Ten thoughts on how the Raptors could respond to the loss of Fred VanVleet, including a Pascal Siakam trade

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*Extreme Kylo Ren voice* Kill the past!

Or at least let’s not repeat the same mistakes of the past. That should be the Raptors’ goal coming out of a disappointing first four hours of free agency that was largely the result of a flawed process this year — from poor self-evaluation to player evaluation.

In itself, losing Fred VanVleet for no return is not a disaster, except for the flexibility to pay Dennis Schröder. We don’t know exactly what the Raptors could have gotten for VanVleet at the trade deadline, and while any future equity would have been preferable, that value would have been diminished if they also had to take on unwanted contracts to make a trade work. (Jake Fischer of Yahoo reported Phoenix and the Clippers as VanVleet suitors, but that probably would have meant taking back Marcus Morris or Landry Shamet or some other player they’d rather not have.)

However, the overvaluation of their own players led the Raptors to commit to a plan to remain in win-now mode, even though it would have been ideal to maintain freedom of choice. It also means they may have missed their best opportunities to trade some of their best players who may or may not intend to stay in Toronto long-term.

The lesson: Surrender leverage and control at your peril. If nothing significant changes with their roster or the contractual status of their top players within the next year, the Raptors will enter free agency with three of their top six players on the market: Gary Trent Jr., OG Anunoby and Pascal Siakam. Scottie Barnes will also become eligible for a rookie extension.

Let’s get specific, shall we?

1. VanVleet’s departure only makes it that much clearer, at least to me: The Raptors should seriously explore trading Siakam. With the downgrade at point guard (and yes, it’s a downgrade), the Raptors are a less dangerous team. Siakam’s market might not be what the Raptors want, especially with his agency leaking, he won’t consider signing an extension with a team he’s traded to, and Portland isn’t a viable Siakam destination with the Damian Lillard trade request.

Still, there’s very little shooting on this roster, and that will limit: a) how big Siakam can be; and b) how much Barnes is capable of growing. Siakam and Anunoby are the two means of getting some real help and roster diversity for Barnes going forward.

2. The question the Raptors have to ask themselves is whether Siakam is more valuable now, in the final year of his contract with questions about whether he would consider signing an extension with the acquiring team or a four-year deal of $192 million with the Raptors starting next year. It’s not a rhetorical question, by the way. There are issues of fit that complicate it. Also, if Siakam doesn’t take the extension now from the Raptors, that’s a moot point. Trade him now so you don’t risk a repeat of the VanVleet situation.

3. Who might be interested in Siakam? Atlanta, Oklahoma City, Brooklyn, Chicago, Indiana, and Minnesota all make varying degrees of hypothetical sense. I’d encourage the Raptors to focus on the future rather than the near term, but there’s no need to limit your search.

4. Say it with me: The first round pick the Raptors gave up for Jakob Poeltl is a sunk cost. Not having it should not be a guiding principle of the franchise. Maximizing the potential of your best young players should be the goal here. If it comes with being a non-playoff/play-in team, so be it. If they lose a pick in next year’s draft that the Raptors and many other experts consider weak, that’s part of the calculated risk the team took when it traded for Poeltl. The pick is top-six protected. If not conveyed, it would be a 2025 election with the same protection.

5. I would be less inclined to trade Anunoby, but the Raptors need to take stock of what happened last Friday. The Trail Blazers gave Jerami Grant a five-year deal worth $160 million, making any vague notion that Anunoby will sign the four-year, $117 extension offered to him by the Raptors. It does not happen.

It is therefore incumbent upon the Raptors to find out what Anunoby wants on the court. If that’s not available in Toronto, even after VanVleet leaves, then it’s time to move him. Financially, the Raptors must be prepared to pay Anunoby a max-value deal if it comes to that. What, you’re saying Anunoby isn’t worth such a deal? Look what just happened to VanVleet. More teams will likely have cap space next year with the free agency class likely better than this year. If you balk at the price, get what you can and move on. Anunoby is young and good enough to be a part of the Raptors future, but he has to want to be in this situation.

6. If nothing significant changes, I would assume the starting lineup would be Barnes, Trent, Anunoby, Siakam and Poeltl, with Schröder coming off the bench. If possible, the Raptors should still try to go out and acquire a guard with somewhat more catch-and-shoot 3-point ability than Schröder. Even if the Raptors want to hand the keys to Barnes and Siakam, they could still use an organizer with secondary creation ability to take the ball-handling pressure off the forwards.

As for who it is, there aren’t many obvious targets. Boston’s Peyton Pritchard would be pretty perfect, but it sounds like the Celtics are intent on keeping him. Boston could be looking to move on from Malcolm Brogdon, but even with Brogdon’s injury issues, it will probably take more than Chris Boucher and Thaddeus Young to get that deal done. The healthy version of Brogdon would be great for that role.

7. Here’s an interesting thought experiment: Brogdon for Gary Trent Jr. and Malachi Flynn. The Raptors would have to be OK with Brogdon’s physicality and it might be a non-starter. In addition, they are getting significantly older. However, you get the type of guard play you need to help Barnes on his way, and remove a player you have to pay long-term or risk losing for nothing, along with Barnes and (hopefully) Anunoby. Boston is coming off another year of guaranteed money, which will be important when Jaylen Brown’s likely extension kicks in, and a look at a young player who can provide some of the shooting the Celtics would lose.

8. The logic of the above trade depends on what you think of the idea of ​​offering an expansion to Trent, which would be very similar to the one they can offer Anunoby. Trent turns 25 in January, so he’d obviously fit nicely along a Barnes-centric timeline. He could easily be much better than he is at the moment. So far, he would have to show either improved play or defense to be a quality starter. A salary of around $25 million annually should settle into quality starter money in the short term.

I’m just not sure if Trent will turn out to be that type of player. He slipped significantly on defense last year, and he was just a high-risk, high-reward defenseman before. His assists also slipped slightly on a per-minute basis. Trent is a good NBA player, but I’m not sure the Raptors should pay that much for a guy whose best role is probably as a sixth man. Regardless, Bleacher Report’s Chris Haynes reported for the second time on Friday that The Raptors and Trent are working on an extension, which cannot be officially offered until the two-year anniversary of him signing his previous contract. As that deal was made in August 2021 due to the delayed start of the 2020-21 season, there is a corresponding date (that I don’t know) when the two sides could agree an extension this month.

9. Speaking of quality starters, the Poeltl contract is fine. He’s a quality player and only 28. As evidenced by Boston’s attempt to trade for him at the deadline as well, he’ll likely be valued by winning teams over the course of his deal as long as he stays healthy.

10. With Young’s contract guaranteed on Saturday, the Raptors now have 13 players signed to major league deals. Without knowing the exact details of Poeltl’s and Schröder’s deals, I can only estimate that they will make around $156 million combined, giving them $9 million or so to fill out the roster, with two spots open. Those 13 players: Siakam, Poeltl, Anunoby, Trent, Schröder, Boucher, Barnes, Young, Otto Porter Jr., Precious Achiuwa, Flynn, Gradey Dick, and Christian Koloko. Aside from any minimum contracts, they could still use the semi-annual exception, which could be one or two years long and start with a salary of $4.5 million.

The Raptors also have Joe Wieskamp under contract. His $1.93 million salary guaranteed on July 18. They have qualifying offers out to last year’s 2-way players, Ron Harper Jr. and Jeff Dowtin Jr. If these players accept the qualifying offers, they would remain as two-way players.

Given the Raptors’ history, the best bet is that they give them small guarantees and allow them to compete for key spots in training camp, opening up the other two-way spots for new players besides Markquis Nowell, the Kansas State point guard they agreed to about, shortly after the draft happened.

(Top photo by Fred VanVleet and Pascal Siakam: Mitchell Leff/Getty Images)

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