October is here, and so is the NBA. Training camp kicks off, preseason is near, and the regular season isn’t far behind. For the Chicago Bulls, it all begins on October 22, when they face the upstart Detroit Pistons to open the campaign.

But not so fast. Just two days before the regular season opener, the Bulls’ front office has a major contract decision looming—whether to extend former first-round pick Dalen Terry as he enters his fourth year with the franchise.

Dalen Terry’s extension timeline sparks uncertainty

October 20 is the final day to extend Terry. If Chicago passes, the 6-foot-7 wing will be on track for restricted free agency in the 2026 offseason, but only if the Bulls first decide to tender him a $7.6 million qualifying offer next summer.

Yet, every path to keeping Terry comes with complications. The former first-rounder hasn’t exactly impressed through three seasons in Chicago, but his size, athleticism, and two-way potential still make him an intriguing piece.

Through 170 games, Terry owns career averages of 3.5 points, 1.6 rebounds, 1.2 assists, and 0.5 steals per game. He’s shot 44.5 percent from the field and just 29.8 percent from deep, with little sign of progress in either area. Even in his best season last year, the numbers only nudged to 4.5 points, 1.7 rebounds, 1.3 assists, and 0.6 steals per contest.

Still, he passes the eye test. Terry might not shoot confidently, but he plays hard, handles the ball well, attacks the rim, and makes an impact defensively. His defensive counting stats don’t tell the full story, but the Bulls were better defensively with him on the floor, and he ranked fourth among Bulls who appeared in at least 41 games in defensive rating. And, at only 23 years old, he fits Chicago’s timeline.

The question marks make it hard to hand Terry a sizable extension, something the Bulls’ brass has certainly discussed throughout the summer. A modest deal, similar to what Ayo Dosunmu received in 2023, could be an option, but it’s also up to Terry, who may feel he has more to show than he has over the past three seasons.

Terry will likely spurn any extension, if one is even offered, opting for another season to prove his worth. The former Wildcat has reportedly been turning heads and could even be in the mix to start at small forward. If he exceeds expectations in 2025-26, he could earn a long-term contract with the Bulls next offseason.

If Terry continues to underwhelm, it’ll be back to the drawing board. He’ll likely accept the qualifying offer, if one is extended, or take a bargain “prove-it” deal to show he belongs in an NBA rotation. For now, Chicago must decide whether he’s worth the gamble—and they have less than three weeks to make that call.