Top Gun Interview: Attorney Dan Webb

Earlier this summer, I interviewed one of America’s greatest trial lawyers, Dan Webb.

In May, I reached out and asked to interview him for my Successful Lawyer blog. He agreed, telling me he’d be available after he returned from his upcoming trial in Delaware. Little did I know at that time, the upcoming trial was the Fox and Dominion defamation case, where he was the lead trial counsel for Fox. He told me when we met that he was literally standing up to do his opening statement when he got the call that it settled. Whoa!

Webb, a partner at the Chicago Law Firm of Winston and Strawn, originally made his mark in the 1980s as a federal prosecutor overseeing the prosecution of corrupt officials in Cook County, Illinois. 92 were indicted, including 17 judges, 48 lawyers, eight policemen, 10 deputy sheriffs, eight court officials, and one state legislator. Nearly all were convicted, with most of the defendants pleading guilty. Through the heroic efforts of Webb, the FBI, U.S. Attorneys’ office, Cook County State’s Attorney and others, Cook County Courts were cleaned up.

Later Webb gained renown as the special prosecutor for the government in the Iran Contra prosecutions of Oliver North and John Poindexter. As his friend and retired Federal Judge Charles P. Kocoras wrote in his biography of Webb, May it Please the Court: A Story about One of America’s Greatest Trial Lawyers:

Webb had an unmatched record of success both as a government prosecutor and as a criminal defense lawyer; and was familiar with the pressures of being in the public eye and in a courtroom matched against worthy adversaries. Nothing he had done previously, however, would compare to the intensity and scrutiny of his work on the Poindexter case. Because of the nature of the case, its high profile in the public arena, and the prospect that a popular ex-president would be called as a witness for the defense, the idea that it would be the legal equivalent of the Super Bowl did not seem far-fetched.

I remember watching him cross examine President Reagan during the Poindexter trial. I was schooled by the deftness of Webb’s examination of this American icon. It was a remarkable feat of skill and finesse.

“Never slow down, never grow old…”

Tom Petty summed it up for me in his song Mary Jane’s Last Dance…“never slow down, never grow old”. I live my life according to that adage; Dan clearly personifies it as well.

We met at Dan’s office one morning in June. I first asked him what kept him going after all these years of practice. After all, he has accomplished about as much as any lawyer could possibly hope for. He responded that he considered himself an action junkie. He said he continues to love the courtroom and loves trying cases. Even at the age of 77, he stays active and typically runs 20-25 miles per week. When asked when he would stop working, he told me a story about an older friend, who, when asked the same question responded, “when the phone quit ringing." Dan’s phone is still ringing.

I asked him what he identified as his superpower. He told me it was his health and vigor; he is blessed with a very high energy level. Dan continues to work long days. He told me he arrives at the office very early in the morning and prefers working at the office rather than at home. During the early days of the pandemic, only he and the security guard at his office building at 35 Wacker were on site. Depending upon whether he is on trial, his days go well into the evening. He said as he starts to get close to trial, it's not unusual for he and his team to only get two hours of sleep while putting the final touches on their preparation. In a normal night, he sleeps four to five hours per night and says that he feels great with that amount of sleep (I wish!). He cited Edison who said he got more done with less sleep. What a gift for a trial lawyer.

Trial Preparation

Dan and I discussed his approach to preparing cases for trial, which he described as granular. He said he is always the most prepared lawyer in the courtroom. He masters all case facts, which can be arduous depending upon the complexity of the cases. He reads everything methodically. I asked him about reading the law to prepare, and he said that most of his time was spent with the facts because the law is simply not that complicated in most cases.

One can never underestimate how thorough preparation leads to success in the courtroom. From my vantage point, every hour of trial time requires ten hours of preparation. Industriousness combined with focus lead to great results, no matter what type of case you are trying.

Dan’s approach to trial advocacy reminds me of the inspiring quote by the great collegiate runner, Steve Prefontaine, “I’m going to work so that it’s a pure guts race at the end, and if it is, I am the only one who can win it…”

Openings

According to Dan, opening statements are underappreciated. “If you get the jury leaning in your direction from the opening statement, they will often stay on your side throughout the trial.” Kocoras, May it Please the Court 107 (2015). The same holds true for a bench trial.

When preparing his opening statements, Dan gets a draft from associates and takes it from there. He revises the opening many times before it is ready to go. He then reduces it to a one-page outline for presentation. Because he has been over at so many times, it appears as though he is giving it extemporaneously. Dan told me before he even had a job, he went to watch the great trial lawyer Edward Bennett Williams try a case in Chicago. He modeled his own practice on what he saw Williams do, which among other things, was to present his opening statement from memory. I likewise watched Gerry Spence try a case when I was a law student. Modeling the greats beats the classroom when learning how to try cases.

Trial Themes

When I asked him about developing his themes, he said that they would usually arise during the discovery phase of the case, but they really would become apparent when he was working on the opening statement. In large cases, he presented possible themes to jury consultants to determine their viability. He would discern which ones worked and pare down the themes so that by trial, he was ready to go with a winning story. For me, trial themes bump around in my head until the eve of trial and then they gel. This is a problem because by then, I need to do last minute editing to incorporate them.

Direct Examination

I asked him how he prepares his direct examination, and he said that he writes out all his questions with the answers and references any supplemental materials that he needs including pertinent exhibits, refreshing materials and other references to help the witness. He said he doesn't necessarily work directly from the written questions but keeps them at the podium as a reference.

Cross Examination

Dan relies less on notes during cross because he wants to train the witness. He does this through direct confrontation. He said that if he were constantly going back to his notes, it would weaken witness control. He told me one of the techniques that he uses in a jury trial is to turn his back to the witness and talk directly to the jury. This is a method both to control the witness and impress upon the jury the witness’s recalcitrance.

Dan told an interesting story of the time he was cross-examining Oliver North, who, to nobody’s surprise, was a difficult witness (think Colonel Jessup from “A Few Good Men”). Dan kept a box with impeachment materials by his podium and every time North hedged his answer, Dan would go to the box and pull out the document to impeach him. Ultimately, according to Dan, whenever he (Dan) turned to go to the box, North would give him the answer he wanted. As Dan observed, Oliver North became like a Pavlovian dog, who was hurt every time the box came out. Ultimately, all Dan had to do was to turn toward the box and North became a compliant witness to avoid that pain.

What I also remember about Dan from watching him cross examine President Reagan many years ago was his firm, but unfailing courtesy to the witness and the court. This reminds me of Terry McCarthy’s axiomatic belief that you always want to “look good” to your fact finder during any type of trial. Being an overbearing tyrannical bully rarely works.

Closing Argument

Again, like the opening statement, Dan appears to have memorized the argument, but works from notes. This appearance comes from numerous dry runs before the actual argument. He described closing argument as a conversation with the jury, like in someone's living room. He said jurors don't know what to do necessarily, and he would try to help them through using a plainspoken delivery in an informal manner. Like his contemporary (and friend) David Boies (also a Midwesterner), a plainspoken and conversational delivery persuades. Bombast has no place for these two extraordinary trial advocates. This same principle would apply whether one tries a case to a judge or jury. Simplicity sells!

Dan Webb: Divorce Lawyer?

Dan volunteered that he has handled two divorces in his career, one was when he first hung a shingle early in his career and he did a divorce where they “fought over everything" and he did it because at that time, they needed the money. It obviously was not something he loved doing. Years later he told me that Jack Welch, the GE chairman, asked him to assist on his divorce. Reluctantly Dan agreed and at first could not get certified pro hoc vice in Connecticut because the trial judge did not think he had enough divorce experience. He was put on the stand and examined about his experience as a trial lawyer. Ultimately the trial court relented. I bet the judge felt kind of foolish after Dan recounted his professional experience on the stand.

Mental Flexibility

It's important that trial lawyers have mental agility and an ability to improvise. He told a story about a trial involving a sports agent that was accused of some improprieties affecting the Big Ten. One of the adverse witnesses was the great coach Bo Schembechler from the University of Michigan. Dan had prepared a withering cross-examination of Coach Schembechler but when he went into the courtroom, he saw two jurors handing Schembechler pieces of paper seeking his autograph. He decided on the spot not to cross-examine him at all. Discretion clearly is the better part of valor.

Wrap Up

As we wrapped up our conversation, we talked a little bit about Clarence Darrow and Earl Rogers, who represented Darrow during his bribery trial in Los Angeles. He told me about a biography of Rogers written by his daughter, which was less than complementary to Mr. Darrow. As he said, Darrow is a legend to Chicago trial lawyers, but not necessarily the rest of the world. I have a great portrait of Darrow hanging in my pool room (a/k/a “the scary guy” according to my grandson, Miles). Obviously, I’m inspired by the greats.

My morning interviewing Dan Webb was a glimpse into what makes a great trial lawyer. Energy, focus, and flexibility to be sure, but there is that something else contributing to his greatness. Humility and attention to detail come to mind. During my career, I’ve noticed a common thread of the greats of our profession, whether it be lawyers or judges: the higher elevated their status, the more down to earth. Dan is that, and then some. I see why juries eat out of his hand. For more insights in the career of Dan Webb, check out Judge Kocoras’s revealing biography.