End-of-Season Mailbag Part 2: Raptors’ offseason scenarios

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Photo credit: Trung Ho / TrungHo.ca

I suppose the end of the season calls for a lengthy mailbag. There’s no sense doing anything but getting right to it, so let us do just that. Part 1 dropped yesterday and focused primarily on coaching questionsYou can find all of the previous editions of the mailbag here. You can ask me questions at any time using #RRMailbag Twitter, and I’ll be sure to include them in the next mailbag, no matter how long between (unfortunately, it’s too much to keep track of Qs from the comments, so Twitter/email is preferred).

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Alright, let’s do this.

As noted, Part 1 of the mailbag focused on the team’s coaching search, ending off on the note that the Raptors absolutely need to make more changes than just on the bench. In addition to this mailbag, I wrote at The Athletic about what each Raptor should focus on this summer and wrote about OG Anunoby’s bright future for Dime Magazine at Uproxx.

Summer Roster Changes

I don’t think it does, at all. Whether the Celtics won or lost wouldn’t change the fact that the Raptors dramatically underperformed against the Cavaliers, and when you’re building your team, you can really only focus on being the best version of yourself regardless of what everyone else is doing (except in the case where you’re deciding when the right time is to blow things up; the Raptors aren’t built to do so until next summer). The Celtics doing well certainly makes the Raptors’ loss feel worse and magnifies just how vulnerable the Cavaliers actually were, but the nuance there – Boston having far fewer bad (and small) defenders, the Cavaliers shooting significantly better on open shots against Toronto, the mental hurdle for the Raptors – is such that you should have come to roughly the same conclusions about the Raptors regardless of whether Boston sweeps Cleveland, had gotten swept, or anywhere in between.

I would fire Blake Murphy as general manager of the Toronto Raptors, but only after giving Lucas Nogueira a four-year deal.

From Devang D: Is trading DeMar really an option and if so what type of return are we looking at?

I’m going to write a full column about this at some point because the idea of moving DeMar DeRozan requires a lot of nuance. The devil and god are raging inside me with this idea, given how fond I am of DeRozan and also what some colder analysis would say about the team’s bottleneck. I need more time and words with it. But briefly…

It’s going to be tough. On several fronts. It’s going to be tough to get fair value for him, first of all, given how few teams have the requisite cap flexibility to take him on without sending out bad salary. It’s going to be tough to sell the fanbase on dealing the face of the franchise and one of the only stars who chose to stay, too. Loyalty on both sides is a little overstated in sports, but DeRozan has absolutely embodied that, and for a franchise that’s lacked it for so long and has a fanbase that largely reveres DeRozan,  one of the three best Raptors ever, it’ll be difficult to move on from him. That’s not sound reasoning in isolation for making or not making moves, and so we come to it also being tough to imagine any DeRozan trade getting the Raptors over the hump, anyway. If they admit that just reaching the finals is their championship, then sure, but a DeRozan trade isn’t likely to make them legitimate contenders.

Understanding all of that, a DeRozan trade would probably have to satisfy one of three criteria:

  • Provide significant financial relief not just to help clear the books for 2020 but to give the team more flexibility the next two years. This likely means getting back a slightly lesser player on a smaller contract.
  • Return an asset that can help now while also continuing to build for the Raptors transitional era in 2019 or 2020. Whether that’s a young player still establishing himself or strong pick equity is a matter of market (I’d think a young player is easier to come by than a top pick in this draft), and this would likely require the Raptors to take real salary back to sweeten things and make the math work. This is probably the return I’m most skeptical about being available on the market – if a team is going to dangle a top-five pick in a strong draft, they’re going to have a lot of offers, and DeRozan (with his contract) might not be enough without taking on some bad salary in return. It’s also the least certain of the scenarios to see the Raptors improve or sustain next year, given the volatility of rookies (and the limited likelihood they’d open up significant financial flexibility in such a deal).
  • Make the Raptors the favorite to come out of the East. This is almost impossible given where Boston and Philadelphia and wherever LeBron James ends up are heading, but if you’re going to trade one of the all-time faces of your franchise, it better take you to another level now or help get you there in the future.

Satisfying even one of those criteria could be difficult, and you’d also need to make sure DeRozan is fine with the landing place and it’s not a bad situation. You can trade a player of that stature who has carried himself like he has, but you still have to at least try to do right by him if you’re both moving on. A DeRozan trade, then, is fun (if painful) to think about, but in my eyes seems unlikely to be “worth it” in the end given the team’s ceiling regardless and how much he’s meant to the franchise.

In terms of specific deals, I’ll probably save that for another offseason mailbag that’s focused solely on trade proposals. Denver is an interesting trade partner for either Raptors star, though.

I’ll address this one specifically because I’ve seen a lot of it in the last week or two. I still have faith in Andrew Wiggins. I think it’s much too early to give up on him improving as a playmaker, a shooter, or a defender. But that contract was a terribly unnecessary gamble that has the potential to be an albatross not so far in the future, and Wiggins has yet to show he’s a consistent impact player at either end of the floor. Even if you think Wiggins has a lot of upside he’ll eventually tap into (I do) and have faith in the Raptors’ player development staff (I do), you’re still betting on an awful lot to break right just for Wiggins to reach DeRozan’s level, on a worse contract. I get the idea – established star for potential star, potentially extending Toronto’s window, the passport, etc – but if you’re the Raptors, you need to get more back in that deal, likely in serious pick equity. Again, love Wiggins, that contract just has the potential to be a disaster.

I wouldn’t use the word prefer, as they are all my sweet, good sons, and I want none of them to go anywhere. In terms of how willing I’d be to part with either, though, I would probably put C.J. Miles first (he’s a great shooter and a great dude but is also the only member who could provide salary relief or bring any salary back), then Jakob Poeltl, Delon Wright, Pascal Siakam, and OG Anunoby. (Fred VanVleet is a free agent so I’m leaving him out.) I wouldn’t quibble with flipping Poeltl and Wright or even if some were less high on Siakam, but I think the upside is highest with Anunoby and second-highest with Siakam, and so maintaining them into the next era (or at least seeing what they become by then) makes a lot of sense.

This is a good test. So basically, Myles is asking which Raptors you could trade for the draft rights to Tomislav Zubcic or an equivalent. That is, what players could the Raptors unload without attaching a pick or prospect to entice a team to take them on. (For recent context: The Raptors sent out Cory Joseph with nothing but had to attach a first-round pick and a second-round pick to DeMarre Carroll.)

I actually think Serge Ibaka is the only player who definitely fails the test. There’s no way anybody is taking the two years and $45 million left on his deal without a sweetener at this point, unless it’s part of a much bigger package. Norman Powell would probably be the next closest, but the fact that he only counts at his minuscule 2017-18 salary up until July 1 opens a window for tight-capped teams to take him on without worrying about salary matching for the time being.

The next group is dependent a lot on the market this summer. Jonas Valanciunas, for example, is much more attractive to teams now than he would have been a year ago (with his improvement and another year off his deal), but $16.5 million is still a lot in an offseason where so few teams have flexibility. And the two stars would find homes “for free” in general terms, but the Raptors would have to take salaries back to make the math work (which works as a de facto sweetener, whether intended or not). C.J. Miles, even a year older, probably passes the test with an $8.3 million salary, and the rest of the roster is entry-level contracts the team could come off of quickly (except maybe Malachi Richardson, who earns close enough to the minimum for that not to matter a ton).

This might depend at least in part on who winds up as the team’s head coach. That’s not to say that they’ll have a dramatic say, but the type of system or general type of tactician they are could make certain players better or worse fits. Jerry Stackhouse, for example, would probably push to keep Norman Powell, while Nick NUrse (or even Mike Budenholzer) might have use for Lucas Nogueira. Ignoring that context, I think Powell and Nogueira are gone but Fred VanVleet is back. I don’t have a good sense, otherwise – the team will probably be aggressive in shopping everyone to see what might work, and it’s a little too early to know what the market might allow for. I’d guess it’s likelier DeRozan goes than Lowry and I’d guess that Ibaka proves unmovable within reason.

The article referenced where I break down Fred VanVleet’s restricted free agency can be found here. To summarize briefly, VanVleet is restricted and is subject to the Gilbert Arenas provision, so his salary is capped at the full mid-level exception for his first two seasons. The Raptors can go as high as four years and $36.9 million using their Early Bird Rights on him, and another team could go as high as four years and an estimated (and back-loaded) $74.4 million that the Raptors could swallow hard and match. As far as the playoffs, I actually think if anything, they highlighted the importance of a healthy VanVleet to what the Raptors were this year, so unless there’s residual concern about his shoulder, I think the bag is just as secure.

One thing working in the Raptors’ favor here is that it doesn’t seem likely there’s an out-of-control market for VanVleet. He’s good, and teams would be smart to target him, but non-max restricted free agents sometime struggle to land good deals early in the process and very few teams project to have meaningful cap space this summer (exceptions will come into play here). I think if you’re VanVleet’s camp, you’re hoping for four years at the full mid-level (an estimated starting salary of about $8.6 million), and if you’re the Raptors you’re obviously hoping he comes in cheaper than that (maybe something like four years and $24 million). If the market is cold, it’s possible VanVleet is amenable to a two-year deal that bridges to his unrestricted free agency in 2020, when his salary would be uncapped, the rest of Toronto’s big deals expire, and more teams figure to have cap space.

For Raptors planning purposes, it’s probably best to assume a VanVleet salary in the $6-8.6 million range for next year.

General Raptors

DeRozan’s defense improving would be a lot more meaningful in the big picture, particularly in the playoffs. Despite all of his incremental (and often remarkable) improvements, DeRozan still grades out as a major negative on the defensive end, and despite occasional flashes, teams still look to attack him with regularity. It wasn’t Toronto’s offense that fell off in the playoffs this year, and having multiple attackable defenders on the floor was a big part of why Cleveland was able to hang points on them at will. Anunoby’s offense improving would be a lot of fun and continue to make the Raptors’ attack more dynamic, but Anunoby’s role is somewhat capped by the presence of the two star guards, anyway, and he was already fairly efficient with the opportunities he received.

Both are important, and Anunoby’s offense will dictate whether his ceiling is elite 3-and-D player or potential All-Star. DeRozan’s defense would be a higher-leverage improvement given the team’s makeup and how they’ve performed in recent postseasons. And he has it within him.

I would prefer DeRozan to become even a league-average defender, even if the effort to do so meant his offensive workload had to come down some (which might not be terrible for the team as a whole as they continue to try to become more versatile). A 40-percent 3-point shot would be awesome – the Cavaliers straight-up ignored DeRozan when he didn’t have the ball, and that puts undue pressure on the team’s other ball-handlers to operate within tight space – but again, the offense was less of an issue than the team’s defense. Points are points, of course, so either would be a wonderfully welcome addition, I just think the Raptors are better equipped to succeed offensively with the current version of DeRozan than they are defensively.

I’m not sure it really matters, because he seems to have a pretty keen understanding of his role right now. I think it’s pretty clear he’s more advanced on the defensive end than on the offensive end, though he impressed on both sides, if that helps at all. Offensively, his first instinct is probably to score given the small windows he has to operate within, but he was well ahead of expectations in terms of reading the defense, delivering dump-off passes, and so on. He’s also flashing pretty good instincts cutting without the ball. He reads and anticipates at both ends pretty well, which should be a good harbinger of development to come.

In terms of becoming a primary scorer, we still need to see a lot more before that kind of projectability comes into focus. Right now he profiles as a 3-and-D piece with some nascent playmaking and shot-creation. It’s not at all difficult to imagine that expanding with his first real NBA offseason – look at the strides Pascal Siakam made as a creator and perimeter player last summer and apply even half of that to Anunoby, and he’ll be a multi-faceted weapon much earlier than expected. Still, exciting though Anunoby is, it’s probably best to keep expectations reasonable (read: maximizing the skills he’s flashed rather than dreaming on new ones) until he shows those new skills a bit more regularly. Give me more of Anunoby creating for himself and others in the regular season to build those skills up, though, even if it comes at a short-term cost.

I wrote more about OG Anunoby’s bright future for Dime Magazine at Uproxx yesterday.

Basketball IQ, or situation reading and reacting if you prefer, is probably the hardest thing to improve upon without actual game reps. You can only watch so much film, and summer pick-up runs are only so helpful. Real-time runs are important in this regard. But experience goes a long way, and there’s a reason most players develop along a curve rather than entering the league as finished products. The speed and physicality of the game is tough to adjust to, and it’s with the benefit of a rookie season or first playoff series or general failings that players can regroup and try to improve. This is standard cliche stuff, but that’s all you can really use when talking about some pretty intangible skill development.

Norman Powell is an interesting case in this regard, because he’s actually a really intelligent basketball person and still seems like he reads offensive situations poorly at times. He’s had a fair amount of NBA experience to this point (over 3,000 minutes), but it’s possible that because his role has changed so frequently that the experience hasn’t taken, because the experience is split into different buckets of experience. I’m not sure. Maybe I’m trying to give leash to a player I still think is going to be fine in the long-run. It was weird to see Powell regress as he did this year, and I don’t have a great explanation for it.


I’m not willing to consider a future in which we don’t have VanVleet’s waves. Nobody on the roster has that tool in their repertoire. Cory Joseph ain’t walking back through that door.

The Toronto Raptors, obviously.

(Probably the Magic. The Hawks have less on pure talent to surround James with, even with a top-three pick coming their way, but they also have enough potential cap space to add a significant second piece alongside him, whereas the Magic are in a tough spot for cap space and immediate pick equity.)

Meeks just had a really good showing at the G League Mini Camp in Chicago, and here’s hoping that continues building the momentum a really strong rookie G League season saw him get going. In terms of his NBA future, it’s clear his rebounding is an elite skill that should translate even without the requisite bounciness (the G League is full of springy rebounders, and Meeks out-rebounder most of them), and he’s a decent enough playmaker that his lack of shooting range isn’t a huge deal. He also raised his ceiling from “certain defensive minus” at the next level to “potentially passable,” to the point where I’d be comfortable having him compete for the third center slot likely to be abandoned by Nogueira (sigh). The more likely scenario, though, is that Meeks lands in Summer League with another team and gets a camp invite from there, because G Leaguers don’t often stay in the same system long.



Poor Serge. Everyone but Marwan has turned on him. (People need to drop the age jokes at this point, by the way.)

Ibaka definitely had a tough playoffs, but there’s reason enough to think he can maintain the regular season version of himself. That’s not what the Raptors paid for – it always looked like a modest overpay and now looks even worse – and it would be helpful if whoever the new coach was didn’t think of Ibaka as the team’s third piece and instead thought of him as just another guy in the rotation. That’s tough with salary and role expectations, but Ibaka isn’t a third-star type, struggled with the new offensive scheme, and waving all of that away with the usual calls to move him to center ignores that he probably wouldn’t be much better off there overall.

He’s a fine rotation piece, nothing more at this point, and he’s overpaid enough that people should probably get used to that, since his contract would be pretty tough to move. I think Jonas Valanciunas has more value given his slightly better contract and elite rebounding and pick-and-roll work, and it was at least good to see that they can coexist successfully over a large sample considering the team might be locked into both a while longer.


I wish I had a clear answer on this one, but Canada Basketball has been quiet (as they have to be) with their intentions in terms of balancing NBA talent with talent who will be available for the later qualifying games. My guess is that they’d like to have at least some of the NBA players who might suit up in a hypothetical World Cup or Olympics appearance. Once we eliminate players who are free agents, coming off of injury, or in the draft, we have a list that could include Cory Joseph, Tristan Thompson, Kelly Olynyk, Jamal Murray, Dillon Brooks, and Trey Lyles, plus maybe fringe names who would be willing to get two games in ahead of Summer League like Naz Long, Khem Birch, and Xavier Rathan-Mayes. Nik Stauskas and Tyler Ennis loom, too, depending on how their offseasons starts.

I’m discounting Chris Boucher, who will probably be on a strict offseason plan as he works back to 100 percent, and Andrew Wiggins, who I’m in believe-it-when-I-see-it territory with. And then you have all the European pieces (most notably the Scrubbs, my personal favorite Melvin Ejim, and Brady Heslip) and G Leaguers (Anthony Bennett, Aaron Best, Kaza Keane) who helped Canada go 3-1 during the NBA season. Yes, it feels like I just listed a ton of players, because Canada’s pool is the deepest it’s ever been. And hey, why not get R.J. Barrett some more international experience?

So, yeah, the team for those two games could be pretty loaded. As always, especially with low-leverage games, players may opt to sit out and focus on their development or free agency or recovery or Summer League or whatever, and Canada Basketball might want to have a mix of high-end talent and talent that will be available in September. That the two games are on home soil could go some way toward locking up commitments. It should be a lot of fun.

Reynolds is coming off such a shaky rec league season – on the heels of a bad 2017 RR tournament – that I’m not sure he even warrants space here. I think the biggest move will probably be you and I connecting and finding a point guard to round things out. Super Teams are about to kill the RR tournament. In terms of the worst, theScore’s team can never seem to get out of its own way. A bold prediction: Multiple teams names themselves “___ and the Three __,” to the point where I have to email people to be more original to avoid confusion.

So that we can learn to pick ourselves up. And because LeBron James fights with his heart, his brain, and most importantly, his underlying hatred of the Toronto Raptors.

I’m definitely single, I’ll tell you that much.

Sir. I am a professional. I won’t answer immature questions about things such as this. There are real, mature, adult questions to answer about serious matters….

I’ll start with the stars, because I have no idea what to think of the outcome. I’d take the over on 5.75 stars. The three previous encounters between Kenny Omega and Kazuchika Okada earned 6, 6.25, and 6 stars respectively, ranking as three of the top-four rated matches of all time by Dave Meltzer. (I actually thought the second meeting was the worst of the three, ranking them 1-3-2, but who am I to disagree with Meltz?) Given that lofty bar they’ve set, how loose Meltzer has gotten with the stars of late (Okada and Hiroshi Tanahashi the other week was great but hardly worth breaking the five-star scale for, in my opinion), and how layered the storytelling could be in a best-two-of-three match with no time limit (especially given all of the call-backs they used as they went along in the earlier three matches), I’m not sure how this one doesn’t at least touch the other installments. I’m very excited, and already have an early morning viewing party and breakfast planned to enjoy it love.

As far as a winner, I’ll go with Omega against my gut. If he doesn’t win it here, I’m not sure when he ever overcomes Okada, and if Okada wins, he’s pretty much out of compelling challengers (and he’s already mostly run out of records to set). Then again, I am a mark and am probably working myself into a shoot hoping my close personal friend becomes the champion.

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