Spoilers
“The Contenders”

It is election night in Rome, Wisconsin and there is a surprise write-in candidate, Jill Brock.
Jill decided to join the race for mayor initially to try and get Mayor Pugen to agree to some projects that she wanted to get done. Jill decided she really wanted it.
This was a look on the world of politics, especially how the negativity can mess with people. The press brought up the fact that Jill and Jimmy had gotten together prior to Jimmy and his first wife, Lydia, had actually been legally separated. This brought up huge scars for Kimberly and we got some specifics of how this whole thing happened.

Meanwhile, Kenny arrests a man who was on the run from tax evasion who turned out to be a former pro boxer, “The Poet” Jeff Freed, played by Henry Brown. He was a hero to young Jimmy. Jimmy challenges the former champ to an exhibition boxing match to raise money for his defense. Jimmy was a former Gold Gloves boxer and wanted to face off with him. The relationship between Freed and Jimmy was strong through the episode.
Kenny is knocked out and Pugen wins re-election. Watching Douglas Wambaugh sadly leaving the boxing match after losing the election was devastating.
This is a perfect example of Picket fences. It takes the events and plot points to inform conflict among the characters, whether or not it makes the characters look bad. This is such a wonderful character piece.
