
27. Mike Singletary
Some people argue who was worse out of Singletary and Jim Tomsula. In truth, it’s probably a case of pick your poison. The former had a losing team who won as soon as he left. But it’s a case of vice-versa for the latter. Overall, the confrontational and aggressive Singletary was terrible for the 49ers. He somehow lingered in San Francisco for three seasons, but they were as tepid as bog water.

His players felt alienated and frustrated by his field-side shtick. In his second season, the 49ers went 8-8, but that was the highlight of his career there. Otherwise, he managed just five wins per season. To sum up, he was very bad and didn’t have a ground of understanding with his squad in the end. Not every Hall of Famer also ends up a great coach.