No. 2 worst: Jim Boylen (2019-2020)
Although several years have already passed since Jim Boylen held down the head coach position for the Chicago Bulls, the stench of his tenure lingers around the franchise to this day. His strange antics and locker room feuds held the team back from reaching its full potential, and he ultimately ended up being the final straw that got former management duo John Paxson and Gar Forman fired.
Boylen’s teams went a disgraceful 39-84, a 31.7% winning percentage that ranks out as the second-lowest in franchise history. Boylen also had a penchant for calling seemingly intentionally frustrating timeouts, resulting in boos from opposing fans, denied points to Bulls players, and even his own star player Zach LaVine to curse him out.
Boylen is often attributed with holding back the development of future All-Star Lauri Markkanen, who would go on to have great success after being traded away by the Bulls. The Bulls have still yet to climb out of the pit of mediocrity since those days, but at the very least, we don’t have to see Boylen on the sidelines anymore.
Although Jim Boylen was an awful head coach, Tom Thibodeau’s greatness was enough to outshine those bad Bulls memories.
No. 2 best: Tom Thibodeau (2011-2015)
Few head coaches in Chicago pro sports history evoke the type of warm fuzzy nostalgia the way Tom Thibodeau does. In many ways, no head coach exemplified the gritty, hard-working side of Chicago as well as Thibs did, and it’s clear to see that this team has lost that piece of itself in the time since he’s been gone.
Although Thibodeau has carried on to find success with the Knicks, those Bulls teams continue to be the highlight of his coaching career. He posted a 255-139 record with the team, good for the third-most wins and the second-best winning percentage in franchise history. More importantly, he set the stage for what would become one of the most important eras of Chicago basketball, as Derrick Rose, Joakim Noah, Luol Deng, Jimmy Butler, and Taj Gibson all came together to set the standard for how this franchise should play.
Until another coach comes along and gets this team playing at a true championship contender caliber, I don’t think any of us will be taking off the rose-tinted glasses any time soon. And even if we do, that won’t change the fact that Thibodeau is the second-best coach in Bulls history.