Which One Chicago season had the worst villain?

Chicago PD: Denny Woods

BACKSTORY: Introduced during Chicago PD season 4 as Hank Voight’s former partner, Denny Woods (Mykelti Williamson) returned in season 5 with a single mission: to tear down Voight for nearly ruining his own career. He almost got away with it, too, except for some last-minute work by Voight and Assistant State’s Attorney James Osha (Michael McGrady).

MISDEEDS: As the longest-tenured bad guy on this list—the only one to span more than one season so far—Woods pulled off so many infuriating things that we needed a separate list of all his wrongs. If we only count what he was responsible for this season, he tried to lean on almost everyone in the Intelligence Unit, nearly got Woods and Alderman Ray Price (Wendell Pierce) shot, and set up all kinds of shady dealings while honestly believing he was morally superior.

VERDICT: Denny Woods has the longest rap sheet in One Chicago, solely because he appeared in one season 4 episode and then was in most of season 5 (as opposed to the other two contenders who were only in part of their respective seasons). His moral compass is irretrievably broken, and he has no problem creating innocent victims. The fact that he thinks he’s better than everyone is salt in the proverbial wound, too.

The show tried to humanize him by having Woods’ own daughter shot in “Anthem” but he still somehow managed to call that Voight’s fault, too. He’s worse than Grissom, but his time in One Chicago appears to be over since he was led away in handcuffs at the end of the season finale.