The Toronto Raptors missed the playoffs this year for only the second time since the 2013-2014 season. They have a very interesting offseason ahead of them where they can take the franchise in two vastly different directions. They could go the win-now route, or they can choose to start a rebuild around Scottie Barnes. They have the free agencies of Fred VanVleet and Gary Trent Jr. to decide, so it will be interesting to see if the Raptors attempt to run it back or if they let both players walk. With that said, here are three trades the Raptors should consider making this offseason.

1. OG Anunoby to the Grizzlies

Days before the trade deadline, rumors circled that the Grizzlies wanted to upgrade at the small forward position. The Grizzlies’ top two candidates at the time were Mikal Bridges and OG Anunoby. Now that Bridges has a new home in Brooklyn, it’s safe to say he is off the table for trade. The Grizzlies need to make a move to put them closer to championship contention by going after a reliable three-and-D guy like Anunoby, who might be exactly what they need. For the Raptors’ side of things, if they are trying to go into rebuild mode, then trading Anunoby for picks may be the perfect start. The trade could look something like this,

Raptors receive: Dillon Brooks (in a sign and trade), Kenneth Lofton Jr., the 2024 Warriors' top four protected first-round pick and the 2024 Grizzlies' top 10 protected first-round pick.

Grizzlies receive: OG Anunoby.

2. Pascal Siakam to the Trail Blazers

If the Portland Trail Blazers want to keep Damian Lillard, they need to make a move to go after an all-star. A Pascal Siakam and Lillard pairing may be the perfect match and may be able to put them back in championship contention with the right pieces around them. For the Raptors side of things, trading Siakam accelerates a rebuild and would make Scottie Barnes the head of the team going forward. The trade could look like this,

Raptors receive: Anfernee Simons, Nassir Little, Keon Johnson, and the number three pick in the 2023 NBA draft.

Trail Blazers receive: Siakam and Precious Achiuwa.

3. Deandre Ayton to the Raptors

If Toronto decides they do not want to rebuild and instead want to be a playoff contender, going after Ayton would give them a much better chance at making some noise in the playoffs. To make this trade make sense for the Suns a three-team trade would have to occur to give the Suns the extra depth they so desperately needed in this year's playoffs. The Hornets would be the third team in this scenario and would trade for Jakob Poeltl in a sign and trade to help the Hornets become more competitive next season. The trade would look like this,

Raptors receive: Deandre Ayton.

Suns receive: Gordon Hayward, Otto Porter Jr., Dennis Smith Jr., Achiuwa, the number 13 pick in the 2023 NBA draft (Via Toronto), a 2024 second-round pick (Via Charlotte), and a 2025 second-round pick (Via Charlotte).

Hornets receive: Poeltl (Sign and Trade).