Regret No. 2: Retaining J.B. Bickerstaff
This is a complicated and controversial situation, and it's certainly not clear-cut that the Cavaliers made a mistake. What is clear is that the Cleveland front office and owner Dan Gilbert elected to keep head coach J.B. Bickerstaff after a dismal playoff exit. The thought process was that Bickerstaff was an excellent culture-builder, that the playoff loss was more about the roster and lack of experience than it was about the coaching.
20 games into this season, it appears that while Bickerstaff may not have been the problem (or at least the sole problem) he doesn't appear to be the answer, either. The Cavaliers look like a team struggling with their identity, and while experimenting with different offensive and defensive schemes is valuable, the Cavs look more like a team that doesn't know what it is.
Are they a pick-and-roll heavy offense, with Jarrett Allen and Evan Mobley barreling into the paint as they roll to the rim? Are they a motion offense, with the bigs at the elbows handing off to sprinting shooters? Are they a heliocentric offense that needs to get out of the way and let Donovan Mitchell cook? If the on-court product looks uncertain, the coach is the first place to look for answers.
It's possible that Bickerstaff is the steady hand on the rudder that leads them out of this early-season malaise and into a Top-4 seed in the East and a playoff series win. It's also very possible that he has a ceiling as a coach, the kind of culture-builder that is ideal for turning a rebuilding team into a playoff team but isn't the kind of innovative mind to excel in the playoffs. That's a theory we've been exploring around here for quite some time.
Firing Bickerstaff during the season is on the table, but it's not without its issues. The Cavaliers did succeed firing a coach in-season before when Ty Lue stepped in for David Blatt and led the team to a championship, but generally a coach needs a full offseason to install their system and get the right kinds of role players on the roster. Firing Bickerstaff now is a panic move; firing him this past offseason would have been an upside play for the future.