Can the Celtics find a way to make a solid trade in order to make the most of this upcoming season with Jayson Tatum on the court? Despite heading into last season as the NBA champions and favored to make it out of the Eastern Conference, Tatum and the Celtics ended up losing to the New York Knicks in the second round of the playoffs.
Since the Celtics already had an overpaid roster, many knew that keeping their championship squad intact was highly unlikely. Soon, trades started materializing, and now there is no real way to know what the Celtics will be capable of doing next season. In this time of uncertainty, the Celtics’ fanbase believes that the organization should be proactive.
What Should the Boston Celtics Do With Anfernee Simons?
Although Jrue Holiday accomplished much in his short tenure with the Celtics, the organization decided to trade him away to the Portland Trail Blazers in return for Anfernee Simons and two future second-round draft picks.
This trade allowed the Celtics to enter a “mini rebuild” in this short timeframe without Tatum on the court. While Simons has yet to play in his first game with the Celtics, some believe that engaging in a trade with the Chicago Bulls would be the smart move to make.
According to this hypothetical trade scenario posted by Dan Greenberg, the Celtics would get back Coby White and Jalen Smith in return for trading away Simons to the Bulls. Since their contracts match, this potential trade gathered a fair amount of interest on social media.
Now this would work! https://t.co/xe1yZNCGvZ pic.twitter.com/6SNWGQ31PR
— Dan Greenberg (@StoolGreenie) August 13, 2025
However, some fans were quick to point out that this would be an unfair trade. While trading Holiday for Simons made sense, the Bulls have no reason to trade away two young stars in return for one, especially since White is a fan favorite with the Bulls’ fanbase.
Perhaps this trade scenario is unnecessary. After all, Simons has yet to prove his value on a team with significant expectations, such as the Celtics. He is also currently in the last year of a four-year contract worth $100 million that he signed with the Blazers.
Since Simons will be an unrestricted free agent next season, it is safe to say that a lot of eyes will be on him. The Celtics will have to move fast and make a choice between signing him on for the long run and trading him away before he becomes an unrestricted free agent.