Bennett's father, Ken Bennett, has been involved in Democratic Party politics on the local and national level. Ken Bennett worked for Barack Obama as a presidential appointee and as an aide. Ken Bennett also worked on Obama's presidential campaign in 2008, and has worked as an aide to Mayor of Chicago Rahm Emanuel and as 2019 Chicago mayoral campaign co-chair for Toni Preckwinkle. Despite his family's ties to the Democratic Party, Bennett has called himself an independent voter, though he has a history of supporting Democrats. Bennett volunteered with Barack Obama's reelection campaign by phonebanking in Hyde Park, Chicago and has given speeches at the University of Chicago Institute of Politics.