Raptors offseason: Talking extensions, free agency and draft with John Hollinger

With the offseason nearly here, The Athletic’s Raptors beat writer Eric Koreen and senior writer John Hollinger had a discussion about the biggest decisions facing the Raptors this offseason.

More Raptors offseason: primer | trade tiers | top-25 free agency big board | change of scenery trades | mailbag part one, part two | draft targets at 33

Koreen: Hey John. Thanks for taking the time. First, a needlessly aggressive, rhetorical question: Has Precious Achiuwa made you eat your words on the Kyle Lowry sign-and-trade deal from last summer yet? Seriously, no need to answer. Raptors fans on the Internet keep their receipts.

Before we get to the matter of this offseason, I wanted to get your general opinion of the 2021-22 Raptors season that ended a month or so ago. What were your impressions of Project 6-8, and how has the manner in which the playoffs are unfolding altered your way of viewing Masai Ujiri’s apparent strategy for building the Raptors’ roster?

Hollinger: Precious! The advanced stats still question him, but he made a ton of progress last season and has obvious routes to further improvement. The deal looks better than it did last summer, certainly.

As to the greater question of the Raptors season, it has to be considered a rousing success on most levels. Fred VanVleet made the All-Star team, Scottie Barnes won Rookie of the Year, and Pascal Siakm made All-NBA. The Raptors won 48 games and took Philly to six in the first round. Entering the season, anybody would have taken that.

Project 6-8, as you call it, seems to be where the league is headed, but the series against the Sixers also showed some of the limitations of that approach. Sometimes, having a real center is actually helpful.

The remaining bigger-picture question is whether this iteration of the Raptors has any real championship equity, and if so, what would need to happen to push them there.

Koreen: With all due respect to the taxpayer mid-level exception sweepstakes (which I think could be more interesting than usual), I want to focus on the two biggest decisions the Raptors have to make, which could occur in concert with their two best players — at least presently. Both Fred VanVleet and Pascal Siakam are extension eligible this offseason, although Siakam’s negotiating window doesn’t start until October.

Before we get into their specific situations, I’m wondering what you think about veteran extensions in general. Obviously, the longer a “bad” contract is, the worse it is for a team, and the longer a “good” contract is, the better it is for a team. Given the way deals for veterans have gone recently, do you think you would err on the side of getting a deal done or, ahem, “maintaining flexibility?”

Hollinger: In Toronto’s case, I would probably opt toward getting a deal done, particularly with VanVleet, who can opt out and become a free agent in 2023. This is because the Raptors are in what I call the “Bird rights trapzone, where a departing player in free agency cannot easily be replaced with another one, because they don’t have the cap space left to sign a comparable player. (Theoretically, Toronto could sign a big contract to replace VanVleet in 2023, but only if Gary Trent Jr. also walks and the Raptors make no other salary adds between now and then). Thus, retaining the players’ rights is almost always the way to go.

With Siakam, the argument is a little more muddied because of his age, higher initial contract, and the fact he’s already signed through 2024.

Koreen: For the reason you just laid out, VanVleet is the more interesting case for me. He is the cultural touchstone of the franchise and the natural heir apparent to Kyle Lowry, but also has shown signs of wearing down as seasons have progressed. Also, aside from the final nine games of the 2019 title run — pretty big games, John! – his playoff track record hasn’t been great.

He can either opt out of his player option for 2023-24 and sign a four-year extension, or opt in and sign for three more years after that. The first way would earn him a bit more money, but either way, he’s looking at a deal starting at about 20 percent of the cap. How do you view this from the Raptors’ perspective?

Hollinger: He’s 28 and just made the All-Star team. Players like that are expensive. While the Raptors have to be slightly leery of locking him in until his mid-30s, a rising cap should also remove some of the sting in the out years. In the big picture, if VanVleet becomes a free agent next summer, there’s a real chance another thirsty team offers him crazy money. Locking him in at an entirely reasonable $25 million-ish per year salary takes that possibility off the table. Toronto should be very willing to do this.

Koreen: Alternatively, if you’re VanVleet’s agent, what are you advising? And how much does the plethora of teams who could have upward of $25 million in cap room in 2023-24, at least as of now, play into things? We all know that VanVleet is fond of betting on himself.

Hollinger: Alas, this is why I think this will probably play out longer. Remember, VanVleet can always do an 11th-hour extension before free agency next year by opting into his contract in June and building an extension off that number. So from his perspective, the only reason to agree to a deal now is the security of landing the bag. As you point out, that bag could be significantly larger next summer even if he doesn’t have a particularly good year, just because of the supply-and-demand situation in the free-agent marketplace a year from now.

Koreen: Our pal Danny Leroux just wrote about the extend-or-trade scenarios that face various teams. How aggressively would you shop VanVleet around the league if the Raptors couldn’t come to an agreement with him? How do you see his trade value right now?

Hollinger: Kyle Lowry was the latest example of the Raptors getting some value from departing free agents. If the Raptors had some indications that Fred was going to walk after the year, then yes, I think it behooves them to shop around and determine his trade value. I think he could get two first-round picks from a team, or one plus a prospect, if they knew he would re-sign with them next summer.

That said, if the Raptors think he’s trying to get a larger bag but aren’t particularly worried about him as a flight risk, then they may be more comfortable playing this out. I think that is the more likely scenario. In that event, I think Toronto’s stance should be more along the lines of keeping their ears open without being particularly compelled to take action, unless somebody bowls them over with a crazy offer.


Pascal Siakam and Fred VanVleet. (Douglas P. DeFelice/Getty Images)

Koreen: To me, the Siakam case is less interesting. As of Oct. 1, the Raptors can offer Siakam a three-year extension worth up to nearly $129 million. Unlike VanVleet, Siakam has no player option for 2023-24. He’s coming off an awesome season, but that was on the heels of some poor, if explainable, play. We’ve seen how slow-playing potential extension talks can sour team-player relationships. Is there any merit in trying to get Siakam’s signature on an extension a bit below his maximum, or are you kicking these talks down the road?

Hollinger: Any extension with Siakam is going to start at $40 million a year and won’t kick in until his age-30 season, which makes it a fairly risky deal from Toronto’s perspective, even if a rising cap may shield them from the worst of it .

That said, I do think there is a bit of an argument for taking care of him right now, which is that you’d rather sign him to a five-year deal when he’s 28 than do the same thing when he’s 30. Siakam’s deal will remain tradeable even after he signs it, unless he starts a precipitous decline almost immediately.

My biggest argument against doing it is Scottie Barnes. He’ll be on a max deal (if not a supermax) starting in 2024-25, which means the Raptors have to think hard about who else they want to pay big money. It’s possible they decide that paying all of Siakam, VanVleet, Trent and OG Anunoby makes sense for them, but that is a very expensive quintet – and one that still has no centre. Historically, the Raptors will spend into the tax a bit for the right team, but they aren’t going to sign up for what the Clippers and Warriors are doing with six-figure tax bills.

As a result, I think flexibility becomes the go-to word here. Toronto still has two years to extend Siakam’s deal and would have the advantage even if he hit unrestricted free agency in 2024. I would play this out for another year before I committed if I were in the Raptors’ front office.

Koreen: With so few “sexy” teams having cap room this summer, and so many of the best free agents being so polarizing, I have a feeling the non-taxpayer mid-level exception could be a more meaningful spending tool than usual this offseason, especially for teams looking to compete. A few questions:

  1. Do you think Chris Boucher or Thaddeus Young will command the full MLE?
  2. Do you have favorite targets who could be in that range?
  3. If you were the Raptors, and have to factor in potential extensions/raises for some or all of VanVleet, Siakam, Trent, Anunoby and Achiuwa in the next few offseasons, how reticent would you be to give out multiple years in such a deal to any free agent – ​​whether your own or from outside the organization?

Hollinger: Let’s tackle these one by one.

For starters, I think Boucher is more likely to have interest at that price point than Young just because of the age difference, especially on a multi-year deal. The Raptors are far enough below the tax line that they could theoretically sign both to MLE-sized deals using their limited Bird Rights and still have enough to use their own MLE, so they’re in a good spot to retain each. Certainly, I don’t see either getting more than the MLE.

I’m going to jump to No. 3 straight away, because the biggest issue for Toronto on Boucher and/or Young won’t be money but years. How far out do they want to commit another $7-10 million for each of them when their salary situation gets trickier two and three years down the road. They have to think through some of the redundancy in having both as well; don’t they want a real center at some point? I could easily see the Raptors signing both for more initial money than expected, but with a lightly guaranteed second year to maximize flexibility and their ability to put either in a trade for another player.

As for No. 2, I think it’s obvious that Toronto needs another real guard on the roster, which would also help them avoid running VanVleet into the ground. Ricky Rubio and Tyus Jones are aspirational targets, but I don’t think either is coming here on the mid-level to be a backup. More realistically, old friend Delon Wright would be a nice fit here and could likely be had for less than the MLE. They also might take a long look at Eric Bledsoewho is almost certain to be waived by Portland.


Arizona’s Dalen Terry. (Brian Rothmuller/Icon Sportswire via Getty Images)

Koreen: Finally, you were at the draft combine. The Raptors pick 33rd. Any guys beyond the top 20 or so that piqued your interest?

Hollinger: Yes, a few. I really like Arizona’s Dalen Terry and think he’d be a perfect fit for Project 6-8, but he might be long gone by the time the Raptors pick. More realistically, I’m a fan of Duke’s Wendell Moore and think he’d give the Raptors a solid option at backup 2

A couple of guys who might fit under the banner of “Project 6-8” are Colorado State’s David Roddy (6-5 but built like an offensive lineman), Wake Forest’s Jake LaRavia and Marquette’s Justin Lewis. I have a first-round grade on LaRavia and his stock appears to be rising, so that one might be more wishful thinking.

Finally, the Raptors love their internationals and still could use some help in the middle, so I would keep an eye on French big man Ismael Kamagate, a raw rim-runner who could end up being a stash pick they wait to bring over until 2023 .

(Top photo of Fred VanVleet and Pascal Siakam: Cole Burston / Getty Images Sport)

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