Raptors have plenty to figure out before trade deadline

There are decisions coming in Toronto. There are decisions to be made across the NBA, but plenty of front offices will hold their cards in this months-long game of poker and never let go. It appears clear the Raptors, who have been reluctant to ante in recent seasons, won’t choose to stay silent before the Feb. 9 trade deadline sounds.

“What they’re not gonna do is be in the middle,” said one Western Conference executive.

“They’ve told teams they’re going to do something,” said an assistant general manager.

All throughout the G League Showcase in late December, Toronto officials informed inquiring minds they’ll evaluate this Raptors roster until that fateful second Thursday of next month, league sources told Yahoo Sports, especially as head coach Nick Nurse’s unit stands at just 20-24, tied for 10th in the conference, with a roster Toronto leadership expected to compete among the Eastern elite. Those are the standards when you’ve landed a youngster such as Scottie Barnes, whom the Raptors wouldn’t entertain dealing for Kevin Durant this past summer, and All-Stars like Pascal Siakam and Fred VanVleet.

The stability atop the Raptors’ basketball operations has rival executives and player representatives bracing for some type of change. We have seen large swings from team president Masai Ujiri and GM Bobby Webster’s front office before, with the backing of a deep-pocket ownership group and Maple Leaf Sports chairman Larry Tanenbaum. If Toronto decides to bolster this group, league personnel expect the Raptors to focus on playmaking on the perimeter and rim protection in the interior.

They have certainly sniffed around the big man market in recent seasons. Toronto engaged Dallas about acquiring Kristaps Porzingis for Goran Dragic and the first-round draft pick ultimately sent to San Antonio for Thaddeus Young. The Raptors registered interest in Rudy Gobert this past summer, sources told Yahoo Sports, although there was never a serious approach from Toronto. Myles Turner and Deandre Ayton have been two other centers on Toronto’s radar, sources said. And former Raptors center Jakob Poeltl, who left the franchise with DeMar DeRozan as part of a 2018 offseason blockbuster to land Kawhi Leonard, remains a target of Toronto’s front office, as Yahoo Sports reported in December.

TORONTO, ON, CANADA - January 12, 2023:     Gary Trent Jr. #33 of the Toronto Raptors before the Toronto Raptors v Charlotte Hornets NBA regular season game at Scotiabank Arena in Toronto (Photo by Anatoliy Cherkasov/NurPhoto via Getty Images)
Gary Trent Jr. is in position to decline next season’s $18.5 million player option and test free agency. (Photo by Anatoliy Cherkasov/NurPhoto via Getty Images)

But if the losses keep piling, and the Raptors steer in the direction of the Tampa Tank that netted Barnes at No. 4 in the 2021 NBA Draft, Toronto will have no shortage of buyers in this current seller’s market. Plus with the standings so deadlocked in the middle, the franchise is just as close to the top tier of the draft lottery as it is to the backend of the postseason, without a full-fledged fire sale required to vie for another high pick.

Could the Raptors ultimately decide to trade Siakam? Anything is possible in this world of Musical Chairs, but Toronto is expected to seriously listen to offers only for Gary Trent Jr., sources said. VanVleet’s apparent trade candidacy seems far more rooted in his down performance this season, as the smaller guard approaches his 29th birthday, than the front office’s willingness to part with such a central team leader. Meanwhile, Raptors officials have left rival front offices with the impression, sources said, it would take a haul at least in the ballpark of Atlanta’s offseason price for Dejounte Murray — multiple unprotected first-round draft picks — for Toronto to even consider parting with OG Anunoby, a known favorite of Ujiri.

As Marc Stein previously reported, Trent appears to be the most likely Raptor to be traded, and by a wide margin. Various rival executives are under the impression Toronto will even search to move Trent before the deadline, as Trent is positioned to decline next season’s $18.5 million player option and test free agency. Early indications are that Trent will be seeking upward of $25 million in average annual value before the 2023-24 campaign begins.

Trent arrived in Toronto, after all, as the result of a similar dynamic with Norm Powell before the 2021 deadline. The Raptors moved Powell to Portland in exchange for Trent, as Powell was expected to decline his player option for that following 2021-22 season. The Blazers ultimately awarded Powell a five-year, $90 million contract Toronto had little interest in extending, but the Raptors did sign Trent to his three-year, $51 million deal instead.

What would the Raptors look for in return for Trent? One inkling: Toronto has shown interest in Hornets forward Jalen McDaniels, sources said. Charlotte’s fourth-year forward would fit the same bill that Trent did two years ago. He’s set to reach unrestricted free agency this summer, where teams are projecting McDaniels to command a far lower salary than Trent — roughly $10 million per season — in the ballpark of the full non-taxpayer mid-level exception.

VanVleet also faces a player option next year, which he’s similarly expected to decline, but his circumstances are more clouded. Both sides appear open to resuming contract dialogue at season’s end, sources said, after there was no significant traction on an extension this past offseason. "I will never speak on my free agency or contract negotiations, especially conversations between me and management …" VanVleet recently told reporters. "But I was never made a formal offer."

VanVleet could have extended to the tune of four years, $114 million, and by waiting, he’ll become eligible for a deal worth as high as $230 million over five seasons. That upper echelon would appear to be unrealistic. And yet VanVleet, who became just the fifth undrafted player in NBA history to reach the All-Star Game a season ago, has been playing on a below-market value deal. Anyone undrafted enters the league at a financial disadvantage, typically first earning a minimum-salary contract, where cap restrictions then limit how much players can receive in raises for their next deals. It seems quite natural for there to be added motivation from VanVleet and his representation to search for a richer payday now that he’s established himself as a top starting point guard, ahead of an anticipated cap spike from the league’s upcoming 2025 broadcast deal.

League figures are ballparking VanVleet’s next salary between $30 million and $35 million, above the threshold he could have extended for this past summer, but the length of that contract will be of note. Kyle Lowry before him did sign a three-year, $100 million agreement with the Raptors before the 2017-18 season at 31 years old.

Much of the conversation surrounding Toronto’s decision-making stems from a matter of accounting. The Raptors will have plenty of flexibility to evade the luxury tax next season, but are currently tracking toward a monstrous payroll for 2024-25 with Siakam and Anunoby each eligible to reach free agency that summer before, especially if VanVleet’s next big deal stays on their books. And at this juncture, is this Toronto team currently one that’s worth such a hefty bill? If that seems like too far in the future to consider, 2024 free agency is less than 18 months away.

Anunoby will surely be seeking his own raise just like VanVleet. The 25-year-old forward has garnered Defensive Player of the Year buzz this season while earning under $20 million annually this year and next. His situation is actually quite similar to Murray’s before him, with the All-Star point guard’s bargain contract of $16 million average annual value setting his possible extension number far below the maximum figure he’ll become eligible for in the 2024 offseason — virtually guaranteeing Murray will reach unrestricted free agency. Anunoby and Murray also share the same representation: Klutch Sports.

That is where the comparisons seem to end, though. A large factor in Murray’s departure from San Antonio was his interest in departing the franchise, and the Spurs’ conclusion that Murray would either not be worth that 2024 payday, or wouldn’t be worth it amid the team’s overall timeline of competitiveness. There has been no indication the Raptors have any ideas other than retaining Anunoby. Although he is certainly expected to decline his $19.9 million option for the 2024-25 season and reach unrestricted free agency, where any rival lined up with an offer for Anunoby will surely pitch a larger offensive role than he’s currently afforded north of the border.

“If the Raptors made him available for trade right now, every single team is going to call,” one general manager told Yahoo Sports.”

Toronto has 12 games to play between now and the deadline, an eternity in this league-wide transactional holding pattern. The results of a grueling seven-game road trip around the Western Conference, which concludes just before the Feb. 9 buzzer, may ultimately push the Raptors’ front office in its next direction.