While attending the University of Pittsburgh, Wynn was initiated as a member of the Beta Epsilon chapter of Kappa Alpha Psi fraternity.

[citation needed] During the 105th Congress, Wynn sponsored legislation passed to improve federal contracting opportunities for small and minority businesses.

His 2000 re-election race made headlines, when the Congressman's estranged wife, Jessie Wynn, served as the campaign manager for his Republican opponent, John B. Kimble.

During the 107th Congress, Wynn was one of only four of 36 Congressional Black Caucus members who voted on October 10, 2002 for the joint resolution authorizing the Iraq War.

The other three Congressional Black Caucus members who voted for the resolution authorizing the Iraq War were Bill Jefferson of Louisiana, Sanford Bishop of Georgia, and Harold Ford, Jr. of Tennessee.

[3][4] Wynn also served on the Congressional Black Caucus' Political Action Committee and its Minority Business Task Force.

[2] Wynn has issued statements of support for integrating illegal aliens into society, so long as strong border security provisions are included.

[8][10] He became a partner of Dickstein Shapiro, a large lobbying firm whose clients include the tobacco, entertainment, energy, and software industries as well as the Teamsters.