Attorney James D. Montgomery Jr. has the resources and legal insights you need to regain stability and look toward the future.
If you are facing a legal challenge, such as a civil right injustice or a serious personal injury caused by another, you have come to the right place. At Montgomery Law Firm LLC, we carry forward a legacy of excellence and compassionate representation of individuals and families in Chicago and throughout Illinois. Led by trial attorney James D. Montgomery Jr., our practice focuses on high-stakes cases that require careful investigation and intelligent strategy.
After decades practicing law in the corporate world and in private practice, Mr. Montgomery founded his own firm in 2015 to carry on the legacy of his father, James D. Montgomery Sr., one of Chicago’s most prominent civil rights and defense attorneys. Montgomery Law Firm LLC proudly brings that tradition of helping people stand up for their rights into the 21st Century with the unique insight of an attorney who grew up in the center of the civil rights movement of the 1960s and ‘70s.
In every case he brings to trial, Mr. Montgomery uses his “recipe for success,” a proven courtroom technique that tailors his courtroom approach to the best possible argument for persuading the 12 people in the jury box. He evaluates each matter with the expectation that it may need to be proven to a jury, not simply negotiated behind closed doors. That perspective influences how he investigates, develops, and presents cases from start to finish.
If you know or suspect you have grounds for a legal case, contact Montgomery Law Firm LLC today to get started with your initial consultation session. Our team will review your situation, address your concerns, and provide a straightforward overview of your options.
Montgomery Law Firm LLC handles plaintiff-side litigation for cases involving serious personal injuries, constitutional violations, and wrongful death. When people come to us for help, they receive our focused attention and personalized legal strategies based on the specific conduct involved and the impact it has had on their lives. Below is an overview of the types of legal matters we handle for clients across the Chicagoland area.
Protection After Your Civil
Rights Are Violated
Strong Advocacy for Accident
Victims and Their Families
Trusted Guidance After
a Motor Vehicle Accident
Montgomery Law Firm LLC represents individuals and families in cases involving serious injuries, civil rights violations, and wrongful death. Mr. Montgomery’s work focuses on claims against corporations, insurers, and government entities—opponents that often have substantial resources and institutional defenses working in their favor. These matters require thorough investigations, disciplined strategies, and deliberate preparation based on the real possibility of trial.
As an civil rights and injury lawyer, James Montgomery accepts only a limited number of cases so he can devote the appropriate level of time and attention to each matter. He evaluates every case he handles based on the facts, the available evidence, and the practical impact on his clients. Then, he develops litigation strategies with a deep understanding of how defendants assess risk and respond to pressure.
Our team emphasizes clear communication and adaptability. Mr. Montgomery works directly with clients to explain their options thoroughly and set realistic expectations. That way, they always know where things stand and can make informed decisions at each stage of the process.
At Montgomery Law Firm LLC, our practice is rooted in Chicago, and we take pride in serving our neighbors, particularly those who have been harmed by a local institution or public agency. Attorney Montgomery also represents clients in other parts of Illinois and beyond when jurisdiction and case circumstances allow. Regardless of where you’re located, Mr. Montgomery applies the same high level of preparation, communication, and trial readiness. He approaches each matter with careful attention to detail and respect for the personal impacts his clients have experienced, with a focus on helping people explore their options and make informed decisions.
At Montgomery Law Firm LLC, we approach each case as though trial is a likely outcome, not a remote possibility. Mr. Montgomery begins by examining how the incident unfolded, what evidence exists, and how he might be able to establish responsibility under the law. That early analysis shapes how he develops every case, from investigation and discovery through negotiation or trial.
Mr. Montgomery builds his strategies with a strong understanding of how institutional defendants like cities and police departments evaluate exposure to liability and make decisions accordingly. Mr. Montgomery’s background working inside corporate legal environments informs how he assesses risk, prepares witnesses, and frames issues for judges and juries. He uses this perspective to evaluate when to press forward, when to challenge assumptions, and when negotiation may make sense instead of trial.
Mr. Montgomery also prepares each case with jurors in mind. He evaluates how that panel of twelve individuals is likely to interpret the evidence, assess credibility, and assign responsibility. That perspective influences how he organizes facts, prepares witnesses, and presents arguments. By keeping his focus on how real jurors process information, Mr. Montgomery builds cases that are clear and effective at trial.
James D. Montgomery Jr. developed an early understanding of the law by watching his father practice in court. James D. Montgomery Sr. spent decades litigating some of the biggest civil rights cases during a formative period in U.S. legal history, and Mr. Montgomery spent his early years observing firsthand his father’s work advocating for equal rights for all.
While many of his peers only learned about civil rights law through later-in-life study, Mr. Montgomery saw how relevant cases were developed and argued long before going into practice himself. That early exposure played a role in his decision to pursue plaintiff-side civil litigation himself and influences how he practices law to this day.
Mr. Montgomery began his own career in civil litigation and has spent decades representing plaintiffs in civil rights, medical malpractice, personal injury, and wrongful death cases. He approaches each matter using his “recipe for success,” regarding juries, along with his credibility, and decades of experience. He centers his trial strategies on the specific facts of the case and the people affected, not standardized arguments.
Montgomery Law Firm LLC has handled a wide range of high-profile civil rights, personal injury, and wrongful death cases. While past outcomes are no guarantee of future results, the following examples of results the firm has achieved reflect the types of matters Mr. Montgomery has taken on and how they were resolved:
recovery for the family of Chequita Adams, who was killed when a high-speed police pursuit ended in a crash that killed Ms. Adams and an off-duty officer
in a federal court case involving a handcuffed detainee who suffered a concussion and facial fractures after a police sergeant struck him
for the estate of Jeffrey Lewis, a 17-year-old who was shot by police in Lake County under disputed circumstances
jury verdict for the estate of Aaron Harrison, an 18-year-old shot in the back by a Chicago police officer whose testimony was contradicted by civilian witnesses and forensic tests
