Raptors May Regret Not Making This Trade

It's been nearly a month since the NBA trade deadline, and the Toronto Raptors didn't shake things up very much at all.

The Raptors made a small deal with the Golden State Warriors, acquiring Trayce Jackson-Davis in exchange for a second-round pick in the 2026 NBA Draft. The Raptors nearly traded RJ Barrett to the Sacramento Kings for Domantas Sabonis, but talks fell through.

Bleacher Report writer Andy Bailey believes the Raptors should have traded Barrett to the Chicago Bulls for Anfernee Simons after he was dealt by the Boston Celtics.

"You don't see too many one-for-one swaps in the NBA these days, but RJ Barrett and Anfernee Simons have played at roughly the same level this season and are within a year of each other in age," Bailey wrote.

"Barrett is bigger and theoretically more switchable on defense, while Simons is a far more reliable and higher-volume shooter.

"And what sets each player apart from the other could help the respective teams landing them.

"The Chicago Bulls have a glut of guards after the trade deadline. Upsizing at least one of those roster spots to a forward makes sense. And the Toronto Raptors already have much of Barrett's skillset covered by Scottie Barnes and Brandon Ingram. What they need, as evidenced by their 24th-ranked three-point percentage, is Simons' jumper."

Raptors Could Have Traded For Anfernee Simons

Toronto Raptors forward Brandon Ingram dribbles past Chicago Bulls guard Anfernee Simons. | Dan Hamilton-Imagn Images

Trading for Simons would have been tricky for the Raptors because he is on an expiring contract. While Barrett and Simons are close in production, their contracts do not reflect that.

It would not have been wise for a team like the Bulls to bring in Barrett when their whole plan was to acquire expiring deals. If the Raptors wanted to make a trade with the Celtics for Simons before the Vucevic deal came into the picture, that also wouldn't have made sense because Toronto didn't have a big man to trade.

Perhaps the Raptors will target Simons in free agency this summer to give them that 3-point shooter the team needs. Simons should have a competitive market, but the Raptors might make sense as his next destination.

In the meantime, the Raptors will face off against the Minnesota Timberwolves tomorrow at 8 p.m. ET inside the Target Center in Minneapolis. Fans can watch the game on Sportsnet or stream it on NBA League Pass.

Sign up for our free newsletter, which will bring all Toronto Raptors On SI stories every weekday to your email.