Anfernee Simons landed with the Chicago Bulls as a result of the Nikola Vucevic trade with the Boston Celtics. Unfortunately, that means the former Portland Trail Blazers guard won't have that "opportunity to win" he's always wanted.
After losing took a toll on him with the Blazers, the Celtics seemed like an ideal landing spot for Simons to achieve his goals of finally playing for a contender. The Bulls? Not so much.
Simons finds himself in NBA purgatory with a team that acquired an unreasonable amount of guards at the deadline, and even worse, has no realistic pathway to contention in the coming seasons.
The silver lining for Simons is that his contract is set to expire after this season, giving him the chance to decide his own fate and join that desired winning situation. But could Portland actually fit that criteria now?
Anfernee Simons-Blazers reunion this offseason is suddenly a realistic possibility
Damian Lillard came back to Portland in part because of a basketball decision to join a Blazers team that improved in his absence. The same thing could apply to Simons, as Portland's roster has taken tremendous strides this season.
Although they are in a very similar position in the Western Conference compared to last season, there's much more reason for optimism. Two aging stars have now entered the picture in Lillard and Jrue Holiday. Additionally, their young core has taken a collective leap, headlined by Deni Avdija's first All-Star selection.
Simons has made it clear he wants to win, and, ironically, he can achieve that with a reunion with his former team, which he wanted to leave specifically because he wasn't winning enough. He never formally requested a trade, but it always seemed he was open to the idea. His mindset could have changed after seeing that the grass isn't always greener, particularly after landing in Chicago.
A Simons-Blazers reunion makes sense for both parties. Simons gets to join that winning situation, while Portland adds an offensive-minded combo guard to provide much-needed shooting and playmaking, two of their most significant roster weaknesses.
In fact, Bleacher Report's Grant Hughes recently listed every team's top free agent target following the trade deadline, and for Portland, that was Simons.
"You could argue that they need him more now than they did at any point during that career-opening stretch... If he's willing to accept a bench role going forward, and if Portland's mid-level exception of $15.1 million is enough to entice him, this full-circle re-acquisition could benefit everyone," Hughes writes.
The Blazers fixed some of their floor-spacing issues with the underrated Vit Krejci acquisition at the deadline. But given how bad they are in the three-point shooting department, this is a problem they'll need to continue to address this offseason.
Part of the reason they traded Simons to Boston was their concern about the looming new contract. However, the market doesn't value Simons' player archetype as an undersized offensive-minded guard. So it's possible Portland could land him with a mid-level exception.
Whether he'd welcome a reunion remains to be seen, and there's likely a better situation in which he could win in the short term. But it's at least worth exploring for Portland. The fact that Simons recently got sent to NBA purgatory in Chicago suggests he could be on the move yet again this offseason.