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In this episode, Michael Collins sits down with Dan Webb, Co-Executive Chairman of Winston & Strawn and one of the most accomplished trial lawyers in the United States.
Over a career spanning more than six decades, Dan has tried more than 100 jury cases, served as U.S. Attorney for the Northern District of Illinois, prosecuted high-profile public corruption matters, and represented some of the world's largest organizations in complex litigation.
Dan shares the pivotal moments that shaped his career, the mentors who changed his life, and the lessons he has learned from decades spent performing under pressure. The conversation explores preparation, leadership, communication, courtroom strategy, the role of artificial intelligence in modern litigation, and what it takes to remain competitive at the highest level for an entire career.
Dan also reflects on cross-examining President Ronald Reagan, the decision to decline representing President Donald Trump, and why he believes ego is the enemy of success.
Whether you're a business leader, investor, attorney, operator, or anyone interested in decision-making when the stakes are high, this conversation offers a rare look inside the mindset of one of America's premier trial lawyers.
Topics discussed:
• Building a career through mentorship and opportunity
• The mindset behind 100+ jury trials
• Why preparation remains the ultimate competitive advantage
• Trial lawyers as communicators and salespeople
• The role of AI in modern litigation
• Cross-examining President Ronald Reagan
• Leadership, longevity, and staying competitive at 80 years old
