Pedzisa mutsara unotevera: Pashure pokushanda somurongi womunda weDemocratic Party yeMichigan musarudzo yemutungamiri wenyika ya2000, uye ipapo pamushandirapamwe waJohn Kerry wemutungamiri wenyika muna 2004, Simon akabatana neBarack Obama's
nhimbe yapurezidhendi ya2008 somutungamiriri wezvokuongorora, anogara padzimbahwe reChicago. Sechikamu cheshambadziro iyi, akachengeta mashoko akawanda pamusoro pokuzvibata kwevavhoti uye zvavanofarira. Nzira yake yokunyatsoona vanhu vaanoda kuti vanyorwe nayo inonzi yakabatsira kuziva vavhoti vasina kusarudza vanganzi naObama vaite zvaanoda. Kutevera mushandirapamwe, akagadzwa muna 2009 kuti ashande muHurumende yaObama kuDhipatimendi reHutano neHuman Services, kwaakanangana nekugadziriswa kwehutano hwehutano uye Medicare.