Complex sentence: In 1996, Flanagan was soundly defeated by Democrat Rod Blagojevich, though both the Chicago Sun-Times and the Chicago Tribune endorsed Flanagan, and lost one of the eight seats first-term Republican candidates lost in the 1996 election.
Split into simpler sentences: In 1996, Flanagan was soundly defeated by Democrat Rod Blagojevich, though both the Chicago Sun-Times and the Chicago Tribune endorsed Flanagan. His loss was one of the eight seats first-term Republican candidates lost in the 1996 election.