Kyle Lowry is the first domino for the Raptors in free agency | The Star
The best move would be to re-sign Lowry, to ink Gary Trent Jr. to a long-term deal (like Lowry, Trent is Toronto’s own free agent and the money is not an issue) and spend the mid-level exception to address needs at centre. That would leave a core of Lowry, Fred VanVleet, Trent, Malachi Flynn, OG Anunoby, Pascal Siakam, first-round draft pick Scottie Barnes and Chris Boucher develop.
But it’s not all up to the Raptors because if Lowry wants to move on, he will.
That’s where it gets complicated.
And for as good as team president Masai Ujiri and general manager Bobby Webster have been with draft picks, their free-agent record is spotty. None of their last four signings — Rondae Hollis-Jefferson and Stanley Johnson in 2019, DeAndre Bembry and Aron Baynes in 2020 — had any significant impact and the front office can’t miss like that again.
The big men available — and, as always, money and other offers will come into play — are the likes of Sacramento’s Richaun Holmes, Cleveland’s Jarrett Allen, Houston’s Kelly Olynyk and the Knicks’ Nerlens Noel.
That’s probably how they should be ranked, given the players’ circumstances and the likelihood Toronto could get them. None are all-star calibre and most wouldn’t be too costly but making the right choice, and convincing the right choice to come, is paramount. After whiffing on two straight summers, a third bad one in a row would be a setback.
Trent is the other wild card under Raptors control. If the Raptors keep Lowry, they basically have to keep Trent because of the financial restraints they’ll be under with only the mid-level exception to fill a handful of roster spots.
But if Lowry goes for no return, there might be a shooting guard like Charlotte’s Malik Monk who would be attractive and gettable, while still leaving Toronto to fill its frontcourt hole.
It doesn’t make much sense to spend a ton of money on a point guard to replace Lowry if he goes, given the presence of VanVleet and Flynn and the need to fill other gaps in the roster.
Bringing back two of Khem Birch, Yuta Watanabe, Freddy Gillespie and Bembry is a logical way to round out the roster but their salaries won’t have a great impact on the larger free agency picture and getting those deals done is not a priority.
The first domino is Lowry and everything will stem from what happens with him.
He will have legitimate suitors. Miami, Dallas and New Orleans — likely in that order — would be attractive destinations and all could clear cap space to make a serious run at him.
Philadelphia is another possibility but that would take a sign-and-trade transaction that would hard-cap the Sixers, who have the Ben Simmons mess to clean up as well.
There will be a level of collaboration between the Raptors and Lowry if he wants to leave, but only to a degree.