Heading into free agency, the Toronto Raptors found themselves in a unique position.

After doing much of their roster-building shopping last season, trading for Immanuel Quickley, RJ Barrett, Kelly Olynyk, and Ochai Agbaji, the Raptors weren't expected to be major players in the open market, but fans still wanted to see some positive steps forward in the team's process, if for no other reason than to prove that Masi Ujiri had a concerted plan to build the team into the future, especially after trading away a first-round pick at the 2024 NBA trade deadline, instead of flipping over the open sign to start a fire sale.

Fortunately, fans were afforded that very sign before they could say Utah Summer League, with Ujiri officially signing the belle of his 2023-24 acquisition streak, Quickley, to a five-year, $175 million contract that will effectively make him one of the faces of the franchise heading into the future.

Originally drafted with the 25th overall pick in the 2020 NBA draft, Quickley immediately found a way to contribute to the Knicks right out of the gate, averaging 11.4 points, two assists, and 2.1 rebounds a game as an energized sixth man off the bench. From there, Quickley rapidly worked himself into a bigger role for the Knicks, increasing his points-per-game averages in each passing season but remaining a reserve in New York, recording just 27 starts over his three-and-a-half seasons with the team.

After being acquired by the Raptors, Quickley immediately began starting for his new team and looked like a natural in the role, averaging the most points, minutes, field goals, and three-point attempts of his career while keeping his turnovers below two and his deep accuracy at 39.5 percent. Quickley looked like a natural with the ball in his hands as a lead guard and was able to dish out easy looks to his new teammates as a full-time point guard, with 6.8 assists per game now locked in as his career-high, nearly double his previous top average.

Could Quickley have left Toronto in free agency this summer? No, even if some other team wanted to sign the Kentucky guard to a new contract in restricted free agency, the Raptors could have matched any offer sheet that came their way. Still, if Quickley really didn't want to be a member of the Raptors long-term, he could have played out his current deal and tested the market next season, as there is no way to “franchise tag” a player who wants to leave in the NBA. While the price was certainly of market value, being able to secure his services for the next half decade is a massive win for the Raptors and fans of Toronto's lone remaining NBA team, which, considering how the Kawhi Leonard free agency played out a half-decade ago, if far from a guarantee in unrestricted free agency.

Toronto Raptors guard Immanuel Quickley (5) handles the ball against the Brooklyn Nets during the fourth quarter at Barclays Center.
Brad Penner-USA TODAY Sports

Immanuel Quickley got a much bigger bag from the Raptors

Speaking of Quickley's contract extension, before he was traded to the Raptors as one of the focal points of the OG Anunoby trade, the New York Knicks offered the combo guard out of Kentucky a much lower contract number per year than what Ujiri was willing to offer, with the cap number roughly half of what he ended up earning from Toronto.

Discussing Quickley's market last November on HoopsHype, Michael Scotto revealed that the Knicks offered up a deal at roughly $18 million a year, which is notably lower than his $35 million annual earnings from Toronto.

“The New York Knicks have a glut of guards, and rival teams are monitoring whether Immanuel Quickley will become available on the trade market after both sides failed to agree to an extension before the season,” Scotto wrote. “Quickley was offered around $18 million per year in extension talks, league sources told HoopsHype. However, Quickley was looking for closer to $25 million annually, league sources said.”

Now granted, is there a reason why a player like Quickley would be willing to sign a contract with a lower per-year average to help play for a “better” team, as opposed to a squad that may not return to the playoffs until Year 3 or even Year 4 of that five-year contract? Sure thing, Jalen Brunson literally did that exact same thing with the Knicks this week, leaving as much as $100 million on the table to help his team out, but considering how things shook out in New York and in Toronto, it's safe to say Quickley is very happy with his massive contract bump heading into the future, as he got as much as $100 million more from the Raptors than what was on the table from Leon Rose and company.