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Would Billy Donovan leave the Chicago Bulls to join Kentucky basketball?

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On the night of the NBA trade deadline, the Chicago Bulls were in Memphis, Tennessee.

Arturas Karnišovas, the franchise's head basketball manager, held an afternoon video conference with reporters to answer why he did nothing to improve the Bulls' roster at the deadline for the third straight season.

Hours later, in a cramped interview room before the game against the Grizzlies, Bulls coach Billy Donovan was offered the opportunity to offer his perspective on the state of the franchise.

He was asked whether the team would stand by his side again and stubbornly stick to continuity. He was asked about the team's stunningly mixed results – how the Bulls have admirably chosen to chase nightly competitiveness but remain undeniably mediocre. Donovan was even asked about responsibility and whether the team's performance could impact his job.

If Donovan ever had a chance to voice his displeasure with the Bulls' direction, that second Thursday in February would have been the time. The Bulls, battered and battered at the time by season-ending injuries to Zach LaVine and Patrick Williams, were unable to secure enough replacements nor did they attempt to sell assets to prepare for the future. And here was Donovan, at the start of a four-game road trip leading into the All-Star break, tasked with making the most of this season.

Donovan, a respected coach who won two college championships at the University of Florida, could have expressed confusion and despair that every effort is not being made to give the Bulls the best chance to win. Because of his way with words, Donovan could have done it without directly criticizing his boss. But he never became even remotely critical. Instead, Donovan played the role of company boss.

“The group has gotten better,” Donovan said Feb. 8. “Is it at the level we want? Absolutely not. Do we want to have a loss balance? No. But I think the team performed and played better after that start (5-14).”

It had nothing to do with the fiery, no-nonsense coaching college fan Donovan remembers from his time at Florida. The youthfully exuberant coach chasing the next win, the next championship, the next thrill is long gone.

But a true measure of Donovan's feelings toward the Bulls could come in the next few weeks as Kentucky basketball has a chance.

Donovan has been listed as a candidate to replace John Calipari as the longtime Kentucky coach signs a move to Arkansas. Given his college resume, Donovan's name is a natural connection when major college positions open up. He coached at Kentucky for five seasons from 1989 to 1994 under his mentor Rick Pitino. Donovan won back-to-back national titles with the Gators in 2006 and 2007. He owns a .709 winning percentage in 708 career games as a coach at Marshall and Florida.

Donovan coached the Oklahoma City Thunder for five seasons before joining the Bulls. He won 60.8 percent of his 400 regular-season games and reached the 2016 Western Conference finals. The Thunder made the playoffs in each of Donovan's five seasons, but fell in the first round after the 2015-16 success.

On the other hand, the Bulls only had one winning season during Donovan's tenure. They only won one playoff game. The team's regular season record under Donovan is 154-160.

But it would be wrong to place the blame solely on Donovan. Over the past two seasons, Donovan has coached ill-fitting and injury-prone squads that finished near .500. He formed the league's fifth-ranked defense last season despite great adversity due to obvious personnel deficiencies. He also had a hand in the development of Coby White and Ayo Dosunmu, although Donovan is quick to praise both players and cites their work ethic.

One could argue that Donovan did what he was brought to Chicago to do, bring the Bulls back to prominence. Remember, the Bulls went 112-199 in the four seasons before Donovan. Also keep in mind that few expected Donovan to leave the Thunder for the Bulls.

When the Bulls played in Oklahoma City the night before Thanksgiving this season, Donovan explained his decision to leave the Thunder. His answer then offers some possible insight into his thought process with Kentucky's opening.

“For me it was more about who am I working with? The vision,” Donovan said on November 22nd. “Who am I connected to? Who do I share something with every day? Such things. Those were my decisions. It wasn't necessarily always about the team, because that can always change. Something can always happen. But for me it was more just sitting with Artūras (Karnišovas) and Marc (Eversley) and having the opportunity to meet them and hear from them.”

Donovan remained in Florida for 19 years, due in large part to his close relationship with Jeremy Foley, now athletic director emeritus.

After four seasons in Chicago, the question may not be whether Donovan has taken the Bulls as far as he can go, but rather whether the Bulls have done everything they plan to do to maximize Donovan?

After the Bulls lost to Milwaukee in five games in the 2022 playoffs, it was clear that changes were needed. Nevertheless, the front office led by Karnišovas fielded virtually the same roster twice more. The results are no surprise to anyone, as the Bulls fought to get into the playoffs via the play-in tournament last season and again this season. Chicago won its first play-in game last season but lost its second and missed the playoffs.

“It’s the same thing I dealt with in college,” Donovan said Feb. 8. “You want to advance in the NCAA tournament. They want to advance in the playoffs. And our group made the playoffs the year before last, and there was a play-in last year. And we want to move forward. We didn’t do that.”

Despite the Bulls' shortcomings, by all indications Donovan's job is safe. He signed a multi-year contract extension before last season and has close working relationships with Karnišovas and Eversley.

But the Bulls won't engage in a bidding war for Donovan, and Kentucky could easily up the ante. Donovan reportedly earned $24 million during his first four-year contract. Calipari was reportedly scheduled to make $8.1 million next season and $8.6 million in each subsequent season through 2029.

However, more money from the Wildcats would mean significantly higher expectations for Donovan. The pressure to win in Lexington exceeds the pressure in Chicago. Little about Donovan today suggests he's ready to step into that fire. Try trumpeting a 14-9 stretch at Kentucky. Anything other than the title is a disappointment. BetMGM released its 2025 Men's College Basketball Championship odds on Monday. Kentucky and North Carolina have the fifth best odds at +1800.

Donovan abandoned his win-at-all-costs mentality in Florida in the mid-2000s. Plus, a lot has changed since Donovan left college.

Recruiting and rigged rules had already exhausted Donovan by the time he jumped to the Thunder in 2015. Three years later, the NCAA launched the transfer portal, giving student-athletes the opportunity to transfer between member institutions. And over the past five years, college athletics has seen sweeping changes that allow student-athletes to profit from their name, image and likeness (NIL). One agent compared the new landscape to the “wild, wild West.”

Donovan had to adapt. Essentially, the options don’t quite match the trainer. But the choice, when he has to make it, is clear.

Donovan would have to choose between the challenges of the college game, including the pressure of winning or failing to win a championship at a heavily scrutinized program like Kentucky, and remaining in his current comfort zone: the competitive but content Bulls.

(Photo by Billy Donovan: Jonathan Daniel / Getty Images)