Toronto Raptors president Masai Ujiri and the front office always seem to have an ace up their sleeves when it comes to improving the team's roster during the offseason. Just looking back a few years, they shocked everyone by moving DeMar DeRozan in a trade for Kawhi Leonard, a deal that ultimately led to their first title in franchise history. Holding onto talent during the summer has never been the Raptors' forte, though, and they once again lost a key part of their roster in the offseason.

Losing Leonard to free agency in 2019 and then Kyle Lowry in 2021, Toronto failed to retain All-Star Fred VanVleet this offseason, as he was one of the better unrestricted free agents available. The Raptors found themselves in a bidding war for VanVleet over the summer with the Houston Rockets. Things were trending in the Raptors' direction, but more money and the opportunity to be “the guy” in Houston ultimately lured the long-time Raptor away.

Entering the 2023-24 season, the Raptors no longer have VanVleet and they are looking to get back to the playoffs with a first-time head coach in Darko Rajakovic. As a result of missing the postseason in the play-in tournament, Toronto decided to move on from Nick Nurse this offseason. Not long after, Nurse was hired by the Philadelphia 76ers.

Stability is the problem with the Raptors right now. Frustrations always existed in this locker room last season and while they've been aggressive in the past, this front office has become somewhat passive with their unwillingness to relinquish assets. Scottie Barnes has been made unavailable, OG Anunoby's asking price is way too high, and there have been conflicting feelings about giving up All-Star Pascal Siakam.

At some point, the Raptors are going to have to make a decision whether to keep what they have and try to compete in the Eastern Conference or simply start over. Toronto will not be able to do both and the 2023-24 season may very well prove this theory.

Raptors offseason additions and departures

Rockets' Fred VanVleet with Raptors players Dennis Schroder and Gradey Dick

Additions: G Dennis Schroder (free agency – LAL), F Jalen McDaniels (free agency – PHI), G Gradey Dick (draft)

Departures: G Fred VanVleet (free agency – HOU), G Dalano Banton (free agency – BOS)

Losing Fred VanVleet was not something the Raptors were really prepared for. They knew there was interest from rival teams and that he would receive other offers, but the Raptors truly believed that their All-Star was going to be returning. With all the instability that exists and their lack of success last season, VanVleet jumped ship and took the money when presented to him.

Quite honestly, nobody can really blame VanVleet for making this decision, as nobody in the world would ever turn down a $130 million contract unless there was a better offer out there!

When the Raptors lost their starting point guard, they were not left with many options. Toronto did not have a max contract slot and many of the high-impact guards were already off the market after signing deals in free agency. With Dennis Schroder available, the Raptors turned to the recent Los Angeles Lakers guard as a possible solution.

In 66 games in Los Angeles last season, Schroder averaged 12.6 points and 4.5 assists per game while shooting 41.5 percent from the floor. Known for his quick burst and ability to draw fouls on the drive, Schroder will be able to provide the Raptors with a sense of comfortability, especially if they utilize him on their bench.

Jalen McDaniels was another name Toronto added this offseason, as he signed a two-year, $9 million contract after being traded from the Charlotte Hornets to the Philadelphia 76ers last season. A lengthy forward who has the potential to grow into a viable two-way threat, McDaniels fits the mold of athletic wings the Raptors like to add.

In the NBA Draft, Toronto surprised many when they selected Gradey Dick, arguably the best perimeter shooter in the draft class. The rookie swingman is going to be a work in progress for the Raptors, especially if they hope to utilize him on both ends of the floor.

This offseason certainly presented change to the Raptors as an organization. No big-name players want to go to Toronto in free agency and losing VanVleet could have devastating effects on their ability to earn a playoff spot.

2023-24 season outlook

Raptors players Pascal Siakam with OG Anunoby

It seems like it is a matter of time before the Raptors make another big roster adjustment. The only question is will this involve a major addition or a major departure?

Siakam's name was connected to the Atlanta Hawks this offseason and the Raptors did receive a handful of offers for the superstar. Anunoby is another player who has come up in trade conversations, as various teams reached out to Toronto ahead of last season's trade deadline to inquire about him.

As the Raptors prepare for the 2023-24 season, Siakam enters the final year of his contract and is extension-eligible. For Anunoby, he owns a player option he could utilize to become a free agent in 2024. Then there is Barnes who becomes extension eligible next offseason.

Toronto is going to need to open their checkbooks if they are to retain all three players on new, long-term contracts, which is why it's plausible to believe that change is inevitable. It's also worth mentioning Gary Trent Jr. and his potential departure as well. Trent was supposedly close to an extension with the Raptors this offseason as he enters the final year of his deal, yet no new contract was ever signed.

All the uncertainty surrounding the Raptors is starting to add up, which is why it's hard to believe they will improve from their 41-41 record during the 2022-23 season. Time will tell if the Raptors can once again be threats in the Eastern Conference or if they will inch closer toward an all-out rebuild.