11th ward election
When Patrick Thompson, grandson of former Mayor Richard J. Daley, was elected 11th ward Alderman in 2015, media made a big deal about how the seat was now held by a member of the Daley family. But the real political news was that the guy had to compete in a runoff election to win the seat. Not since a Republican was elected in 1947 (allegedly with the help of Daley and some other Democrats) had the path to victory been less easy for the candidate of the Democratic Machine.