This could be DeMar DeRozan's last shot at a big payday

The future remains uncertain for Deebo.

© Nick Turchiaro-USA TODAY Sports

The Chicago Bulls and star wingman DeMar DeRozan are at a crossroads. With the 14-year-pro entering the final season of his three-year contract, talk about DeRozan's future with the Bulls has grown louder as his tenure in Chicago has been a mixed bag.

His arrival, coupled with the superb play of then-starting point guard Lonzo Ball, propelled the Bulls to new heights before the latter went down with a career-altering injury. His second season, though, was a disappointment. Despite posting solid All-Star numbers, the Bulls failed to reach the postseason, setting the stage for DeRozan's tricky contract situation.

Unrestricted free agency

Deebo is set to become an unrestricted free agent next summer. This means that if he and the Bulls cannot agree on a new contract, he could walk away from Chicago and leave the team with nothing but memories. This would be a disastrous scenario for the Bulls, who are already struggling to remain relevant in the Eastern Conference.

"DeMar DeRozan is set to become an unrestricted free agent in the summer of 2024. While it's still possible for the Chicago Bulls to come to terms with DeRozan on an extension before that happens, it's not hard to imagine that the two sides head into the regular season without a deal done," Elias Schuster wrote.

To that end, it would be in DeRozan's best interest to have a spectacular season with the Bulls to put himself in a position to earn a favorable deal. The 6-foot-6 midrange master can put up big numbers, but the question remains: Can he elevate the Bulls to the next level?

Worthy of a big payday

To be fair, DeRozan's play at this point of his career could justify a hefty contract. If making two All-Star teams and an All-NBA team in the last three years isn't enough to prove that, his stats make a strong case. The 34-year-old averaged 26.2 points, 4.9 rebounds, and 5 assists per game while shooting 50 percent from the field in his last two seasons.

"To be clear, DeRozan has already proven that he deserves a sizable payday on his next deal. By signing with Chicago and making two All-Star Games and an All-NBA Team, the mid-range master has made 29 other teams look silly for undervaluing him in 2021 free agency," Schuster added. "But this remains a "what have you done for me lately" kind of league. If he enters the year without a new deal, he'll want to ensure that he continues to compete at the same level he has the past two seasons and lock in another big payday."