Fleming received a Bachelor of Arts from Kent State University in 1986 and a Juris Doctor from Case Western Reserve University Law School in 1990.

President Biden nominated Fleming to the seat vacated by Judge James S. Gwin, who assumed senior status on January 31, 2021.

[3] On November 17, 2021, a hearing on his nomination was held before the Senate Judiciary Committee.

[4] During his confirmation hearing, Fleming was questioned by Republican senators over the clients that he represented during his tenure as an assistant federal public defender, who included individuals charged with child pornography and impregnating a child.

[6][7] On January 3, 2022, his nomination was returned to the President under Rule XXXI, Paragraph 6 of the United States Senate;[7] he was renominated the same day.