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IL / Chicago

L. Michael  Flanagan

James D. Montgomery & Associates, Ltd.
33 West Monroe St, Suite 1375 
Chicago , IL 60603


L. Michael Flanagan joined James D. Montgomery & Associates as a lawyer in 2020. He practices in all areas of personal injury law. Prior to joining the Montgomery team, he was an associate at Corboy & Demetrio, P.C. Prior to joining Corboy & Demetrio, Michael was the principal of Flanagan Injury Law Group, LLC., a plaintiff’s personal injury firm. Since beginning his practice, Mr. Flanagan has garnered millions of dollars for his clients and was named a 2020 Rising Star by Super Lawyers, a distinction awarded to only 2.5% of lawyer under 40 in the State of Illinois.


In 2014, Michael held the position of law clerk for the Honorable Matthew Kennelly in the United States District Court for the Northern District of Illinois where he assisted the court with numerous jury trials. Simultaneously, he was also awarded a prestigious fellowship as a law clerk in the Cook County Bureau of Finance where he assisted in drafting contracts and advanced legislation. As a law clerk, Michael garnered extensive experience in every step of the personal injury litigation process including drafting motions and second-chairing personal injury arbitrations and trials. Michael attended law school at Loyola University Chicago School of Law where he began his extensive studies of personal injury matters and was deeply involved in the National Black Law Students Association and the Sports and Entertainment Law Society. He also spent significant time in China as part of Loyola University Chicago School of Law’s study abroad program.


Prior to law school, Michael honed his communication and client relations skills as a salesman at several top Chicago radio stations. Michael is a 2005 graduate of Howard University in Washington D.C., where he led students as Vice-President of the NAACP, was a legislative intern on Capitol Hill, and was published in numerous publications including Sports Illustrated On Campus while serving as the Assistant Sports Editor of the school newspaper. As a native Chicagoan, Michael remains deeply involved in his community as a member of the Apostolic Church of God and Union Lodge 155 PHA, Free and Accepted Masons. In 2019, Michael was appointed to serve on the Board of Directors of the Cook County Bar Association, the oldest bar association of African-American lawyers in the country. He is a member of the National Bar Association, Chicago Bar Association, Illinois Trial Lawyers Association and American Association for Justice.



Illinois Super Lawyers Rising Star

National Black Trial Lawyers Top 40 Under 40

Appointed to the Board of Directors of the Cook County Bar Association

Appointed to Illinois Prince Hall Masons Legal Committee for the Grand Lodge of the State of Illinois,


Nelson Mandela Pre-Law Scholarship Recipient



Cook County Bar Association

American Association for Justice

Chicago Bar Association

Illinois Trial Lawyers Association

National Bar Association



Chicago Bar Association Juvenile Mentoring Initiative Program Mentor

Tutor, Minority Legal Education Resources (MLER)



Construction Accidents

Medical Devices

Medical Malpractice



Hon. Matthew Kennelly, U.S. District Court for Northern District of Illinois, 2014


Loyola University Chicago School of Law, J.D.,

Howard University, B.A.,



State of Illinois

U.S. District Court, Northern District of Illinois

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