Bulls conundrum: Is DeMar DeRozan worth an extension?

In two years with Chicago, DeRozan has averaged 26.2 points, 4.9 rebounds and five assists per game. Perhaps his greatest impact, though, is leadership. He has embraced the young, still-developing talent the front office believes is the key to the team's future. 

DeRozan has routinely made himself available for skills training for other players during the offseason, and after two offseason workouts with DeRozan, Patrick Williams — DeRozan's prized pupil — is expected to have a potential breakout season in 2023-24.

An argument can be made that DeRozan has outperformed his contract as well, which is roughly 20% of the team's cap, given his contributions on and off the court. His individual success, though, creates a condundrum for the organization. 

Despite DeRozan's best efforts, poor roster construction and mismanaged roles within the offense have led to suboptimal results. Chicago has only one playoff win the past two seasons. 

In July, DeRozan became eligible for a well-deserved pay raise, as reported by Daniel Greenberg of Chicago Sports Updates. 

If he were 27, a raise would be no issue, but DeRozan turned 34 on Aug. 7 and has reached the point in his career where organizations should question how much should be invested in a player for past performances. 

A contract extension, with a possible annual salary of $40 million-plus, for a player who will soon be leaving his prime is not a foregone conclusion. The Bulls don't want to be caught in a bidding war against themselves.

Doubling down on continuity with DeRozan likely will come at a major price. Can the Bulls afford to ante up?