[1] His grandfather Roger Isaac Wilson served as the Boone County sheriff, being killed in a shootout with bank robbers in 1933.

[2] His maternal grandfather, Ned Gibbs was also in politics, serving as Boone County recorder.

[1] Wilson began his political career as Boone County Collector in 1976, succeeding his late father.

[5][6] In 1992, he ran for Lieutenant Governor of Missouri, and won by a plurality against State Auditor Margaret B. Kelly.

[9] In 1995, Wilson served as the tie breaking vote, defeating a provision that would have enabled a referendum on concealed carry.

[12] However, owing to being significantly outraised by State Treasurer Bob Holden, and wanting to spend more time with his family, Wilson opted not run for Governor.

[14] In October 2000, on his way to a campaign event for U.S. Senate, Governor Mel Carnahan died in an airplane crash.

[18] McCaskill won the primary, but lost the general election to Republican Matt Blunt.