When Masai Ujiri and the Toronto Raptors front office made the tough decision to part ways with DeMar DeRozan in favor of trading for Kawhi Leonard in 2018, they envisioned a path to competing for a championship. Well, Ujiri was right, as the Raptors went on to defeat the Golden State Warriors and win the 2019 NBA Finals. Since then, things haven't been great for the Raptors. Kyle Lowry, Fred VanVleet, OG Anunoby, and Pascal Siakam have all departed in recent years, leaving the Raptors with an assortment of secondary talents to try and build with.

Scottie Barnes, the 2021-22 NBA Rookie of the Year, has been the face of the franchise over the last few seasons. With Siakam no longer leading the charge, Barnes assumed the No. 1 role in Toronto during the 2023-24 season. Alongside the former fourth overall pick, the Raptors have Immanuel Quickley and RJ Barrett helping lead the charge. Despite Barnes, Quickley, and Barrett all being talented players, the Raptors as a whole have had trouble building their identity.

In his first season as head coach, Darko Rajakovic was thrown into a situation where the organization didn't know whether they were rebuilding or attempting to contend in the Eastern Conference. Ultimately, Toronto finished the season with a 25-57 record, their fewest wins since the 2011-12 season, when the franchise only recorded 23 victories.

The Raptors are preparing for the 2024-25 season with the same core group they had a season ago, but the difference is that Rajakovic and his staff are spending a lot of time focusing on player development. This team as a collective is still fairly young and inexperienced when it comes to playing in the postseason, which is why this small rebuild that the Raptors are going through will ultimately take time. That is why this organization didn't really look to make a big splash in NBA free agency.

Overall, the Raptors were limited in terms of what they could achieve this offseason in free agency. Barnes was eligible for a massive extension, and Quickley was a restricted free agent. Awarding both players new contracts was a given, but could these decisions come back to haunt the Raptors moving forward?

Scottie Barnes' long-term potential

Toronto Raptors forward Scottie Barnes (4) dunks for a basket against the Brooklyn Nets in the first half at Scotiabank Arena.
Dan Hamilton-USA TODAY Sports

After moving on from Siakam and Anunoby, it became clear that the Raptors were going to be investing their future in Scottie Barnes. That is why Toronto gave Barnes a five-year, $224 million max contract that keeps him in a Raptors uniform through the 2029-30 season. It is pretty safe to say that Barnes is the player the Raptors want to try to win with right now and in the foreseeable future.

However, this is a lot of money for the Raptors to give a player who hasn't really proven that he can be the No. 1 option on a team.

Barnes is a terrific player — don't let that get lost in translation. The problem the Raptors now face after making this move in free agency is the fact that Barnes is going to be making an average annual salary of nearly $45 million. Although Barnes has proven to be a great defender and a point-forward who can bring the ball up the floor to initiate the Raptors' offense, he has yet to show signs of being a top-scoring option through his first three seasons.

If Barnes doesn't get better offensively, specifically as a perimeter shooting threat, his upside will be severely limited. That is where the concern and possible mistake lie for the Raptors.

Nonetheless, there wasn't much doubt surrounding the organization giving Barnes this contract. In addition to being their best player this past season, Barnes has the ability to be a triple-double-like threat whenever he plays. That is why the Raptors hold such high belief in the 23-year-old to help lead them into the future.

It is hard to say that the Raptors made a mistake by giving Barnes this extension because he has certainly earned it. The only question at hand regarding Barnes and his long-term future with the Raptors is if he can truly live up to the expectations that have now been placed on his shoulders after earning the largest contract in team history. This is certainly a risk that the Raptors have taken.

Raptors locked down on long-term contracts

2024 free agent point guard Immanuel Quickly on the Raptors
Jim Rassol-USA TODAY Sports

Aside from giving Barnes a massive extension, the Raptors also gave Immanuel Quickley a five-year, $162.5 million contract after he stood out as the team's lead point guard after acquiring him from the New York Knicks.

Quickley has always been a gifted scorer in the NBA. When he was with the Knicks, the young combo guard was mainly utilized off the bench as a shooting threat who could create scoring opportunities for himself. With the Raptors, Quickley only expanded his offensive game due to the fact that he became their lead guard next to Barnes.

Much like the decision to extend Barnes, the Raptors didn't have to think that hard about whether or not they wanted to keep Quickley around.

After giving Quickley and Barnes their new contracts, the Raptors now have both players under contract through the 2028-29 season, meaning that these are the two players the organization believes in the most as far as becoming a contending threat once more goes. We can even throw RJ Barrett in the mix as being under contract long-term, as he is going to be with the Raptors through the 2026-27 season.

Essentially, the Raptors have tied up a trio of players that can really play off one another offensively. While every organization searches for stability and a young core like the Raptors have built, Toronto is in a risky position because of the cap hits these three players incur. Although they will only combine to collect 48.6 percent of the team's total cap during the 2024-25 season, the Raptors' trio will be collecting almost 64 percent of the team's total cap during the 2025-26 season.

The constant increase in salaries and the near $100 million per year that the Raptors will owe Barnes, Quickley, and Barrett over the next couple of seasons tie this organization up financially. While they have no thoughts of moving him, Barnes is essentially an asset who can't be moved because of the size of his contract. It would also be extremely tough to find a suitor for Quickley's big deal if things didn't pan out as Ujiri and this front office imagined.

This offseason and the NBA free agency period definitely present future risk to the Raptors. None of the moves they have made should be classified as mistakes at this time, but two or three years from now, the Raptors may be looking back at the 2024 offseason and kicking themselves for these decisions.