James D. Montgomery Jr. is the founding attorney of Montgomery Law Firm LLC, a Chicago trial-focused law firm that focuses on civil litigation involving serious injuries, civil rights violations, and wrongful death.
With Mr. Montgomery, you get a lawyer who spent his entire life in a courtroom watching his father, James D. Montgomery Sr., a legendary Chicago criminal defense and civil rights attorney, litigating some of the biggest civil rights cases in the 1960s and ‘70s. He emulates his father’s work by fighting for equal rights for all.
His approach reflects his background shaped by this early exposure to civil rights advocacy through his father and his decades of experience in litigating serious injuries to individuals and families throughout Chicagoland. Mr. Montgomery’s unique background growing up immersed in the law helps shape how he evaluates evidence, challenges official narratives, and presents cases to juries and judges.
If you have been harmed due to a civil rights violation or serious personal injury, contact Montgomery Law Firm LLC today to arrange your initial consultation and learn how we can help you.
Attorney Montgomery handles civil litigation matters involving civil rights violations, serious personal injuries, and wrongful deaths. Our firm centers on cases where the facts matter, the stakes are high, and careful trial preparation drives results. The matters we handle often involve institutional defendants, disputed records, and competing expert opinions – factors that can put everyday people at a serious disadvantage if they lack strong advocacy.
Our work includes civil rights claims against law enforcement, medical malpractice involving preventable harm, and injury cases arising from catastrophic events. Our attorney approaches each case with customized strategies rather than preset formulas. Using his proven “recipe for success” for jury trials, he develops a strategy based on the evidence, the applicable laws, and the individuals selected for the jury. He and the rest of our team can commit this kind of focus to each case because we intentionally accept only a limited number of cases.
James D. Montgomery Jr. earned his undergraduate degree in economics from Stanford University and his law degree from the University of Illinois College of Law. Before that, he grew up with front-row look at his father’s work using the law to help advance the civil rights movement of the 1960s and ‘70s. What many people could only read about in history books, Mr. Montgomery lived through.
Since becoming a lawyer himself, Mr. Montgomery has focused his practice on civil litigation since the start of his career, with an emphasis on cases involving systemic failures, professional negligence, and abuse of authority. We are passionate about helping ordinary people take on powerful institutions like law enforcement and City Hall and holding them accountable when they break the law and abuse civil rights. These vital rights include due process, equal protection before the law, and the right to privacy. Without the ability to enforce those rights in court, Americans aren’t free to live the lives they deserve.
Mr. Montgomery’s work on each case he accepts starts well before stepping into the courtroom. He evaluates each case at the intake stage and works hard to develop intelligent litigation strategies, prepare witnesses, and present cases to juries. Clients work directly with him throughout each stage of their cases. That structure allows Mr. Montgomery to adjust his approach based on the facts as they develop, rather than relying on assumptions from early on in the process. His results reflect his long-term experience in trial advocacy and an approach grounded in preparation, clarity, and discipline.
Mr. Montgomery’s legal background started early in his life. He grew up observing civil rights litigation firsthand through the work of his father, whose career included landmark criminal defense and civil rights cases in Chicago, and whose clients included the Blackstone Rangers and the Black Panthers. Courtrooms, case discussions, and trial strategies were part of the younger Mr. Montgomery’s everyday education long before law school.
That early exposure to the justice system shaped Mr. Montgomery’s understanding of the role of the courts and the essential function lawyers provide. While his practice differs from his father’s in many ways, that influence still shines through in his focus on accountability and procedural fairness. His perspective comes from lived experience, not retrospective study. It informs how he evaluates evidence, challenges institutional misconduct, and frames arguments for both judges and juries.
Mr. Montgomery approaches each case as a distinct problem to be solved. He does not rely on stock arguments or templated litigation plans. He knows how to evaluate jurors and tailor his courtroom style to present his client’s case in a way most likely to convince the jury. He brings his preparation early and continues to adapt as things shift during trial.
His courtroom style emphasizes clarity and credibility. He focuses his arguments on documented facts and cause-and-effect relationships. He prepares witnesses with an eye on accuracy and consistency rather than performance. Over time, his methods have proven highly effective in cases involving complex records and contested narratives. His goal is not volume or speed – it’s persuasion grounded in evidence. That approach reflects Mr. Montgomery’s years of trial experience and his commitment to presenting each case on its own terms.
Montgomery Law Firm LLC focuses on civil litigation for cases involving serious and fatal injuries and violations of people’s rights. Our principal trial lawyer handles cases that demand detailed investigation, expert analysis, and trial-ready preparation. These include cases that involve:
Mr. Montgomery represents clients injured in car, truck, motorcycle, and pedestrian accidents, as well as cases involving catastrophic injuries, defective products, FELA claims, and fatal incidents.
Before building his trial practice, James D. Montgomery Jr. spent seventeen years working for a major corporate legal department. In his role as a corporate attorney, he advised business leadership on risk, liability exposure, and operational decision-making. He also reviewed claims from the defense side and participated in evaluating when to litigate, when to settle, and how Chicago juries might respond to internal records and testimony.
That experience shapes how he approaches civil litigation today. Mr. Montgomery understands how large organizations document decisions, assess financial exposure, and manage public risk. When representing injured individuals, he applies that insight to his discovery, deposition, and trial strategies.
Trial lawyer James D. Montgomery Jr. has secured numerous significant verdicts and settlements that reflect his diligent, trial-ready approach. For example:
Mr. Montgomery’s peers have consistently recognized him for his work. He has been selected to Super Lawyers for the past fifteen years running, a designation awarded to only a limited percentage of attorneys in each state per year. He has also been named to The National Law Journal’s Plaintiff’s Hot List, an editorial distinction based on Mr. Montgomery’s litigation results and their impact. These recognitions reflect a career built on trial readiness, disciplined case development, and real results.
