San Francisco 49ers: Ranking 5 worst head coaches over last 20 years

No. 3: 49ers Head Coach Mike Singletary

Years Coaching: 2008-2010

Win-Loss Record: 18-22

Like Mike Nolan, the coach he replaced, there was no shortage of buzz around the hiring of Hall of Famer Mike Singletary.

Singletary inherited Nolan’s job on the interim in 2008 and produced a 5-4 finish during the latter half of the year. When the Niners finished at the .500 mark the following season, which marked the first time they hadn’t finished below eight wins since 2002, it generated plenty of excitement and hype for 2010.

Instead, Singletary’s 49ers started off 2-6, and the subsequent 5-10 record ultimately led to his firing and one-game interim success of Jim Tomsula to round out the season.

Singletary’s press conferences, sideline antics (thank you, Vernon Davis) and reported locker room pants-dropping incident were all entertaining, at least from a discussion standpoint.

But some other talks of him being wholly underprepared for game days were troubling enough. One 49ers player later noted Singletary was the least-prepared coach for a game he had seen since his high school days.

Not a ringing endorsement, especially when Singletary was dismissed in May 2022 from Trinity Christian Academy-Addison high school after posting a 1-21 record.

At least San Francisco had enough talent to win some games with Singletary at the helm in 2008 and 2009.