trial was set to begin, Webb found a way to stay occupied. He went to trial-representing Verizon Directories Corp. in a claim charging Yellow Book USA, Inc., with falsely advertising that it has the most popular phone directory. The Lanham Act case was tried without a jury before federal district court judge Jack Weinstein of the Eastern District of New York. At press time the case had not concluded.

“This year I have bounced from one trial site to another,” says Webb during a call from the Verizon trial site in Brooklyn. “This has been a fairly intense year. When I get this many cases bunched up, I can’t spend time with family and friends as much as I want. I can’t run as much as I want. But I can’t choreograph my life.”

You still want to be Dan Webb?

E-mail: sbeck@amlaw.com.