The anniversary of “The Shot” gives and takes away. On May 12, 2019, Kawhi Leonard delivered the first Game 7 walk-off in NBA history, a crucial moment in the Toronto Raptors’ quest to secure their first NBA championship. One year later, remembrance of Leonard’s four-bounce miracle is fun, sure.
It also casts to the forefront of our consciousness the reality that the Raptors are not presently engaged with the Boston Celtics (or the Indiana Pacers, or a Philadelphia 76ers rematch) as they attempt to defend their title. Under normal circumstances, the Eastern Conference Finals would be taking place this week, set to begin as early as Sunday. The Raptors, one of the season’s best stories, are instead in the same holding pattern as everyone else, with a narrative more richly hanging in the balance than most.
That leaves some big questions unanswered for whenever the NBA resumes. To help us answer some of those questions as best as possible in the present, we’ve tagged in former Memphis Grizzlies vice president of basketball operations John Hollinger for a wide-ranging chat about the state of the Raptors. Hollinger, now a national NBA writer for The Athletic, shared his thoughts on Fred VanVleet’s next contract, the Raptors’ young core, how Pascal Siakam stacks up with another young Atlantic Division star, and more.
For more Hollinger on the Raptors, check out his recent appearance on the Raptors Reasonablists podcast.
Murphy: The 2019-20 and 2020-21 seasons initially looked like transition years of sorts for the Raptors. They would run it back, so to speak, keep an eye out for potential trades for their veterans, gradually shift more responsibility to their young players, and keep their cap sheet as clean as possible for summer 2021. That, in theory, was the next genuine competitive window.
At least in the regular season, the Raptors changed that thinking. Kyle Lowry continued to defy the age curve, Marc Gasol and Serge Ibaka stuck around and continued to produce, and Pascal Siakam showed growth in a trial run as a No. 1 option. While recognizing that there are a lot of unknowns about what the salary cap will look like for 2020 and 2021, do you think the Raptors’ success this year has — and should — shift the thinking about their window for contention? Are they close enough to operate with a win-now mentality instead of prioritizing flexibility for a later date, or is that too difficult to conclude without seeing how the team performs in the postseason? Is the Giannis Antetokounmpo scenario planning worthwhile?
Hollinger: Fortunately, it seems the Raptors will get a crucial window into the potential returns on this strategy after the season. If Antetokounmpo signs a five-year extension with the Bucks after the season, that removes the biggest reason to stay flexible for 2021 free agency. Other prominent players will become free agents, but none has the ability to swing a franchise’s fortunes the way Antetokounmpo can.
As far as next season, the win-now mentality and summer 2021 could be headed for a collision. VanVleet, Gasol and Ibaka will all be unrestricted free agents; some other players who played important, but lesser roles (Chris Boucher, Rondae Hollis-Jefferson), will be free as well. And OG Anunoby will be eligible for a contract extension.
Committing to that group for terms beyond next season would crowd out all the cap flexibility in 2021 and basically tether the Raptors to those players for the near future. Given the ages involved (Gasol is 35, Lowry is 34 and Ibaka is 30), they’re likely buying into a declining asset. And as good as the Raptors were this season, I think it’s still fair to ask if they were a serious contender against the likes of Milwaukee or even Boston.
What the Raptors have done really well these past few years is walk the middle ground, and they may have an opportunity to do it again. Signing at least one of Gasol and Ibaka to a one-year deal, even if it’s an overpay, solves the center spot while keeping the door open to the future. If you assume Norman Powell will opt out of his final season in 2021-22 at $11.5 million (he could nearly double that in free agency if his level of play holds steady), then the Raptors could re-sign VanVleet, as long as the number stays below about $20 million, and still have room to max out Antetokounmpo.
It would be tight — they’d need to fill out the rest of the roster on one-year deals using exception money, the luxury tax tap dance would be a factor all year and they’d risk leaving themselves high and dry if no big free agents came while Lowry, Powell and their starting center all left.
But it’s important to remember how these situations have played out for other teams, most recently with Anthony Davis. The odds of Antetokounmpo (or another high-wattage star) actually becoming an unrestricted free agent are low. More likely than not, any scenario where he leaves Milwaukee happens via trade due to the threat of his leaving for nothing in 2021. So, the Raptors may not have to play this all the way out to the following summer — just maintaining the flexibility to threaten to sign Antetokounmpo is likely enough. Having players on one-year deals assures they have the matching salaries to execute a trade for him if and when that time comes.
Murphy: That well-established pivot foot has been a defining feature of this era. The Raptors are going one way, but the ability to turn in a different direction (at first blowing it up, then going all-in) has always been maintained. I think that’s a pretty clear organizational edict, and just about the only thing Bobby Webster has ever tipped his hand about publicly is the premium the team puts on flexibility.
So I’m in agreement with you on a lot of that, particularly with respect to the centres. My colleague Eric Koreen and I agree on a slight preference toward retaining Gasol, in part due to his perceived openness to a one-year deal. Our readers disagree, but a multi-year deal for either seems counter to the big picture.
VanVleet is the biggest question, as his next contract will likely be the biggest swing factor in Toronto’s 2021 flexibility. As you noted, with Powell looking like a potential opt-out, Siakam’s max contract extension and a few cap holds are all the Raptors have on their books right now. If the Raptors insist on maintaining a max cap slot for 2021, there could be a loose theoretical limit on their willingness to pay VanVleet this summer.
How do you see the market for VanVleet shaping up? There aren’t many teams with ample cap room, but there are a couple that could certainly use a 26-year-old point guard with upside and leadership qualities. If you’re the Raptors, would you balk beyond a certain price point? What about if you’re the Pistons or Knicks, considering VanVleet is quite good but hovers a bit below league average in true shooting, and struggles to finish?
Hollinger: VanVleet is definitely a potential fly in the ointment. As I mentioned earlier, I think above $20 million, it gets really hard to wedge in a max cap-room slot. Additionally, I don’t think VanVleet offers surplus value at a number that large. He’s a good, tough, player, but he’s not a top-10 point guard and is unlikely to ever become one. He turns 27 next year, so he is probably what you’re getting.
Unfortunately, I think the Pistons and Knicks are real threats to upset Toronto’s apple cart by making an offer the Raptors would be reluctant to match. The Knicks and Pistons will have max cap space and have a glaring need at point guard. The Pistons employ VanVleet’s former coach in Dwane Casey, while the Knicks fawn over anything that Masai Ujiri has touched, even if it’s Andrea Bargnani. The Raptors have to be praying both teams end up landing one of the elite playmaking guards in the draft and decide to direct their cap room to other positions.
Of course, VanVleet has agency in that, too. Would he take less money to stay in Toronto? History says the answer is usually no, so he’d be an exception.
Murphy: Not only is there not much of a history of discounts like that, VanVleet strikes a figure as someone who is keenly aware of his value and his points of leverage. He’s smart and will surely know the situations in Detroit or New York. He said recently he may be more open in the current climate to a short-term deal, but that doesn’t help Toronto’s big picture any. Less term might require a higher annual value, and a one-year deal would only serve to inflate VanVleet’s cap hold and expand the number of suitors with cap space.
If VanVleet walks, scenarios can get murky quickly. For one, the Raptors’ ability to remain at the higher levels of competition in 2020-21 could be compromised. He would also represent one less core piece alongside Siakam, Anunoby and Terence Davis with which to coax a free agent. It’s not as if the upcoming free-agent class (or the Raptors’ cap sheet, particularly if they retain one of Gasol or Ibaka) will allow them to replace him.
Is it considered illegal cap circumvention if part of VanVleet’s deal includes selling his branded merchandise at Scotiabank Arena? (I’m only half-kidding.)
I want to pivot to discuss those younger core pieces, and particularly your faith in the Raptors’ continuing ability to find them.
We’ve also been high on Davis since the start. I would wage wars in Anunoby’s name. Our colleague Sam Vecenie ranked the Raptors’ crop of young players the seventh-best in the league earlier this year, but Siakam is going to graduate from that group on his max extension next season. Intriguing names like Boucher — a player we are pretty high on — and Oshae Brissett are restricted free agents.
The Raptors finally own their own picks for a change, but even for them, late firsts and seconds are uncertain assets. How confident are you in Toronto’s ability to maintain a successful back half of the roster on the cheap as its veterans move on and/or its young players graduate to higher pay tiers?
Hollinger: To answer your first question, it is absolutely cap circumvention to do stuff like that and the league is very much alert to potential abuses of it.
More broadly, the VanVleet situation affects so many variables for the offseason. If he goes, Davis can soak up some of those minutes, but would they need to use their full midlevel on another guard? And if so, would they aim older (i.e., to compete in 2020-21) or younger (to pair with Antetokounmpo or another white knight who would ride in for 2021-22)?
Regarding the back half of the roster, I think the Raptors have proven over and over again that they can find decent players on cheap-ish deals. Every once in awhile, they’ll bring in a Stanley Johnson just to prove they’re human, but Toronto’s batting average on inexpensive free agents and developmental players has been vastly superior to its peers.
That said, outcomes like the Raptors have had the past few years still might not be attainable on the regular. There’s a chance element to that, too. VanVleet and Davis have been better than a lot of the guys they picked in the draft; the odds are exceedingly unlikely they can come up with two undrafted players like them in a five-year span again. They will be drafting in the 20s in a weak draft this year, so the odds of a player like Siakam or even Anunoby are not great.
The good news is they don’t need to crush home runs at this point. Just getting Hollis-Jefferson and Boucher out of their low-salary spots will help a ton because the top of the roster remains very strong even without Leonard. The Raptors’ front office has repeatedly shown the ability to pull that off, so you should have as much confidence in them as any group in the league.
Murphy: I’m not sure it’s a fair assumption Davis would absorb VanVleet’s minutes with one year still on Patrick McCaw’s deal.
I’m glad your confidence remains high. I know it’s difficult to separate talent identification and player development and chance, especially since everything in basketball (as in life) is a small sample, but they are a big part of the front office and cultural identity the Raptors have been building. I think they operate with faith their track record will continue, to the extent of being able to attract and develop capable bench players, if not find another Siakam, VanVleet or Anunoby.
Speaking of Anunoby, he is extension eligible this summer. Given his smaller cap hold and the Raptors’ preferred 2021 flexibility, does it seem like a pretty clear scenario in which it makes sense to let him hit restricted free agency with an acknowledgment he’ll be taken care of once the flexibility is leveraged? How difficult is it to navigate situations like this from the front-office perspective, where the logic is clear and understood but the goals of player and team are momentarily misaligned?
It tends to be the cap-strategy wrinkle I have the hardest time selling people on, so I’m hoping for an assist.
Hollinger: I feel like you’re intentionally tempting me but … McCaw isn’t good. I have no idea why he was playing so much. He may theoretically become good (length, quick hands, and once upon a time he would actually shoot) but is nowhere close at the moment and doesn’t seem to be getting any closer. Statistically, he is easily the least effective of the Raptors’ regulars regardless of your chosen metric and had by far the worst on-off numbers of the cast. I’ve started to suspect he owns compromising photographs of important Canadians.
OK, let me gather myself before I write a page and a half about this. Anunoby, obviously, is far more crucial to the Raptors’ long-term hopes.
Here is the deal: His cap hold for summer 2021 is $11.3 million and that is extremely important. The Raptors can let that number sit on their cap while they deal with the A-list free agent of their choice, and once that is done, they can sign Anunoby at a larger number.
Cap-wise, the only advantage from the Raptors’ side would come if he were willing to sign for less than his cap hold, which seems exceedingly unlikely. Instead, Toronto’s likely position is to leave that number on its books and risk having to match a large offer sheet on Anunoby.
I see two scenarios in which an extension makes sense. The obvious one is if the Raptors don’t re-sign VanVleet. In that case, they would likely have enough runway in 2021 to extend Anunoby’s contract at a number more in line with his market value (probably in the $17-22 million a year range) and still retain more than enough cap room to make a run at a max free agent.