The Academy Awards only honor Best Directors, but we are going to acknowledge the worst directors: the coaches who made the worst decisions in the sports year.
Craig Counsell: Facing the platoon-heavy Los Angeles Dodgers in the NLCS, Milwaukee Brewers manager Craig Counsell tried to exploit this by announcing a fake starter for Game 5. He had left-hander Wade Miley start, who walked the first batter and was immediately replaced by a right-handed reliever. But having replaced his starter after one batter, Counsell then left his reliever in way too long, and the Brewers had nothing to show for their chicanery but a 3-2 series deficit.
Frank Reich: Colts coach Frank Reich went for it on 4th down, with time running down in overtime, and did not get it. There was very little upside to the gambit, with the Colts in their own territory, and the effect was to essentially handed the rival Houston Texans their first victory. They might have fired their coach; instead, Houston won the division.
Jon Gruden, generally: Jon Gruden got a ten-year contract to coach the Raiders, and proceeded to trade the team's best defensive player, All-Pro Khalil Mack, and then go 4-12. The Raiders got outscored by a whopping 177 points on the season, and Gruden has roughly $90 million left on his deal.
Winner: Jim Boylen: Jim Boylen took over for Fred Hoiberg for the Chicago Bulls, and immediately became a tyrant. Players had to run wind sprints during two-hour-plus practices, sat through endless film reviews, and were benched en masse by Boylen twice in one game. Within a week, he'd caused a near-revolt, the team was booed off the court twice, and Boylen was scrambling by forming a player "leadership committee." He is currently 9-25 as a head coach.