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Roosevelt has successfully overcome the odds throughout his career in order to pursue his dream of practicing law. He dropped out of high school at age 17 to join the United States Navy where he could gain the funds he needed to attend college. After service in the navy during the Persian Gulf War he completed his service time, gained further experience as a trooper in the Delaware State Police, and then attended Howard University, Delaware State University and the University of Wisconsin Law School. It was in law school that he had his first jury trials resulting in acquittals of his clients.


Roosevelt began his legal career in New York City, where he also taught as an adjunct professor at the John Jay College of Criminal Justice. He then ventured to Washington D.C. where he worked for the Office of General Counsel. He then opened his own law firm in Milwaukee, Wisconsin, where his practice focused on criminal and civil litigation.

In 2008, Roosevelt expanded his firm, opening an office in Chicago. In 2009, he became a partner in a larger firm dealing with plaintiff’s civil litigation. During those years he continued his trial litigation resulting in Multi-Million-dollar verdicts for his clients.

In 2016 he joined a Civil Litigation Defense firm specializing in defending insurers and self-insureds in matters of Catastrophic Loss, Professional Liability, Products and Construction Law, Trucking and Transportation.

After a brief stint on the Insurance Defense side, he rejoined Deratany & Kosner, concentrating on plaintiff’s personal injury.

Roosevelt is licensed in Illinois, Wisconsin and New York. He has extensive trial experience representing both plaintiffs and defendants.

Practice Areas

  • Personal Injury
  • Wrongful Death
  • Medical Malpractice
  • Police Brutality


  • Juris Doctor, University of Wisconsin Law School, Madison, WI, 2001
    • Honored for outstanding work in the Legal Defense Program representing indigent clients in criminal cases
  • Bachelor of Arts in History, Delaware State University, Dover, DE
    • Minor, Spanish
  • Attended Howard University, Washington, DC
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