It’s easy to look at the Raptors’ position in the standings, the number of contenders around the league and concludes the Raptors would be best served to punt on this season. From a value proposition, that is probably correct. Far more teams than usual can make legitimate cases that they can make deep playoff runs this year, and the Raptors, in 11th in the East as they enter the second half, are clearly a tier below the conference’s top-five teams, to say nothing of the additional five teams between those contenders and the Raptors. Even a 26-15 second half would still likely have them navigating the Play-In Tournament.
The Raptors, should they decide to make some of their best players available, would have some of the most desirable targets in what’s increasingly looking like a sellers’ market. The Play-In Tournament has made it harder for teams to pack it in by February, while the league’s four truly awful teams — Houston, San Antonio, Detroit and Charlotte — aren’t overflowing with talented players who they are looking to trade who could play big roles on good teams. If the Raptors made Pascal Siakam available, he would be the best player on the market, depending on how you feel about Bradley Beal and DeMar DeRozan. OG Anunoby would be the best 3-and-D wing. Fred VanVleet and Gary Trent Jr. could both start or play massive roles as third guards for a contender. No other team that is potentially a seller could offer so much to a good team.
What would being a seller look like, though? Whether it’s an intentional one-year step back (not unlike the Tampa Tank) or a complete overhaul (trading Siakam and two or all three of the other players mentioned) leading to a multi-year rebuild around Scottie Barnes and future lottery picks, it is helpful to know what pieces you might be able to get to expedite either process.
I don’t expect the Raptors will trade any of the four players until January is done. Saying that, I thought it would be a helpful exercise in order to understand what the market could yield.
A note: These are not all trades I would execute if I were in charge of the Raptors. I tried to err on the side of asking for more versus asking for less in hypothetical trades, but the idea is to give you a sense of what potential returns for the Raptors’ core pieces could look like. (And, as importantly, these should help display what is unreasonable to expect.) Likewise, my colleagues who helped me out here are considering these trades in something of a vacuum as opposed to judging them based on the entirety of the market.
We’ll start today with VanVleet and Trent, as they are in similar contractual situations. (Unlike Trent, VanVleet could still sign an extension with the Raptors before this offseason.) We’ll get to Anunoby and Siakam tomorrow, trades that would require a philosophical shift from the Raptors (and get them more in return).
(VanVleet makes $21.25 million this season, and has a player option for $22.82 million for 2023-24.)
VanVleet means a ton to the Raptors, on the court and culturally. It’s important to try to separate yourself from the second part to an extent, but not entirely: Leadership is important to any team, and VanVleet carries a ton of weight within the organization.
If you’re the Raptors, you have to look ahead to his free agency, and know what you’re willing to invest in VanVleet’s early 30s. The Raptors lost Kawhi Leonard and Danny Green in free agency 2019 because they were trying to keep a championship team together, and they lost Marc Gasol and Serge Ibaka the next offseason in part because they were trying to maintain cap room to chase Giannis Antetokounmpo in free agency in 2021. (Antetokounmpo signed an extension with the Bucks soon after.)
There is no such concern with this team. They are not a championship contender, and the front office isn’t trying to create cap space right now. While not having VanVleet on the books could help create cap space in the long-term, moving him wouldn’t help them add players in free agency in the short-term — not on its own, at least. Before this run, Masai Ujiri was known for holding on to his players, even on a sub-optimal salary, in order to not lose them for nothing.
Even in an abysmal shooting year, VanVleet is still making a positive impact on the Raptors. In order to trade him, the Raptors would probably want multiple quality cost-controllable assets (young players or picks), or a single excellent one.
To Magic: VanVleet and Khem Birch (two years, $13.65 million remaining)
To Raptors: Cole Anthony (two years, $9.15 million remaining, likely RFA in 2024), Mo Bamba (two years, $20.6 million), Terrence Ross (one year, $11.5 million) and a top-8 protected 2023 first-round pick
The Magic’s view: This has to be a no for the Magic. Orlando is not a free agent destination, and the way the Magic will break through this rebuild is through good drafts and trading for a prime free agent under contract. VanVleet is prime, but he will surely exercise that player’s option. The Magic can’t risk a pick, even a protected one, when the commodity they’re trading for isn’t a sure thing. — Joe Vardon
To Lakers: VanVleet
To Raptors: Patrick Beverley (one year, $13 million), Kendrick Nunn (one year, $5.25 million), Max Christie (two years, $2.74 million, RFA in 2024) and a 2027 first-round pick
The Lakers’ view: Yes. I think VanVleet’s (relatively) down season, particularly as a 3-point shooter, would give the Lakers some pause. They need shooting and size/length on the perimeter and in the front court. VanVleet clearly doesn’t address the latter need, but he could address the former if he returns to his career shooting norms. Regardless, he still grades out well in all-in-one metrics, and I think the talent upgrade — in terms of actual rotation pieces, it’s basically Beverley for VanVleet — is significant enough for the Lakers to say yes to the offer. — Jovan Buha
To Mavericks: VanVleet
To Raptors: Josh Green (two years, $7.86 million), Davis Bertans (three years, $49 million, including player option for 2024-25) and a 2025 first-round pick
The Mavericks’ view: Dallas isn’t expected to trade first-round picks or a young player like Green in any situation this season; the front office understands its ammunition needs to be saved for a major move in the next year or two. This isn’t the sort of deal that would tempt them. VanVleet would help the Mavericks, but he doesn’t fit their timeline and doesn’t offer the defensive upgrade they’re wanting for their 23rd-ranked defense, per NBA.com. — Tim Cato
Gary Trent Jr.
(Trent makes $17.51 million this year, and has a player option for $18.56 million for 2023-24.)
Trent will be 24 this offseason compared to VanVleet’s 29, which theoretically should make him more attractive in the free-agent market — and more attractive to the Raptors. However, he is not nearly as complete a player as VanVleet, and has a less impressive resume.
Given the weirdness of the Raptors’ last three seasons, it is still tough to judge whether Trent would work better as a starter or a sixth man on a good team. He has a limited track record as a productive starter on a good team, but clearly has the skill set to be a good scoring-minded guard in the NBA. He’s already proven it.
The league craves a bit more size and defensive flexibility from its starting wings. However, Trent has improved since his early days with the Raptors, especially to teams that value turnover creation highly, and he has room to grow. Trent could help some of the scoring-deficient contenders and, as with VanVleet, any team that acquires him also gets his Bird rights to help retain him in free agency.
To Knicks: Trent
To Raptors: Derrick Rose (one year, $14.52 million, plus team option for 2023-24), Immanuel Quickley (two years, $6.49 million, RFA in 2024), worse of Mavericks/Knicks 2023 first-round pick
The Knicks view: I don’t see the Knicks doing this one, especially with the way Quickley is starting to turn it on. He’s become New York’s best team defender on the perimeter. Trent is a quality scorer and shooter. He can get hot. But I’m not sure that’s what the Knicks need, especially considering there’s a chance he could end up a rental if he chooses not to pick up his player option this summer. Quickley, on the other hand, is still on a rookie contract for the next year and a half. — Fred Katz
To Clippers: Trent
To Raptors: Terance Mann (three years, $23.9 million), Luke Kennard (two years, $28.51 million, plus team option for 2024-25), 2028 first-round pick
The Clippers’ view: Trent coming to LA would be hilarious after he was traded to the Raptors for 2019 NBA champ and current Clipper Norman Powell. At 6-foot-5, Trent would give LA the type of defender that forces live-ball turnovers, the weakness of an otherwise strong Clippers defense. Trent is a decent 3-point shooter and a strong finisher. But this is way too much to give up for a player who can become a free agent in 2023. Mann is a valuable multi-tool player who just became the starting point guard and whose extension kicks in next year, while Kennard is the best shooter on the team. The Clippers also shouldn’t be tossing first-round picks away when they’re already paying Oklahoma City for the Paul George trade. — Law Murray
To Lakers: Trent and Juancho Hernangomez (one year, $1.84 million)
To Raptors: Beverley, Nunn, Christie and a 2027 top-8 protected first-round pick
The Lakers’ view: Maybe. I think the Lakers probably do this, depending on what else is out there. But I bet they’d push back on including Christie, who they are high on long term, or fight to make the 2027 pick lottery-protected. Trent Jr. would boost their 3-point shooting, perimeter defense and overall offensive firepower, but he’s still on the smaller side among wings. They need someone more in the 6-foot-7 to 6-foot-9 range. (Author’s note: It’s too bad the Raptors don’t have any of those guys.) I think they’d prefer VanVleet by himself, given his All-Star pedigree, or a larger deal like the next trade. — Buha
Let’s get wild
To Lakers: VanVleet, Trent and Chris Boucher (three years, $35.25 million)
To Raptors: Russell Westbrook (one year, $47.06 million), Christie, 2027 and 2029 first-round picks
The Lakers’ view: Yes. I think this trade checks multiple boxes for the Lakers, bringing in an All-Star-caliber talent (VanVleet) while adding 3-point shooting (Trent Jr.) and size/length in the frontcourt (Boucher). They’re turning Westbrook into two good starters and a solid bench big. Two first-round picks is a steep price, obviously, but if they were entertaining that package for Myles Turner and Buddy Hield, I think this deal is similarly impactful. — Buha
(Top photo: Tim Nwachukwu/Getty Images)