Anfernee Simons’ NBA journey has taken another unexpected turn - and this one’s a bit tougher to spin as a win.
After a summer trade that sent him from Portland to Boston, Simons finally got what he’d been asking for: a shot at meaningful basketball. The Trail Blazers, coming off a 21-win season, were clearly rebuilding, and Simons made no secret of the toll that losing had taken on him.
“I wanted the opportunity to win,” he said during his exit interview in Portland. Boston gave him that - at least for a few months.
Landing with the Celtics was a breath of fresh air. Simons embraced a sixth-man role, coming off the bench and doing what he does best: score in bunches.
That microwave scoring punch, which had long been his calling card in Portland, translated well to a contender. He gave Boston fans a glimpse of what he could bring to a playoff-caliber team.
And for the first time in his career, he was in the thick of a postseason push instead of watching it from home.
But just as quickly as it came together, it unraveled.
At the trade deadline, Simons was dealt again - this time to the Chicago Bulls - as Boston pivoted to address its frontcourt depth by acquiring center Nikola Vučević. It was a move that made sense for the Celtics financially and roster-wise, but it sent Simons from a title contender to a franchise stuck in neutral.
Chicago’s deadline was one of the busiest - and most puzzling - in the league. The Bulls made seven trades, moved eight players, and brought in a collection of guards that reads more like a fantasy draft than a cohesive roster plan. Alongside Simons, the Bulls added Collin Sexton, Jaden Ivey, and rookie Rob Dillingham, despite already having Josh Giddey entrenched as their starting point guard.
For Simons, the fit is... complicated. On the surface, his combo guard game should allow him to slot in next to Giddey at the two, where he can continue to score without the burden of full-time playmaking. But the bigger issue isn’t the backcourt logjam - it’s the state of the Bulls as a franchise.
Chicago is sitting 11th in the Eastern Conference, hovering just outside the play-in picture. They’re not bad enough to tank, not good enough to contend - the classic NBA purgatory.
And while Portland may not be winning now either, their young core offers a clearer path forward. The Bulls?
Not so much.
This isn’t the kind of situation Simons had in mind when he talked about wanting to be part of a winning culture. After finally getting a taste of playoff basketball, he’s now back in a spot that looks eerily similar to where he started - only this time, the future feels even murkier.
There is, however, one silver lining: Simons’ $27.7 million salary comes off the books at the end of the season. That means he’ll have the freedom to choose his next stop - ideally, one that aligns with his desire to compete at the highest level. Until then, he’ll have to navigate the rest of this season in Chicago, a team still trying to figure out what exactly it wants to be.
It’s a tough break for a player who’d finally found a rhythm on a contender. Simons showed he could contribute to a winning team. Now the challenge is doing it again - this time, in a far less stable environment.