[1] When he was 11, his father died in what was ruled a suicide, though later research by Maureen Hughes has indicated it could have been a murder.
[1] In 1984, Winchester ran for the Illinois Senate, but lost to Democratic candidate Glenn Poshard.
[3] In 1988, Winchester ran for his old seat against Democratic incumbent David D. Phelps and lost.
[5] In 1999, George Ryan hired Winchester to serve as his Deputy Chief of Staff overseeing the newly created Office of Southern Illinois.
[6] In the 2016 Republican Party presidential primaries, Winchester ran to be elected as a delegate to the 2016 Republican National Convention pledged to the presidential campaign of Florida Senator Marco Rubio.