Chauncey Billups, Portland Trail Blazers
As the Portland Trail Blazers head into what will be year 2 of their rebuild, it may not seem fair to include Chauncey Billups on this list. However, considering he's heading into year 4, the team has to know pretty soon whether he's the head coach who's going to successfully lead this franchise into the future. Through three seasons, I'm not sure if the Blazers know that for sure either way. That's why heading into this season, if the Blazers don't take a big step forward in their development, there's an outside chance Billups could be the fall man.
In three years as the head coach, Billups has had no winning seasons, no playoff appearances, and has not led the team to more than 33 wins in any season. That's not ideal and in the NBA, coaches don't usually last four years without any steady improvement. That's the biggest reason why Billups' job could be on the line this season - even more so considering he's entering the final guaranteed year as the head coach of the Blazers.
If the Blazers don't take a significant step forward in their progression as a team, it would be surprising to see the Blazers extend Billups' contract.