Fitzgerald worked in the newspaper business for nearly ten years, including as an owner. Fitzgerald was appointed Wisconsin Senate Majority Leader by his colleagues in 2011, continuing through the rest of his tenure as a state senator (except for a six-month period in 2012-13 as Minority Leader). In prior sessions, Fitzgerald served as Co-Chairman of the Joint Committee on Finance and Chairman of the Senate Corrections Committee. Fitzgerald received national attention in the wake of the 2018 Wisconsin state elections, when Democratic candidates were elected to the offices of governor, attorney general and secretary of state.