The NBA world can’t stop buzzing right now. Trades are flying, and even the Los Angeles Lakers made a historic ownership change. The Boston Celtics aren’t far behind in making headlines. They reached the Eastern Conference Semifinals this season before falling to the New York Knicks. But the journey wasn’t smooth. Jalen Brown played through a knee issue, later needing surgery. Kristaps Porzingis struggled with illness late in the postseason. Yet, the biggest heartbreak? Jayson Tatum tore his Achilles without contact in Game 4, ending his season early.

Things got worse. Shams Charania recently reported that Tatum will miss the entire 2025-26 season. That changes everything. Boston already made a move, trading Jrue Holiday to the Blazers. In return, they got Anfernee Simons and two future second-round picks. While this was meant to ease their financial strain, the latest update is raising eyebrows. What seemed like a new start might just be a pit stop.

That’s because, according to Shams on the Pat McAfee Show, “The Celtics are open to rerouting Anfernee Simons elsewhere in a separate trade.” That’s a major twist. Boston might not even hold on to their newest addition. Instead, they could flip him again to gather more draft assets. Simons is on an expiring deal worth nearly $27.7 million. If they trade him, it could help Boston stay under the second tax apron. With Tatum sidelined, Stevens might prefer flexibility over committing to another high-salary player. And despite Simons’ scoring talent, Boston has reasons to stay cautious.

So what does this mean for the Boston Celtics? With Holiday gone, Tatum injured, and Simons possibly leaving, the core is thinning. There’s added uncertainty around veteran Al Horford, too. Shams explained, “I am told he has a pretty robust free agency market outside of Boston potentially this off-season.” Pat McAfee even joked, “Is he going to play till he’s 50? Who knows? We shall see.” Shams replied, “He really looks like he could. He looks the exact same as he did like 15 years ago.” If Horford walks, Boston will lose another locker room leader. In such chaos, can any player feel secure?

There’s still time. Simons is a proven scorer, but he’s also not a strong defender. Whether he stays or not, this offseason will define Boston’s next chapter.

If the Celtics keep Anfernee Simons, here’s how it could work out

If Boston decides to keep Anfernee Simons, it could be more than just a salary dump deal. Simons brings legitimate offensive firepower, especially with Jayson Tatum expected to miss most, if not all, of the upcoming season. Over the last three years with Portland, Simons averaged 20.7 points and 4.7 assists while hitting 37.4 percent from beyond the arc. In 2023-24, he posted a career-best 22.6 points per game and drilled 38.5 percent of his threes. That’s the kind of shot creation Boston will desperately need.

He also fits seamlessly into Joe Mazzulla’s three-point-heavy system. As noted by WEEI’s Justin Turpin, “From the start of the new year through the end of the season, Anfernee Simons averaged 3.4 made threes per game, the fifth most in the league during that span (min. 30 GP).” Only Steph Curry, Anthony Edwards, Malik Beasley, and Derrick White were ahead of him. That type of volume shooting will open up spacing for Jaylen Brown, Derrick White, and others to drive or kick.

However, there are concerns defensively. Simons is 6-foot-3 and lacks the physical presence of Jrue Holiday. With Payton Pritchard also on the roster, that creates a size mismatch in some lineups. But Boston might try to hide him on the weaker offensive player or shift more defensive responsibility to White and Brown. Simons’ shot-making upside may still outweigh his defensive flaws, especially in a scoring-starved season.

Financially, his expiring $27.7 million contract adds more strategy into the mix. The Celtics could keep him and see how he performs, or let him walk to clear cap space. Either way, he gives Boston options. As Conor Ryan wrote, “Simons’ expiring contract could also make him a potential trade chip for Boston this year, especially if Boston is heading toward a bridge year with Tatum on the sidelines.”

And don’t forget, this isn’t a player fresh off college or G League stints. Simons made a straight leap from prep basketball at IMG Academy to the NBA, taking advantage of a unique draft loophole. His path has always been unconventional, and Boston’s use of him might be the same. Whether he stays or goes, Simons is already shaping up to be a key piece of Boston’s most unpredictable offseason in years.