The Boston Celtics were primed to be one of the most threatening teams in the league last season. As the defending champions, this status was justified. Unfortunately, as injuries and shortfalls derailed their campaign, the Celtics were faced with a significantly harsher reality in the offseason.
The second luxury tax apron hit the Celtics hard, and to avoid paying a massive tax bill, the front office had to make some tough decisions.
After trading Jrue Holiday, the Celtics acquired a talented young guard in Anfernee Simons from the Portland Trail Blazers.
Unfortunately, with the Celtics still marginally above the second apron, the front office has reportedly been engaging in trade discussions around their newly acquired guard.
Last season, Simons recorded an average of 19.3 points, 2.7 rebounds, and 4.8 assists a game while shooting 42.6% from the field and 36.3% from beyond the arc. There is no doubt that such numbers would be of interest to teams looking to add a second scoring option to their backcourt.
With this in mind, we explore six likely trade destinations for the 26-year-old.
Milwaukee Bucks
The Milwaukee Bucks decided to part ways with their star point guard, Damian Lillard, by waiving him this offseason. With the need for a reliable point guard, the Bucks could look to engage in a trade with the Boston Celtics to acquire Anfernee Simons.
Proposed Trade Details
Milwaukee Bucks Receive: Anfernee Simons
Boston Celtics Receive: Kyle Kuzma, AJ Green, 2027 first-round pick (NOLA)
For the Celtics, the addition of Kyle Kuzma and AJ Green has very little value in terms of what they can contribute to the team. But on short-term deals, Boston could look to offload them in the following season.
Meanwhile, the Bucks would receive the ideal replacement for Lillard. Considering that Simons was viewed as Lillard's replacement in Portland as well, Milwaukee would effectively be acquiring the same type of player.
Although Simons isn't a great playmaker, his ability to score is not to be overlooked. His athleticism and long-range shooting ability make him an offensive threat at multiple levels.
The Bucks could benefit from this, especially with Myles Turner's acquisition headlining their offseason roster construction. With two capable defensive players in the frontcourt, Simons would have ample opportunity to facilitate the scoring opportunities for this Bucks side.
Chicago Bulls
The Chicago Bulls have recently been exploring trade possibilities for Ayo Dosunmu and Coby White. While considering their imminent need for a young guard, Simons could be an ideal target for Chicago.
Proposed Trade Details
Chicago Bulls Receive: Anfernee Simons
Boston Celtics Receive: Ayo Dosunmu, Kevin Huerter, 2028 second-round pick
The trade has value for both teams. As the Celtics continue to shed salary with their offseason moves, the acquisitions of Ayo Dosunmu and Kevin Huerter, both of whom are on expiring contracts, aid this process. The 2028 second-round pick only serves to sweeten the deal.
Meanwhile, the addition of Simons could be beneficial for the Bulls in multiple ways. Considering that the 26-year-old is also on an expiring contract, Chicago could simply ride out the season with him and shed salary to clear cap space next summer. But there would be merit in retaining the guard as well.
The Bulls are currently seeing the growth of a star in Matas Buzelis. By pairing him with another young and capable prospect, Chicago could be setting up the future of their franchise.
The opportunity is certainly exciting considering the offensive capabilities of the two young players. When factoring in the presence of reliable veterans on the roster as well, the Bulls could proceed with constructing their roster around their new core.
Utah Jazz
The Utah Jazz continue to be a team in rebuild. While there are no significant moves the team has made, apart from trading John Collins to the Clippers, the team has a dire need for a point guard next season. In this regard, Simons could be the right fit.
Proposed Trade Details
Utah Jazz Receive: Anfernee Simons
Boston Celtics Receive: Jusuf Nurkic, 2027 first-round pick (LAL), 2029 second-round pick
This trade doesn't necessarily make either team better, but it has merit all the same.
The Celtics acquire the necessary big man depth with Jusuf Nurkic. The real benefit lies in the fact that he is on an expiring contract, which allows Boston to clear cap space next season. The addition of the second-round pick only serves to increase their depleted draft capital.
For the Jazz, the addition of Simons serves the need for a point guard. With Collin Sexton headed to the Charlotte Hornets, Utah is lacking on the playmaking front.
Simons may be a limited playmaker, but a backcourt pairing of him and Keyonte George would be explosive. The young duo could make for an exciting offensive pair, and when considering the Jazz's rookie sensation Ace Bailey, Utah could witness the start of an exciting new project.
The challenge here lies with regard to what Utah's plans are for the coming season. After ending last season at the bottom of the Western Conference, there is uncertainty about how competitive the Jazz will be this year.
Should the team opt to tank again, Simons could find himself in a losing situation. In this scenario, unrestricted free agency next summer would allow the 26-year-old to find greener pastures elsewhere.
Miami Heat
The Miami Heat are looking to make some interesting changes to their roster in the offseason. While the point guard position remains vacant, the Heat could look to fill this spot by trading for Simons.
Proposed Trade Details
Miami Heat Receive: Anfernee Simons
Boston Celtics Receive: Terry Rozier, 2027 second-round pick (swap)
This deal, realistically, benefits the Heat more than it does the Celtics. While the Celtics acquire a fairly hefty expiring contract in the form of Terry Rozier, the Heat potentially land their star point guard for the future.
Miami has been looking to change its roster in the offseason. After a disappointing end to their postseason campaign, the Heat made it abundantly clear that they would not be running it back.
To facilitate this, the Heat has already made a huge move to acquire Norman Powell from the Clippers. In addition to this, the acquisition of Simons would be massive for the team's overall strength.
The backcourt pairing of Simons, Powell, and Herro could wreak havoc on opposing defenses. Although it leaves the team marginally undersized, the presence of Kel'el Ware and Bam Adebayo makes for a reliable frontcourt.
Sacramento Kings
The Sacramento Kings have made some efforts to improve their guard rotation with the signing of Dennis Schroder in free agency. But with an opportunity to add a solid young scorer, the Kings may benefit from trading for Anfernee Simons.
Proposed Trade Details
Sacramento Kings Receive: Anfernee Simons
Boston Celtics Receive: DeMar DeRozan, 2026 second-round pick (CHA)
For the Celtics, the acquisition of DeMar DeRozan could be worthwhile. Since he is on a short-term contract, the offensive upside he brings to the team could be worth exploring.
Meanwhile, this trade has much more merit to the Kings, who are actively looking to part ways with DeRozan.
A potential backcourt pairing of Simons and Zach LaVine has a lot of upside, especially when supported by a capable playmaking big man such as Domantas Sabonis.
Simons' offensive arsenal allows him to shoot consistently from distance, which wasn't a preference for DeRozan. This would allow the Kings to enhance their perimeter shooting and diversify their offense.
This move could be considered a short-term arrangement. But the Kings should have enough cap space to offer Simons a new contract next summer if they intend to build a new core unit.
Memphis Grizzlies
The Memphis Grizzlies have already made some significant changes to their roster this offseason. But considering that they intend to part ways with their newly acquired guard Cole Anthony, the Celtics guard could be a suitable target for replacement.
Proposed Trade Details
Memphis Grizzlies Receive: Anfernee Simons
Boston Celtics Receive: Cole Anthony, John Konchar, 2028 first-round pick, 2029 first-round pick (ORL), 2030 first-round pick (ORL)
This trade proposal presents the most intriguing possibilities for both teams. For the Celtics, the first-round picks have more value than the players themselves. However, Cole Anthony and John Konchar are serviceable rotation players at their disposal on relatively friendly contracts.
For the Grizzlies, the acquisition of Anfernee Simons presents an exciting opportunity to form a new core alongside Ja Morant and Jaren Jackson Jr.
A backcourt pairing of Morant and Simons boasts a lot of firepower. With both players possessing tremendous athleticism, the notion of electrifying displays on offense is something Grizzlies fans will look forward to.
Although the imminent challenge of Simons becoming an unrestricted free agent next summer could put a damper on Memphis' plans, the 26-year-old guard would make a solid case for being Morant's ideal running mate.
What's Next For Anfernee Simons?
The current Celtics roster pales in comparison to the one they had last season. Although Simons is a capable player in his own right, Boston's current issues with the salary cap will make it a challenge for him to play there.
It seems quite likely that Boston will facilitate a trade to ensure they get under the second apron. But the challenges of ensuring such a trade goes through could see Simons on the roster for a decent part of the offseason before any move materializes.
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