Very, very few things scream “Chicago sports fan” quite as much as the unearned self-confidence to believe we could do a better job as head coach whenever our favorite teams make a misstep. It doesn’t even matter what sport it is — basketball, football, baseball, hockey, you name it, and we’re more than likely coming for the head coach’s job. The Chicago Bulls are a particularly interesting example in that regard, as they’ve been blessed with some of the greatest coaches in NBA history, but also cursed with a few of the worst.
So when a controversial figure like Billy Donovan strolls into town, you can bet there’s going to be an endless debate amongst the fanbase regarding his job performance. Donovan has posted a middling 117-119 record since taking over the team, which isn’t enough to wow, but is still quite respectable when you consider that he now ranks sixth all-time in total wins as head coach for this team.
Although Donovan isn’t the best coach we’ve ever had run the show here in the Windy City, he also certainly isn’t the worst. If you’re one of the misguided fans who think Billy is the sole root of Chicago’s struggles, I think it’s time we take a trip down memory lane to make it clear just how bad (and good!) it can really get when it comes to Bulls head coaches.
Through the highs and the lows, these are the 3 best and worst head coaches in Chicago Bulls history.
No. 3 worst: Bill Cartwright (2002-2004)
As a player, Bill Cartwright gave Bulls fans many happy memories as an integral piece to Chicago’s first three-peat championship run alongside Michael Jordan. As a coach, however, things did not go nearly as smoothly for Cartwright.
Taking the reigns for the Bulls in the post-Jordan era, Cartwright failed to help right the ship and posted a horrid 51-100 record as head coach. Cartwright was so bad that even his star player, Jalen Rose, would be traded for a poor package to the Clippers just to rid themselves of this terrible era of Bulls basketball.
Just one year after finishing 23-59 in the final season with Cartwright, Chicago would immediately return to relevance with a 47-35 record under new head coach Scott Skiles.
No. 3 best: Dick Motta (1969-1976)
Although Dick Motta’s time in Chicago came far too long ago for most Bulls fans these days to remember, his achievements should still not be diminished or dismissed in the slightest. Motta’s teams won an incredible 356 games, the second-most of any coach in franchise history.
Motta’s teams were littered with legends of the past including Chet Walker, Jerry Sloan, Bob Love, and Norm Van Lier. Although Motta was a first-time head coach and just the second coach to ever lead the Bulls after joining the NBA in 1966, he’d post a 54.3% winning percentage (the fourth-highest in franchise history) across eight seasons with the team. After leaving the Bulls, Motta would carry on to coach for 17 more seasons and even won a championship with the Washington Bullets in 1978.
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.
No. 1 worst: Tim Floyd (1999-2002)
If you thought Jim Boylen was a bad coach, I just pray you weren’t around to remember the Tim Floyd era in Chicago. Floyd coached 239 games for the Bulls from 1999 to 2002, and only managed to win 49 times. Yes, you heard that correctly. Floyd’s embarrassing 20.5% win percentage is by far the worst in Bulls history. As bad as Boylen was, he would have achieved 49 wins in 138 fewer games than Floyd did.
In the aftermath of the post-Jordan years, the Bulls were never going to be great. They certainly didn’t need to be downright horrible, however, as Floyd mismanaged and wasted great young talents such as Elton Brand, Ron Mercer, and Ron Artest.
I’m not sure what’s more mind-blowing here, the fact that Floyd was allowed to continue coaching the Bulls for four whole seasons, or the fact that he actually got another head coaching job in New Orleans following his release from the team. Unfortunately, Cartwright would take over for Floyd, so Bulls fans were in for another few rough years following his firing.
Phil Jackson transcended being just a Chicago Bulls legend and went down as one of the greatest head coaches in NBA history.
No. 1 best: Phil Jackson (1990-1998)
There was never any debate about who would lock down the top spot here, was there? Already having two championship rings to his name as a player, Phil Jackson would go on to have the greatest coaching career in NBA history, earning him the nickname of ‘The Zen Master’ as he helped pioneer The Triangle offensive scheme and steer the Chicago Bulls to becoming one of the most dominant teams in NBA history.
Jackson posted an incredibly 545-193 record as head coach for the Bulls, which puts him at No. 1 in franchise history for both total wins and win percentage. After winning six championships in eight years with the Bulls, Jackson would continue on to rack up seven NBA Finals appearances with the Lakers. Not only is Jackson the greatest coach in Chicago Bulls history, he’s arguably the best to ever do it. For any NBA team. Ever.