Born in Milwaukee, Wisconsin, Bennett grew up in the Twin Cities and received his Bachelor of Arts degree in political science and urban studies from Gustavus Adolphus College in 1972 and a Juris Doctor from Drake University Law School in 1975.

In a 2003 case, Judge Bennett was reversed three times by the United States Court of Appeals for the Eighth Circuit for considering post-sentencing rehabilitation when sentencing a defendant who had subsequently recovered from drug addiction and gained stable employment.

[7] In 2007, a divided Eighth Circuit, sitting en banc, reversed Judge Bennett after he refused to apply the 100:1 powder/crack cocaine sentencing disparity.

The Supreme Court granted certiorari and unanimously reversed the Eighth Circuit, holding that Judge Bennett could follow his preferred approach.

[1] After retiring from the federal judiciary, Bennett joined the faculty of Drake University Law School, where he is Director of the Institute for Justice Reform and Innovation.

[3] He has taught at law schools and hundreds of continuing education seminars in 41 states and publishes frequently in the areas of civil procedure and trial advocacy.