The Chicago Bulls will be on the clock with the 11th pick in the 2024 NBA Draft on June 26. Days later, they will be faced with major decisions about DeMar DeRozan and Patrick Williams’ free agency and Zach LaVine’s trade market.

Still, the most important matter is what to do with Alex Caruso as he enters the final year of his contract.

Starting July 6, Caruso is eligible to sign a four-year, $78.8 million extension — a big raise off of the $36.9 million contract he will finish out in the 2024-25 season.

Caruso does for the Bulls’ defensive culture and identity what DeRozan does for their offense. Given the team’s stated desire to remain competitive, they have resisted trading Caruso despite tantalizing offers. 

The Bulls took calls on Caruso, but never made them. According to a source with knowledge of the situation, the Bulls have received offers from multiple teams, consisting of multiple protected first-round picks ahead of the 2024 Trade Deadline. One of those deals included a pick that ended up in the top-10 of the 2024 Draft, the source said. The Golden State Warriors were among teams who made a strong offer for Caruso, multiple sources confirmed.

Ultimately, they declined.

Internally, the Bulls party line was that they would have to start searching for a Caruso replacement from the moment they traded him. That may have been fine in a rebuild, which lead executive Arturas Karnisovas admitted ownership supported.

However, the source indicated that there was a mandate from the Reinsdorfs to fight for the Playoffs. That, no doubt, impacted the front office’s decision making when it came to pulling the trigger on any Caruso deal.

Pressure from ownership to compete helps make sense of the Bulls lack of direction, even though it conflicts with what Karnisovas publicly stated. It may also mean the Bulls continue to be reluctant to move Caruso as long as their mandate to remain competitive still applies. It’s unclear whether that is still the case.

Having passed on opportunities to trade him, the Bulls must look more seriously at the trade market or attempt to extend him before he becomes a free agent.

They may have the inside track on keeping him — it’s possible Caruso, given his perpetual risk of injury, prefers to lock in long-term security with an extension. He may instead prefer to test free agency where he will likely attract equal or better offers in team contexts more conducive to winning.

The Bulls have a pattern of outbidding a seemingly barren marketplace to keep their players. But extending him also comes with legitimate risks.

In the new Collective Bargaining Agreement (CBA), veteran extensions start at 140 percent of a player’s salary in the final year of his contract, except in cases where the player makes less than the NBA’s average salary. Since Caruso will be below league average, his extension will start at 140 percent of approximately $12.5 million, the projected average salary, which has yet to be released.

From there, Caruso’s max extension, including eight percent annual raises, is as follows:

• 2025-26: $17.5 million for age 31 season
• 2026-27: $18.9 million for age 32 season
• 2027-28: $20.4 million for age 33 season 
• 2028-29: $22.04 million for age 34 season

That’s a lot of money, but the two-time All-Defensive team guard has outplayed those numbers by a wide margin.

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Excluding rookie scale and max contracts, Spotrac.com’s NBA contract value tool ranks Caruso’s $9.8 million figure from 2023-24 as the 11th best-value contract in the league. In fact, according to Stephen Noh‘s simple salary model, Caruso was worth $28.3 million in 2023-24 alone. 

But the Bulls can’t pay for past production. Committing to Caruso means betting that his elite performance maintains into his mid-30s, and that they can cash in on him down the line. But will he still hold long-term trade value if he cannot replicate the career-highs in both games played and three-point shooting he put up last season? What if he doesn’t make an All-Defensive team for a third straight year? What if he gets hurt?

The best solution is to move Caruso now, even if he cannot generate the same return as he would have at the previous trade deadline. Caruso’s impact on a bargain deal made him a compelling trade target. But the reason he generated such strong offers was because he had two playoff runs left on his current deal. Now, that number is cut in half. Will similar offers be available in the final season of his contract or on an extension? Or have they missed their opportunity to sell Caruso at his highest point?

Still, he holds considerable value. His bird rights alone should be particularly attractive to over-the-cap contenders. Trading him now, as opposed to waiting until the 2025 Trade Deadline, would avoid the risk of any potential injury or declines in performance while securing assets for potential rebuild or retool.

The Bulls have let nearly all of their assets turn into liabilities. They can’t let the same happen with Caruso. Extending him assumes significant financial and performance-related risks. Waiting for free agency could result in losing him for nothing to better offers from legitimately competitive teams.

Trading him, while perhaps not as lucrative as past offers, is the most prudent choice. It allows the Bulls to capitalize on their one remaining valuable asset and better position themselves for the future, rather than exposing themselves to significant downside for a Play-In push they may be able to make without Caruso in a weak Eastern Conference.