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- From 2010 to 2020, Judge Jackson-Akiwumi was a Staff Attorney with the Federal Defender Program for the Northern District of Illinois.
- Judge Jackson-Akiwumi represented over 400 clients accused of federal crimes and supervised a team of legal professionals.
- Judge Jackson-Akiwumi argued half a dozen appeals in the U.S. Court of Appeals and filed petitions for writ of certiorari to the U.S. Supreme Court.
- Judge Jackson-Akiwumi served as an adjunct professor at Northwestern University’s Pritzker School of Law in 2018.
- After she was confirmed, Judge Jackson-Akiwumi became only the second Black judge to ever serve on the Seventh Circuit Court of Appeals, and the only non-white active judge on the court.