Ah yes, the enigma that is the Toronto Raptors. The Raptors are entering a new era, with two pillars of their championship-winning 2019 team in Fred VanVleet and head coach Nick Nurse deciding to find greener pastures south of the Canadian border. With this transition comes a few questions as to whether president of basketball operations Masai Ujiri will now be more willing to move his established veterans Pascal Siakam and OG Anunoby, among others, with the intention of hitting the reset button and building around Scottie Barnes.

Alas, the team's offseason moves say otherwise. The Raptors re-signed Jakob Poeltl, which was a must given what they traded away for him, and acquired Dennis Schroder, the 2023 FIBA World Cup MVP, to replace VanVleet as the team's starting floor general. So it stands to reason that the Raptors, as ill-fated as it could end up being, will be staying the course, especially when Siakam has said in the past that he's more than willing to re-sign with the team.

Nevertheless, there are still a few loose ends the team may need to tie up to put themselves in a much better position to sneak into the playoffs in the coming season. With that in mind, here are two trades the Raptors could make.

The long-overdue Gary Trent Jr. trade

Raptors trade away Gary Trent Jr. to the Los Angeles Clippers for Marcus Morris Sr. and three second-round picks

For much of the 2022-23 season, Gary Trent Jr. was on the chopping block for the Raptors. Given his contract situation and waning role, it made sense for the Raptors to cash in on Trent as a trade asset, with the Los Angeles Lakers reportedly in pursuit of the 24-year old shooting guard.

In the end, the Raptors were stubborn, as they preferred to keep their core intact through the trade deadline in the hopes of bouncing back in the second half of the season. And to an extent, they did: the addition of Jakob Poeltl helped stabilize the Raptors, and they made the play-in tournament, losing to the Chicago Bulls in the 9/10 game.

However, one couldn't help but feel like the Raptors missed a chance to add more draft assets or young prospects for the measly prize of making the play-in tournament. The departure of Fred VanVleet in free agency is heartbreaking in that regard, as the Raptors could have recouped some value for him instead of watching him walk for nothing.

With Gary Trent Jr., there was a possibility that the Raptors could have lost him for nothing as well. But the market wasn't exactly hot for Trent, so he decided to opt into his contract so he could perhaps play his way into a bigger contract. Now, the Raptors have a second chance to trade Trent for draft assets — which they should take if the opportunity presents itself.

It's difficult to envision the Raptors receiving a first-round pick in return for Trent, given his impending free agency. But there's room for a contending team to add Trent — with the Clippers perhaps finding it beneficial to add him if they lose Norman Powell in the inevitable James Harden trade.

Due to the Clippers' lack of leverage with trading away Marcus Morris Sr., the player who has fallen out of favor with the team's fanbase, the Raptors should squeeze as many second-rounders as they could from them. In this case, they'll be getting three.

Morris is an expiring contract, and on paper, he could provide the Raptors with more spacing at the forward positions. Trent's departure could also pave the way for more touches for Gradey Dick — a player whose development the team should be prioritizing.

Filling a need at guard

Raptors receive Terry Rozier from the Charlotte Hornets for Thaddeus Young, Otto Porter Jr., Malachi Flynn, and four second-round picks

Armed with three more second-rounders from the Gary Trent Jr. trade above, the Raptors use them to pursue Terry Rozier to give the team more scoring punch and ballhandling creativity at the point — a position that remains extremely thin for the Raptors.

It's fair to wonder whether it's the best use of assets to trade for Rozier instead of just keeping everyone and Trent instead. But Rozier is a much more dynamic pick-and-roll threat than Trent, an audacious pull-up artist who keeps defenses honest and someone who can be an annoying defensive pest if need be.

Rozier may not be the most efficient scorer ever, but he's undoubtedly a better player than Trent is due to his shot-creation abilities. The Raptors have a hole to fill in that department in the aftermath of Fred VanVleet's departure, so trading for Rozier should be perceived as more than just a lateral move.