It came as little surprise to anyone who has closely followed the Bulls since Dec. 3, 2018, when Boylen was named the team’s new head coach after Fred Hoiberg was fired. Since taking over, Boylen compiled a 39-84 record, with his .317 winning percentage representing the second-worst mark in franchise history.
From a reporter’s perspective, Boylen was a riot throughout his entire tenure. His stubborn, old-school approach led to tension in his locker room in the player empowerment era, and Boylen had such conviction in himself and his methods that there was rarely a probing question that he would sidestep.
With that in mind, let’s take a look back at some of the most bizarre moments and quotes from Boylen’s tenure. This is a long list, but we aren’t claiming that it’s comprehensive. So forgive us if we forgot a few and feel free to let us know.
In Boylen’s third game leading the Bulls, they were shellacked 133-77 by the Celtics at the United Center. The 56-point loss was and remains the worst in the history of the franchise, which began in 1966. Twice in the embarrassment, Boylen yanked all of his five starters at the same time hockey style, a sight rarely seen in the NBA. The second time he did it, he pulled the first unit at the 9:02 mark of the third quarter after the Celtics had opened the second half on a 5-3 run.
Boylen’s postgame news conference then produced an array of verbal gems.
"I play them more, we lose tonight and can't practice tomorrow, we double-lose," Boylen said of why his starters didn’t play for the final 21:02.
Asked whether he thought he embarrassed his Bulls starters with his tactics, Boylen fired back passionately.
"I think your play is embarrassing," he said. "Me subbing them is saving them, maybe. Maybe we saved them."
After that franchise-worst loss, Boylen called for the Bulls to practice on a Sunday after a back-to-back set of games, which is nearly unheard of in the NBA. Upon hearing that, a couple players took issue with the plan, starting a text message thread suggesting to teammates that the Bulls should boycott the practice. Bulls players went as far as to reach out to their union leadership about the situation. Cooler heads prevailed, and the Bulls instead held a lengthy meeting in which they aired their grievances.
Boylen contended that he planned all along to have the Bulls only do light work and that he wanted to use that tactic to help build trust with his players. Then he used a war reference.
"There’s been a little shock and awe here," Boylen said. "That’s the way I felt it needed to happen. First impressions last a lifetime. I don’t think anyone in here thought we were going to ease into this thing. That’s not my personality. That’s not how you effect change."
While on their way back to the locker room after a 108-89 win at the United Center, Kings players taunted the Bulls.
"Uh oh, another 2 1/2-hour practice for them tomorrow," a Kings player yelled, according to the Sun-Times.
In an effort to get on the same page with his Bulls and avoid future uprisings, Boylen formed a player leadership committee.
"I’m juiced, man," Boylen said. "I’m jacked about it."
Zach LaVine, Lauri Markkanen, Robin Lopez, Justin Holiday and Bobby Portis – basically the Bulls’ five best players at the time – were the original committee members. After Holiday and Portis exited and Otto Porter Jr. joined the Bulls amid a flurry of trade activity, Porter joined the committee.
While there were rumors that Kris Dunn would join the committee, he chose not to, the Sun-Times reported.
Asked about whether he needed to evolve to connect with the modern player better and help the Bulls become more of a free-agent destination, Boylen played the if-they-don’t-like-our-style-we-don’t-want-them card.
"If we are looking at free agents that don't want to work for or play for a competitive coach with great experience that is going to push them, then I don't know -- are we maybe targeting the wrong guys?" Boylen said on the Mully & Haugh Show. "We want guys who are going to come in and honor what the Bulls legacy is -- tough defense, competitive people and play the right way."
Trying to keep pace with a far superior Bucks team, Boylen and the Bulls ran out of timeouts with 6:51 remaining in the fourth quarter of a 112-99 loss.
Reflecting on the Bulls’ 56-point loss to the Celtics ahead of another game against Boston, Boylen offered some words of wisdom.
"My job is to prepare the child for the road, not the road for the child," Boylen said. "These guys are men. I’m trying to prepare them for the road."
Boylen and Clippers coach Doc Rivers were simultaneously ejected for yelling at each other in the third quarter of Los Angeles’ win against Chicago. Their feud began in the first half, when Boylen took issue with what he thought was a dirty screen from the Clippers’ Montrezl Harrell.
In an NBA coaching community that’s highly supportive of one another, Boylen recorded a rare feat. He upset a second coaching peer in the span of four nights.
Prior to the start of Bulls training camp, Boylen ordered a time clock and had it installed at the team’s practice facility, according to the Athletic. It signified the blue-collar culture Boylen wanted to create, and he literally had his players clock in.
"When guys come through the doors, they punch in now," Boylen said. "Punching in to work."
The Bulls entered the fourth quarter with a 13-point lead against the Lakers before melting down while Boylen just observed.
The Lakers ripped off a 16-0 run to open the final quarter, and it all came against five Bulls reserves as Boylen refused to substitute or call a timeout. When Boylen finally did call a timeout to stop the bleeding, it was too late as Los Angeles rolled to a comeback win.
"Nope," Boylen said when asked if he regretted not turning to his starters sooner. "Because I’m going to develop this bench and I’m going to develop this team. I’ve got 15 guys to develop."
Boylen then offered an explanation that contradicted the mass substitutions that he called for in his first week on the job.
"I’ve never yanked guys," Boylen claimed. "I’ve never done that, you know. I’m not doing that. We’re going develop that second group, and we’re going to have a bench here in Chicago."
Boylen also had a line for the ages when asked specifically why he didn’t use one of the four timeouts that he had left as the Lakers went on the game-changing run.
"I could’ve used one and didn’t," he said. "It was on my heart. It was on my mind."
With the Bulls off to a woeful 4-10 start against a rather soft schedule, Boylen admitted to "frustration" in a pregame interview and was asked what he needs to do better himself. He cited energy and then expressed conviction in his leadership style.
"I think the team needs who I am," Boylen said.
With the Bulls trailing 13-0 against the Heat, Boylen yanked LaVine – and LaVine alone – at the 8:33 mark of the first quarter. Boylen would later explain he did so because of "three egregious defensive mistakes," but it didn’t sit well with LaVine, who said, "I guess that’s just his thing to do."
"Zach LaVine got 13 points scored on him, I guess," LaVine continued. "Or was it the starting five? I don’t remember."
Two nights prior, forward Chandler Hutchison was active after recovering from his latest injury but didn't play. Boylen was asked why Hutchison didn't play, with the reporter wondering if it was because Hutchison didn't have a full practice under his belt yet since recovering.
"He didn't play because I didn't put him in," Boylen responded.
After Chicago’s 107-103 loss at Portland dropped the Bulls to 6-12, Boylen was asked what made him believe that wins would be coming in the future.
"If you build it, they will come," he responded. "You ever seen that movie?"
Boylen referenced his beloved "growth plate" following the Bulls’ 93-92 home loss to the Raptors, then shared another of his coaching beliefs.
"They brought their guys in, and they closed the game out," Boylen said. "We have to learn to do that. That’s the growth plate. We’re close. We’re right there. That’s the next step."
How do you know your team can take the next step?
"I coach by faith," Boylen responded.
After the Bulls routed the Hawks for an easy win, Boylen again referenced one of the goals he set for his team -- to average 35 assists per game. If it seemed ambitous, it's because it was. The NBA record for most assists per game is 31.4 by the 1985 Lakers.
Athletic reporter Darnell Mayberry pressed Boylen on the topic, wondering how he came up with that number for a Bulls team that often didn't even make 35 field goals per game.
"I watch the films," Boylen said. "I see the open shots we miss. I see the assists we have. I didn't pull this number out of thin air. This is something that I think we can do. I think it's attainable. I think it's a statement to how we want to play. If we don't get 35 and we get 30, that's still pretty good."
The Bulls ended up averaging 23.2 assists per game for the season, which ranked 23rd in the NBA. The Suns led the NBA with 27.2 assists per game.
At long last, the Bulls recorded their first victory of the season against a winning team by defeating the shorthanded Clippers, 109-106. Playing its third game in four nights to close a long road trip, Los Angeles played without Kawhi Leonard, Lou Williams and Patrick Beverly.
Chicago played without the less heralded and less accomplished trio of Otto Porter Jr., Chandler Hutchison and Daniel Gafford, a fact Boylen was quick to point out as he made an attrition comparison.
"Well, we didn’t have (Otto) or Hutch or Gafford," Boylen said. "So we can ‘yeah, but’ it a little bit too."
Continuing a theme, Boylen mismanaged his timeouts, and it burned the Bulls late in a loss to the Thunder.
With 33.1 seconds left in the third quarter, Boylen called a timeout with the Bulls leading by 10. It was a questionable decision, because the quarter break was coming one possession later and the play that followed out of the timeout was a disaster. Ryan Arcidiacono isolated in the right corner, drove into a well-set defense and had his jumper blocked.
Eventually, the Thunder would rally from what had been a 22-point deficit in the third quarter to take a 109-106 lead when Chris Paul hit two free throws with 1.3 seconds left. The Bulls had no timeouts left, so instead of advancing the ball into the frontcourt and drawing up a play, they could only watch as LaVine helplessly launched a 51-foot 3-pointer that had no chance at the buzzer.
After a 111-104 loss to the Celtics at home, Boylen further explained his timeout philosophy.
"We practice to not have timeouts," Boylen said. "I’m not in fear mode that we don’t have timeouts, because we’re prepared to not have them."
In the final minute of the first half of a loss to the Mavericks, Bulls big man Daniel Gafford rolled his ankle badly and writhed on the floor in pain. After Dallas got a bucket, the officials blew the whistle to stop play. Mavericks coach Rick Carlisle pointed out that because it wasn’t a dead ball situation, the Bulls had to use a timeout if they wanted to substitute for the injured Gafford.
"I’m not going to save a timeout when I got a guy out there that looks like he got really hurt," Boylen said. "That’s not what I’m about."
With the Bulls trailing 127-102 with 1:04 left to play against the Raptors late on a Super Bowl Sunday afternoon, Boylen called a timeout.
And Raptors television analyst Jack Armstrong lost his mind.
"Jim Boylen, what are you doing?" Armstrong said. "Like, seriously. What strategy are you talking? It’s a 25-point blowout, there’s 1:04 left, it’s Super Bowl Sunday. I want to get out of here!
"Look, come on. Really. Do you really need to run a play here?"
Owning 37-79 mark in his Chicago tenure as he spoke, Boylen explained prior to a home game that he doesn’t judge himself by his record and that Bulls ownership and management wasn’t evaluating him on wins and losses as much as player development – despite management and Boylen setting the playoffs as their goal back in training camp.
Boylen’s comments came off poorly to a fan base frustrated by losing. And how did Boylen digest his win-loss record?
"It is hard for me," Boylen said. "But that’s not my calling. That’s not what they ask me to do. Nobody in this organization said to me, ‘You got to win this many games.’ Nobody said to me, ‘Hey, we’re going to talk about wins and losses all year.’ Not one time have they said that to me. That doesn’t mean we don’t want to win. It doesn’t mean we aren’t trying to win, but nobody said that to me."