After graduating from Harvard University, he taught in public schools in both Appalacia and later Chicago's Wicker Park neighborhood.
[6] In 1987 (at the age 29), Eisendrath successfully ran to succeed the retiring Martin J. Oberman as alderman (city councilor) in Chicago's 43rd ward.
The race between him and attorney Robert Perkins was dubbed by observers as the "Battle of the Blue Bloods", as both young candidates came from wealthy and well-connected families.
[10] Eisendrath endorsed the ward redistricting map proposed by Mayor Richard M. Daley when it was put to a public vote via a 1992 referendum.
[11] Eisendrath ran in the 1990 Democratic primary election for the U.S. House of Representatives in Illinois's 9th congressional district, challenging longtime incumbent Sid Yates.
[citation needed] He later served as Vice President of Academic Affairs for Kendall College but resigned the position in 2007.
[18] Later in 2018, Eisendrath resigned as CEO after meeting his original goals stating "Not only did we stop the (Tribune) merger, we successfully relocated, rebranded, restructured”.