On February 26, 2019, Lori Lightfoot was elected Mayor of Chicago. Her victory was both historic and surprising. When she announced her run, Lightfoot was relatively unknown and a political outsider. She is also female, African-America and an out-lesbian – in marked contrast with almost every past occupant of that coveted fifth floor office on Clark Street. Consider that, in its less than 200-year history, Chicago has had exactly one other female mayor (Jane Byrne), two African-American mayors (Harold Washington and Eugene Sawyer), and no publicly-declared LGBT mayors. There has certainly never been a mayor that checked all three boxes. Suffice it to say that few people took Lightfoot’s candidacy seriously when she first announced her run.