Blockbuster $97 Million Trade Proposal Links Celtics to Anfernee Simons Deal as Boston Eyes Repeat Title with Bold Reinforcement

The Boston Celtics, fresh off their record-breaking 18th NBA championship, are not resting on their laurels. In a move that could send shockwaves across the league, reports indicate that the Celtics are seriously considering a blockbuster trade proposal worth $97 million, potentially bringing high-scoring guard Anfernee Simons to Boston. The deal would mark yet another bold front-office maneuver in what has already been a masterclass of team-building by Celtics President of Basketball Operations Brad Stevens.

Anfernee Simons, the Portland Trail Blazers guard known for his electrifying scoring ability and rapid development, has become a coveted asset as the Blazers shift into a youth-focused rebuild around Scoot Henderson and Shaedon Sharpe. Simons, 25, averaged 22.6 points and 5.5 assists per game last season, all while shooting over 38% from three. He possesses the kind of microwave scoring talent that could elevate Boston’s already elite offense into an even more lethal force.

Sources close to the discussions suggest that Boston’s interest in Simons is centered on boosting offensive versatility behind Jayson Tatum and Jaylen Brown, while preparing for a potential roster evolution should Derrick White or Jrue Holiday become future trade chips or cap casualties. While Celtics fans might be hesitant to see a beloved role player or pick package sent out, this potential acquisition would be a calculated risk—one rooted in maintaining Boston’s championship window for years to come.

It’s clear the Celtics are not simply satisfied with their 2024 championship triumph, which featured a dominant postseason run culminating in a gentleman’s sweep of the Dallas Mavericks in the NBA Finals. Their front office has adopted a philosophy mirrored more by dynasties than one-hit wonders: You don’t defend your title standing still.

Bringing in Simons would almost certainly require significant outgoing salary, and speculation has already begun swirling around Malcolm Brogdon, Payton Pritchard, and even Al Horford as potential pieces to make the trade financially viable. Including draft capital—Boston has limited first-round flexibility but owns enough second-round picks to sweeten offers—would likely be necessary as well.

Critics might question whether adding another score-first guard is a redundancy for a team already stacked with offensive talent. But the Celtics, under head coach Joe Mazzulla, have demonstrated a growing willingness to embrace offensive firepower. Mazzulla’s spacing-heavy, three-point-leaning offensive schemes thrived in 2024 behind elite ball movement and isolation scoring. Simons, a gifted off-the-dribble shot creator, fits that mold. He’s just as comfortable running pick-and-rolls as he is spotting up from 30 feet. His ability to play both on and off the ball would offer tremendous flexibility in Mazzulla’s rotation.

Notably, Simons’ contract—four years, $97 million, signed in 2022—would not expire until the end of the 2026-27 season. That security appeals to a Celtics front office that saw Marcus Smart depart unexpectedly last offseason. Adding a long-term piece like Simons could provide both continuity and cap certainty, especially as the new CBA’s financial restrictions begin to squeeze super teams.

From the Blazers’ perspective, this deal could be the right move at the right time. Portland is clearly in the midst of a rebuild, and despite Simons’ productivity, his presence might be logjamming the development of Scoot Henderson, the No. 3 overall pick in the 2023 NBA Draft. By offloading Simons’ salary, Portland could take on expiring deals, add draft picks, and create more on-court opportunities for Henderson and Sharpe. A veteran like Horford could help stabilize their young locker room if included, while Pritchard’s Oregon roots make him a fan-favorite possibility.

In many ways, this rumored trade mirrors the Celtics’ recent pattern of bold moves. In the last 14 months alone, Boston has acquired Kristaps Porzingis and Jrue Holiday, shipped out long-tenured heart-and-soul players like Marcus Smart and Robert Williams III, and reshuffled its roster without compromising championship viability. Each transaction has paid off, culminating in an NBA-best 64-18 regular season record and a dominant postseason campaign.

Bringing in Simons would undoubtedly shift the team’s identity further toward offense. But it’s not without strategic sense. Holiday and White are both defensive stalwarts but neither is a prolific scorer. Tatum and Brown remain the foundational wings, but additional shot creation has occasionally bogged Boston down in half-court sets, especially when Tatum sits or defenses collapse around Brown. Simons could provide instant buckets, serve as a high-usage sixth man, or even close games depending on matchups.

What might complicate the deal, however, are the salary cap implications. With the NBA’s new luxury tax penalties and second-apron restrictions tightening flexibility, the Celtics would need to tread carefully. Trading for Simons could push Boston further into punitive territory, especially with the extensions for Holiday and White already on the books. The front office will need to weigh short-term talent gain against long-term financial health—though team owner Wyc Grousbeck has made it clear that he’s willing to spend as long as titles are in reach.

Still, it’s difficult to ignore the precedent that has been set. Boston has shown that it is not afraid to part with fan favorites, key role players, or even future assets if it means upgrading the present. In an Eastern Conference that still features rising powers in Milwaukee, New York, and Philadelphia, staying aggressive might be the only way to stay ahead.

There’s also the Jayson Tatum factor. With his extension looming and his voice growing louder in organizational decisions, keeping him happy and competitive is paramount. Tatum has consistently emphasized winning as his top priority and would likely welcome reinforcements—especially one like Simons, who could relieve scoring pressure during the long regular season and high-stakes playoff games alike.

The message being sent by Boston is loud and clear: Winning one title is never enough. The Celtics are chasing dynasty status, and this rumored trade for Anfernee Simons could be the next chess move in a grand plan to make Boston a powerhouse for the next five years.

While nothing is official yet, multiple league insiders suggest the talks are progressing steadily, and there’s mutual interest on both sides. The NBA offseason is far from over, and as we’ve seen time and time again, the Celtics are rarely idle when opportunity knocks. If this deal comes to fruition, it could be the latest masterstroke by Brad Stevens—and another reason the rest of the league should be very, very nervous.

As fans await final word, one thing is undeniable: Boston is not done building. If Simons walks through those TD Garden doors this fall, the road to another championship might run squarely through Beantown once again.