James D. Montgomery Jr.

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James D. Montgomery Jr.
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Mr. Montgomery Can Help You Through This Difficult Time.

James D. Montgomery Jr. is not just an attorney; he is a strategist, an economist, and a relentless advocate for civil justice. As the founder of Montgomery Law Firm LLC, he has secured millions of dollars in verdicts and settlements for his clients, earning a spot on the National Law Journal’s “Plaintiff’s Hot List” and the respect of the Chicago legal community.

From the Frontlines of History to the Ivy League

Born into the heart of Chicago’s civil rights movement, James grew up witnessing his father, legendary attorney James D. Montgomery Sr., fight some of the most consequential legal battles of the 20th century. This upbringing instilled in him a bone-deep understanding of justice and the courage required to confront authority.

However, James chose to sharpen his own distinct set of tools. He traveled west to Stanford University, where he earned a Bachelor of Science in Economics in 1979. There, he mastered the science of value, risk, and forecasting—skills he now uses to calculate damages and dismantle insurance company algorithms. He returned home to earn his Juris Doctor from the University of Illinois College of Law in 1982.

In a move that distinguishes him from nearly all his peers, James spent 17 years inside the corporate world. As an Attorney and Director of Operations for McDonald’s Corporation, he helped manage the safety, liability, and operations of one of the world’s largest companies.

He knows how corporations think because he was one of them. He understands the tension between profit and safety. He knows the “cost of doing business” calculations that companies make. Today, he uses that insider knowledge to expose negligence and hold corporations accountable when they choose profits over people.

In 2004, James returned to the courtroom, bringing his unique “hybrid” background to the service of victims. His results speak for themselves:

  • $8.5 Million Verdict for a victim of a police shooting (Johnson v. City of Chicago).
  • $6.5 Million Settlement in a complex commercial trucking wrongful death case (Estate of Kevetta Davis).
  • $5 Million Settlement for a bystander killed during a police pursuit (Estate of Chequita Adams).


James is a pillar of the Chicago community. He has served on the Board of Trustees for Loretto Hospital, fighting for health equity on the West Side. He is a member of the Illinois Trial Lawyers Association and maintains the family tradition of leadership within the Cook County Bar Association.

When you hire James D. Montgomery Jr., you are not just hiring a lawyer. You are hiring a Stanford economist to value your loss, a former corporate director to deconstruct the negligence, and a Montgomery to fight for your future.