Chicago Bulls are back on the clock with DeMar DeRozan as they chase a free-agency deal

The Chicago Bulls are back on the clock with DeMar DeRozan.

Technically, the clock restarted just before 10 p.m. on Monday night as the Boston Celtics claimed their 18th NBA championship with a win over the Dallas Mavericks.

There used to be a slight pause after the playoffs ended and before free agency began. But the NBA’s new collective bargaining agreement lengthened the runway for teams, allowing them to begin negotiations with their own free agents the day after the last game of the NBA Finals. Previously, this wasn’t allowed until June 30, if teams were playing by the books. That meant the Bulls gained more than two weeks of a negotiation period with their top offseason target.

The free-agency moratorium doesn’t officially end until July 6, when teams will be free to ink deals with free agents. But for teams like the Bulls, who are seeking to re-sign free agents like DeRozan, most of the work to get those deals done will be accomplished in the next two-and-a-half weeks.

The Bulls are now in the same position they’ve occupied for nearly a full calendar year: attempting to finalize a deal with DeRozan.

DeRozan has been insistent on his intention to remain in Chicago. But for a brief moment after the Bulls’ play-in tournament loss in Miami for the second year in a row, it seemed like he could have a change of heart.

In a muted postgame press conference, he acknowledged the reality of his age, the weight of making decisions for his family and the desire to chase down an elusive championship. And it was clear that three years of falling short with the Bulls — not just of a ring, but of any level of playoff competition — was beginning to take its toll. But barely a month later, DeRozan was back to emphasizing his love of Chicago and desire to re-sign with the Bulls during an interview on Lou Williams’ Run It Back podcast.

“It’s definitely a place I would love to return to and take care of unfinished business,” DeRozan said on the show.

Messaging from executive vice president of basketball operations Artūras Karnišovas and the Bulls front office has remained similarly consistent. The Bulls love DeRozan. They want him in Chicago. They see him as a key to the next stage of success for the team.

And with all this in mind, they could have re-signed DeRozan at any point during the past year. So why haven’t the two parties reached an agreement? The issue, of course, comes down to price.

DeRozan dodged conversations about the specifics of negotiations during the season, but joked at the trade deadline that he viewed the conversations as a back-and-forth talk akin to a romantic squabble.

Bulls forward DeMar DeRozan complains about a call in the first half on March 18, 2024, at the United Center. (Brian Cassella/Chicago Tribune)

“It’s kind of like with your spouse,” DeRozan said. “It’s like, ‘What do we need to do to work on this, baby? Let’s figure this thing out. You want me. I want you.’ The love is there.”

The Bulls were in a similar situation last summer as they approached free agency with Nikola Vučević — an aging All-Star who was likely most highly valued in Chicago, plus a mutual desire for nothing to change. But Vučević’s negotiation was more open and shut simply due to his salary. His three-year, $60 million deal, while perhaps slightly over market value, did not operate as a hindrance for the Bulls. And coming off a four-year, $100 million deal previously signed in Orlando, Vučević took a slight salary dip that reflected a decline in his production.

DeRozan is on much different footing. After completing a three-year, $81.9 million contract with the Bulls, he is eligible to sign a contract worth up to $129.7 million over three years. That ceiling is unlikely to be reached as the Bulls have shied away from three-year options, but the front office still reportedly floated a two-year deal worth up to $40 million – nearly a 46% increase from his prior contract.

For a team still struggling with the albatross salaries of Lonzo Ball and Zach LaVine, taking a leap on any player is a major risk. The new CBA will give the Bulls a bit more wiggle room on all three salaries, but the front office is still at risk of entering the luxury tax — and that’s previously been a line ownership has only crossed for a guaranteed top-four finish in the East. This would likely mean making sacrifices in other areas, such as giving up on a future with Patrick Williams, who entered his first free agency this summer.

DeRozan’s longevity is undeniable: he’s only the sixth player in NBA history to average at least 24 points and five assists at 34. But a long-term, high-cost investment in a player who will turn 35 in August doesn’t align with the changes the Bulls have articulated following a second year of missing the playoffs.

DeRozan himself has to be clear about the stakes in setting his next deal, as it could be one of the last contracts he signs in the NBA. The Bulls have not been close to playoff-ready for two seasons. Even with a savvy draft pick and LaVine back on the court this season, it’s unlikely this team would rise to meet the level of the world-beater Celtics squad that just took home a trophy. And if the Bulls did shake out a more team-friendly deal, it would be a natural question for DeRozan to wonder “could I get this salary and a ring somewhere else?”

The future might seem inevitable for DeRozan and the Bulls, but there’s plenty of work to be done to transform those words into an inked contract. It’s time to get back to the drawing board — and the negotiations table — for both sides.

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