Rubuta ci gaba don wannan sakin layi - Bayan aiki a matsayin mai shirya filin don Jam'iyyar Democrat ta Michigan a zaben shugaban kasa na 2000, sannan a yakin neman zaben John Kerry na shugaban kasa a 2004, Simon ya shiga yakin neman zaben Barack Obama na 2008
a matsayin darektan bincike, wanda ke da hedikwata a Chicago. A wani bangare na wannan yakin, ya gudanar da adana bayanai game da halayyar masu jefa kuri'a da abubuwan da suke so. An yaba da dabarun sa na daidaitaccen manufa tare da taimakawa wajen gano masu jefa kuri'a waɗanda ba su yanke shawara ba waɗanda Obama zai iya yin sujada. Bayan yakin neman zabe, an nada shi a shekarar 2009 don yin aiki a Gwamnatin Obama a Ma'aikatar Lafiya da Ayyukan Dan Adam, inda ya mai da hankali kan gyaran kiwon lafiya da Medicare.