The Orlando Magic and Boston Celtics have undergone massive roster changes built on foundational philosophical changes in their organization. The Magic knew they needed shooting, so they went out and traded for Desmond Bane and drafted Jase Richardson, both of whom are elite 3-point shooters. The Celtics, meanwhile, have been getting their finances in check by trading a number of their veterans. They dealt Jrue Holiday and Kristaps Porzingis, and they are unlikely to bring back Al Horford. The Holiday trade, in particular, resulted in the team landing Anfernee Simons.
Most fans thought Boston won the Holiday-Simons trade. After all, Simons is the younger, cheaper, and better offensive player, while Holiday is clearly regressing and on a bad contract. Even so, the Celtics are reportedly looking to flip Simons once again. So, could the Magic trade for Simons to bring in even more shooting?
Magic trade proposal for Anfernee Simons
Magic receive: Anfernee Simons
Celtics receive: Jonathan Isaac, Goga Bitadze, Tristan Da Silva
The Eastern Conference is wide open this year. The Celtics have been making contract-motivated moves to get under the second apron because their best player, Jayson Tatum, will miss next season with a torn Achilles. He isn't the only superstar who suffered that fate. Tyrese Haliburton and Damian Lillard also tore their Achilles tendons, the latter of whom has since been released by the Milwaukee Bucks.
The Magic are now in a prime position to make it to the NBA Finals. Paolo Banchero and Franz Wagner form one of the best young duos in the NBA, and the team is filled with defensive specialists. They finished last in the league in shooting from beyond the arc last season, though.
Orlando made one of the biggest offseason moves to fix that problem by trading for Bane. It cost the team four first-round picks, a first-round pick swap, Kentavious Caldwell-Pope, and Cole Anthony. That was quite the price to pay for a non-All-Star, but Bane is exactly the type of player the Magic need. He is a versatile player who can thrive in any lineup, but most importantly, he is one of the best 3-point shooters in the NBA.
Simons would add even more shooting and offense to Orlando's rotation. The guard averaged 19.3 points per game last season, and he was above 20 points per game in each of the two years prior. The IMG Academy alumni gets up greater than eight 3-point attempts per game on average at an efficient clip, too.
With Banchero, Wagner, Bane, Jalen Suggs, and Wendell Carter Jr. entrenched in the starting lineup, Simons could operate as arguably the best sixth man in the NBA. If the team pulled off this trade, even after the Bane deal, they would still have plenty of depth and defense on their roster, and they'd have to be looked at as title contenders.
Would the Celtics flip Anfernee Simons?

The Celtics' trade for Simons made a lot of sense. He is making just over $27 million in what is the last year of his contract. Holiday, meanwhile, is making over $30 million in each of the next three seasons. Simons could also provide an offensive boost in a year where the team's top scorer will be sidelined.
Even so, Simons doesn't appear to be a long-term option for the Celtics, so he could be dealt again. Boston could still get its finances a little bit more in check, and this deal would save them over half a million against the cap, which would help ensure getting below the second tax apron. Additionally, the Celtics don't want to lose Simons for nothing next offseason, and they might not be able to afford to pay him.
Boston's once great depth took a major hit this offseason, too, but this deal lands them three rotation-caliber players. Jonathan Isaac has struggled with injuries and doesn't play starter minutes, but pound-for-pound, he is one of the best defensive players in the NBA. He can lock down guards on the perimeter or play inside and swat shots at the rim.
The team also desperately needs frontcourt depth with the departures of Porzingis and, eventually, Horford. Goga Bitadze is a part of a center rotation that includes Carter and Mo Wagner, so the Magic would likely be okay parting with him. Bitadze is far from a star, but he can provide reliable minutes scoring inside and collecting rebounds.
Tristan Da Silva would also be a good get for the Celtics. The 2024 first-rounder is a solid 3-point shooter, and the Celtics like to launch more deep balls than any other team in the NBA. All three of these players are under contract for the long run. Boston isn't looking to contend without Tatum as much as it will look to win upon his return, so swapping an expiring contract for three long-term rotation options makes sense.