Member Directory
Member Directory

James Montgomery, Sr.

James D. Montgomery & Associates, Ltd.
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James Montgomery, Sr.
James D. Montgomery & Associates, Ltd.

James D. Montgomery was born in Louise, Mississippi on February 17, 1932, and received a B.A. in Political Science from the University of Illinois in 1953. A 1956 graduate of the University of Illinois College of Law, Mr. Montgomery has extensive litigation experience in both state and federal court and has appeared in trials in various states throughout the country. He is admitted to practice before the United States Supreme Court and has also appeared before various United States Courts of Appeal and the Illinois Supreme Court to argue cases. His reputation as a skilled litigator is widely known, with respect to both criminal and civil-rights cases.

In 1956, Mr. Montgomery began his legal career with the law firm of Rogers, Strayhorn & Harth. He later became an Assistant United States Attorney for the Northern District of Illinois. His commitment to civil rights and his community led him to establish his own firm, James D. Montgomery & Associates, Ltd., where he became involved in several landmark civil rights cases including Hampton v. Hanrahan, a case where the Black Panther chairman, Fred Hampton and Rockford Black Panther leader Mark Clark were murdered during a Chicago police raid. After an 18 month trial and subsequent appeal, the case settled for 1.8 million dollars. In the 60s and 70s, Mr. Montgomery filed suits successfully challenging de-facto school segregation and disparate compensation paid to African-American Full Time Basis substitute teachers in the Chicago Public Schools. He developed his well-honed trial skills while trying hundreds of challenging criminal cases.

In 1983, Mr. Montgomery was appointed Corporation Counsel of the City of Chicago, under Mayor Harold Washington, where he supervised a legal staff which exceeded 190 lawyers. Also in 1983, he was named a fellow of the prestigious International Academy of Trial Lawyers which is by invitation only. He has served on numerous advisory groups and committees including The Civil Justice Expense and Delay Advisory Group for the United States District Court for the Northern District of Illinois and Judicial Evaluation Committees for the state and federal courts.

In January of 2000, Mr. Montgomery settled a case against an automobile manufacturer for a defective design of its roof structure for 9.8 million dollars. In 2001, he also settled a case against the City of Chicago for 18 million dollars on behalf of the Estate of LaTanya Haggerty, who was shot and killed by a Chicago police officer in June 1999. The settlement represents one of the highest awards in the history of the State of Illinois. Mr. Montgomery also settled the wrongful-death case of Rashidi Wheeer for 16 million. Wheeler was a Northwestern football player who died at an unauthorized football practice in August 2001. In 2006, Mr. Montgomery achieved a verdict for 23.5 million dollars in an auto negligence case and a verdict of 6.75 million in a malicious-prosecution case.

In addition to his professional activities, Mr. Montgomery is a frequent lecturer in various seminars and trial skills workshops. He taught a trial advocacy class at DePaul University Law School and trial skills workshops for the National College of Criminal Defense Lawyers. He participates in a week-long Trial Advocacy workshop at Harvard Law School in Cambridge and teaches an Intensive Trial Practice Course at the University of Chicago Law School for its Intensive Trial Practice Workshop.

In March of 2001, Mr. Montgomery teamed up with the prestigious Johnnie L. Cochran, Jr. The Chicago press has referred to Mr. Montgomery and Mr. Cochran as the "Dynamic Duo".

In 1999, The Illinois Academy of Lawyers inducted Mr. Montgomery as a "Laureate" in the Academy. As described in the bylaws of the Academy, a Laureate must "personify the greatness of the legal profession and help to establish and maintain its highest principles through a pervasive record of service to the law, the profession and to the public" and that truly describes Jim.

Mr. Montgomery currently serves as a trustee to the University of Illinois Board of Trustees.

He is married to Pauline and has 6 adult children: Linda, James, Jr., Michelle, Lisa, Jewel and Jilian. He also has three grandchildren: Gemilyn, Lindsey and Stella.

Areas of Practice

  • Catastrophic Personal Injury
  • Wrongful Death
  • Personal Injury
  • Medical Malpractice

Litigation Percentage

  • 95% of Practice Devoted to Litigation

Bar Admissions

  • Illinois, 1956
  • U.S. Court of Appeals 7th Circuit, 1960
  • U.S. District Court Northern District of Illinois, 1957
  • U.S. Supreme Court


  • University of Illinois College of Law, Champaign, Illinois
    • J.D. - 1956
  • University of Illinois, Champaign-Urbana, Illinois
    • B.A. - 1953
    • Major: Political Science

Representative Cases

  • Hampton v. Hanrahan


  • Instructor- Trial Techniques, University of Chicago Law School, 2000 - 2012
  • Instructor- Trial Techniques, National Association of Criminal Defense lawyers, 1975 - 1982
  • Intensive Trial Practice Course, University of Chicago Law School

Honors and Awards

  • Fellow, Prestigious International Academy of Trial Lawyers, 1983
  • Laureate, Illinois Academy of Trial Lawyers
  • Honorary Fellow, Illinois Bar Foundation, 2010 - Present

Professional Associations and Memberships

  • American Board of Trial Advocates, Associate, 1993 - Present
  • International Academy of Trial Lawyers, Member of the Board of Directors, 1983 - Present

Past Employment Positions

  • City of Chicago, Corporation Counsel, 1983 - 1987

Pro Bono Activities

  • Trustee, University of Illinois, 2006 - Present
  • Board Member, Loretto Hospital, 2010 - Present

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