Portland Trail Blazers fans had mixed emotions after Anfernee Simons was traded to the Boston Celtics this past summer. On one hand, the Blazers were moving on from one of their best players and, at the time, the longest-tenured player. On the other hand, Simons made it clear that losing was taking a toll on him, and he landed with one of the best organizations.
At the end of the season exit interview following Portland's 21-win season in 2023-24, Simons mentioned he "wanted the opportunity to win." He finally got that with the Celtics, at least for half a season.
Simons was a trade candidate the moment he landed in Boston, as the motivation behind swapping him for Jrue Holiday was primarily financial. Regardless of the trade talks, Simons was excited about his landing spot: "I was excited because I could finally be in the playoffs," he said. "I've been watching for three years and wanted to be part of it."
Anfernee Simons no longer has the "opportunity to win" after joining the Chicago Bulls
Unfortunately, Simons was a trade deadline casualty. He won over Celtics fans, embracing a sixth-man role off the bench and providing the same microwave scoring he had in Portland. But that ultimately wasn't enough to stay. Boston needed to balance out their roster, addressing their frontcourt issues by acquiring Chicago Bulls center Nikola Vučević.
Now, Simons finds himself in a worse position than he was in with Portland.
The Bulls had one of the strangest deadlines of any team, making a total of seven deals and parting ways with eight players, stockpiling "unwanted" guards like Simons, who had low trade value around the league. They brought in Simons, Collin Sexton, Jaden Ivey, and Rob Dillingham, all while having their starting point guard position already solidified with Josh Giddey.
Simons' combo guard skillset should come in handy as it will give him an opportunity to play more minutes at the two alongside Giddey. But the crowded backcourt isn't as problematic as the state of the Bulls franchise in general.
This is a perennial play-in team even in a weak Eastern Conference, which is the definition of NBA purgatory. Chicago sits 11th in the Eastern Conference. That's similar to Portland out west, but the future outlook doesn't look as promising when comparing the two young cores.
This can't be an ideal landing spot for Simons, given his publicly stated desire to win. The silver lining is that his $27.7 million salary is set to expire after this season, meaning he'll have control over his own future to join that winning situation he's always wanted. Still, it's a disappointing development as the Celtics appeared to be an ideal situation in terms of finally being able to play on a contender.