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Draft Day Mailbag: How to move in, who to move out, and more

Let’s work through some scenarios.

There is probably not a need for another mailbag right now. We just did a two-part end-of-season mailbag (here and here) back in mid-May, and aside from now knowing Nick Nurse will be the team’s head coach for 2018-19, not a lot has changed. Same big questions, same vague answers, same sense of impatience and existential dread (non-basketball related). But it’s draft day, so why not re-focus a bit, right?

You 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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Let us.

Raptors at the draft

I think this is the first mailbag in the last five that doesn’t have a Kawhi Leonard question, to be honest. Which I totally understand – even if a trade for an extra superstar seems incredibly unlikely, you still want to figure out the best package you’d be willing to offer and how it measures up. The chances of landing both an elite player and a lottery pick are exponentially low – and might be counterintuitive since it would probably require sending out both Kyle Lowry and DeMar DeRozan to accomplish – but hey, throw a third and a fourth team in there and see what sticks. (There is actually a three-team deal that would land Leonard in Toronto that I could squint and see being close-ish, but salary matching is more difficult now that Rudy Gay has opted out, and it was always an incredible long shot.)

And hey, if people weren’t going to fire off trade ideas for a Devil’s Advocate/Reality Barometer, what purpose would I serve this time of year and in February? None. I am purposeless. So let’s hear ’em.

There seems to be some real disagreement on this one in asking around. Personally, I see a 25-year-old wing who’s shown to be a solid defender and who possesses the ability to create his own shot, and who has at least flashed an ability to knock down catch-and-shoot corner threes, and think he should have value. The four-year, $42-million extension that kicks in July 1 is now an overpay, but young, two-way wings with controllability rarely go out of style, and it’s not as if Powell would need that much of a course correction for the $9.6 million he’ll make in 2018-19 to be back within a reasonable salary for him. Despite what the advanced numbers showed this year – and they showed him being among the worst rotation players in basketball – I still believe Powell is an NBA rotation player with upside if the 3-point shot comes back.

Working in Toronto’s favor is that Powell only counts for $1.5 million for salary matching until July 1, meaning they could unload him to a number of suitors without having to take much on. If the Raptors were purely motivated to get off of his contract, an enterprising team facing a summer in which they don’t have meaningful cap space might be able to poach him for pennies on the dollar, simply eating the contract and sending back a second-round pick or the draft rights to Johnny Jabronie or whatever. That would give the team Powell at a low asset cost and preserve their mid-level exception. What’s more, if teams wait until July 6, they might be able to attach a contract in a deal for Powell (when he counts for $9.6 million), which would have the effect of lessening the fiscal impact of trading Powell for Toronto but also numbing the cost of a team taking on his deal.

With all of that considered, I’m confident the Raptors could find a home for Powell. The unfortunate reality, though, is that Powell is a distressed asset and the league knows the Raptors have a tax crunch, limiting their leverage. It seems unlikely you’ll get a major asset back for him, and in that sense, his “trade value” is fairly low.

The collective bargaining agreement requires that in a trade, every team involved sends something out and receives something back. That doesn’t have to just be players, though – teams can trade picks, the draft rights to players, or cash to satisfy this condition. So an NBA team is able to just send cash considerations in a trade. Each cap year, the CBA dictates a total amount teams can send and receive in aggregate, and this year that amount if $5.1 million. The Raptors are yet to use any of it, so they’re able to send out up to $5.1 million in trades between now and July 1. All it requires is another team being willing to accept cash for one of their draft picks, which happens a couple of times every season (and even more if a future second is included in a deal).

I think they’re trying. For an organization with deep pockets like MLSE, an expiring $5.1-million cash allotment is a pretty big asset. It’s still real money and likely comes from a bigger-picture budget the Raptors are operating with that includes future luxury tax payments (here’s an area where the Raptors skirting the tax for 2017-18 and receiving a tax disbursement from the tax-paying teams has real consequences), and so it has to be balanced against spending elsewhere for the coming year. Still, it’s a meaningful asset.

Here’s what I wrote about the analysis of buying a pick last week:

For the Raptors, it becomes a matter of figuring out the surplus value they can get from that pick…In a draft that projects as quite flat once it gets to the deep 20s and extends well past the second-round cut-off, it also seems likely the Raptors could wait to play the undrafted free agent market and still get players they like. In a strictly analytical sense, then, their willingness to pay for a pick should be the additional surplus value they think the pick would return over the top undrafted free agent, accounting for things like projected salary and contract type (two-way, two-years a la Fred VanVleet, using part of the taxpayer mid-level exception to tack on a third year a la Norman Powell, etc.) and the projected value of that player’s restricted free agent rights at the end of the deal. In less analytical terms, the Raptors simply have to decide whether real cash dollars that they won’t get to use again is worth the difference between second-round guy and undrafted guy, assuming second-round guy even gets drafted, which is hard to peg down this year.

In other words, they’ll likely try, but they’ll hit a point in negotiations where they’d probably be better off just grabbing the best undrafted player and earmarking that money in the budget for tax payments or use of the 2018-19 cash allotment that resets July 1.

Those seem like reasonable enough targets, for sure. To be honest, though, we don’t really have a sense of who the Raptors are interested in. They brought in so few names because they don’t have any picks, and while they might tell us something – hello, Theo Pinson! – there are also likely a lot of guys the Raptors are intrigued by who didn’t come in. Kostas Antetokounmpo seems the type to be high on their boards, and a number of the names they brought into Toronto are ranked within the team’s top 60 despite public opinion being a little less high on them.

Here’s what I wrote about trying to learn from the pre-draft process last week:

Primarily, that’s meant the Raptors’ staff has spent a good portion of the last few weeks on the road. With a finite number of workout dates around the NBA Draft Combine blackout days and the draft, the Raptors have prioritized larger scouting events that take the task of getting players to Toronto out of the equation. In addition to the combine in Chicago, the Raptors have attended agency showcases in Los Angeles, Las Vegas, New York, Chicago, and Miami, plus the NBA Global Camp in Italy (with a quick stop in to Lithuania to interview Sarunas Jasikevicius).

Those are imperfect environments, with workouts not in their control and interview time at least a little scarce. Still, it’s better than nothing and allows the Raptors to cast a wide net. The Raptors conducted more interviews at the combine this year than they normally do — they’re usually aggressive in this regard, anyway — knowing it would be hard to get players in.

Not only do they want to cast that net wide because of the potential for them to make a draft night trade, but the back end of the draft is considered to be relatively flat. That is, it’s a little hard to nail down what the second round might look like with less separation between picks and that part of the draft will likely come down to team preference and fit. Maybe the player you want requires you to secure a mid-second rounder? Maybe he slides out of the draft altogether?

In other words, the Raptors definitely have targets out there, and while the two dozen or so names they brought in might tip their hand, we’re dealing with a serious lack of information here in trying to figure out who they might like. Personally, I like the three names you mentioned (I have a strong Canadian bias, of course), Pinson, Khyri Thomas, Jarred Vanderbilt, Devon Hall, and a handful of others in the second to undrafted range. This draft is heavy on guys I’m intrigued by but not in love with, which might just be a byproduct of me having to cast such a wide net in draft prep this year (since the Raptors don’t have a pick range for me to focus in on) and therefore getting to catch up a little bit on a lot of guys rather than going super deep on a smaller handful of names.

It’s going to be pretty tough. In terms of a straight player-for-pick swap, I’d guess OG Anunoby is probably the team’s only prospect that can get you there straight up, and I’d find it hard to believe the team likes more than a small number of guys in this draft better than they like Anunoby. Were the Raptors’ cap sheet a little cleaner, it would be possible to wiggle in while giving up less in raw asset value to take on bad salary, but they’re not really in a position to do so unless A) their appetite for the luxury tax this year and next is larger than anticipated, or B) a motivated top-10 seller is willing to move terrible salary for plain bad salary. What might need to happen, then, is for the Raptors to make two separate deals, first flipping an asset for a lower first-round pick, then using that lower first-round pick to help move into the top 10 (so that the team trading the pick is moving down rather than out of the draft entirely). In all of these scenarios, Memphis’ willingness to move off of No. 4 to unload Chandler Parsons is relevant, though that is a downright terrible deal and I’m having trouble coming up with a framework that would make sense for Toronto. The Clippers could be a factor, too, with two lottery picks.

Of course, the discussion of moving into the top 10 is a little different if you’re willing to trade one of the team’s stars.

Trading stars

I’d pick against it happening at the draft. It’s always safer to bet on a deal not happening than one happening, especially one of that magnitude. A lot of frameworks for DeMar DeRozan make more sense on July 6, anyway, when there’s a bit more cap flexibility league-wide for the purposes of trades (this is where you’ll see trades reported or teams select players and then trade their draft rights shortly after). With that said, there are some interesting three-team ideas that you could kick around involving DeRozan and teams in the lottery.

In general, I think the team is earnestly looking at every possible means of improvement, and DeRozan is probably the team’s best chip for fundamentally changing the core and remaining competitive, both because he presents a bit of a stylistic bottleneck on both ends and because he probably has the highest trade value of any of the team’s higher-salaried players. My feelings on this are pretty complicated, though. As I wrote in the last mailbag:

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.

My opinion hasn’t really changed since then. You can trade DeRozan, and you should definitely be exploring it, but it has to be a pretty clear step in the right direction now or for a year or two down the line to sell it. It’s probably not worthwhile if you’re shuffling deck chairs. If Luka Doncic is sitting there, or some salary relief, a quality role player, and another pick? Absolutely, take a long hard look. I’m skeptical the right kind of deal presents itself tonight.

The Kyle Lowry situation is a little more straightforward. Given his age and salary, he is perhaps a little tougher to trade, but he’d also pretty seamlessly fit on about 30 rosters in the NBA given his style of play. The issue with dealing Lowry, even with strong point guard depth, is that you’re almost surely taking a step backward, and you’re probably not getting fair market value for his talent because of his contract (and again, you’re maybe taking on some bad money). You can sell me on improving via a DeRozan deal; if Lowry is dealt, that’s a tougher sell, and in that case I probably think it makes sense to also deal DeRozan and accept taking a short-term step-back to set yourself up for 2020-ish.

An email from Dave: Do you think the Raptors have reached what I’ll call the BlueJays turning point? The trade for Tony Fernandez / Fred McGriff being equivalent to Lowry / Derozan trade. As a necessary step in getting to the finals? Secondly would a sign and trade for Paul George work? Would this be enough to change the on court demeanor and add some edge? Would love to hear your thoughts.

I answered most of this one above. I don’t think it’s necessary – I’m a little skeptical about the Raptors reaching the finals with this core, anyway, given where the East is heading – but I think they’ve reached the point with this group where they can’t be committed to inertia and stability, because five years is a long time to bang your head against the wall. Changing coaches was a big step toward that end, and I really think they should explore roster changes, I’m just not sure the market is going to present the type of opportunities that will make those explorations bear fruit.

As for Paul George, a trade for him would require a sign-and-trade in July, and most rumors suggest George has already honed in on either staying in OKC or landing with the Lakers. So you’d have to sell him on Toronto and then find a deal that works under the cap and works for the Thunder logically, and that’s a tough one unless they really like DeRozan.

I do, yeah. I don’t think it’s the slam dunk that some in the Raptors community seem to be assuming. DeRozan has playoff limitations but he’s also a reasonably efficient high-volume scorer and draws more defensive attention than anyone on the roster, and I don’t think it’s safe to assume simply spreading his usage to other parts of the roster will be a net plus, even considering efficiency and defense. Everything would get harder for everyone else on the floor without DeRozan, save for playoff-type environments where defenses load up on non-DeRozan ball-handlers to leave him alone beyond the arc, and you can never rule out DeRozan coming back even better. At the same time, DeRozan is a limiting factor in how the team plays offensively and is their worst (or second-worst) rotation defender, both of which are real issues as the team looks to shift style and grow more dynamic, no matter how wonderful a person and player DeRozan is. As I outlined above, I think the set of circumstances where the Raptors deal DeRozan and improve immediately are pretty slim, but when you factor in age, the back end of the window, versatility in the playoffs, and so on, you can see it. Landing a quality role player who can soak up some of the minutes/touches and play better defense, then shifting some of that responsibility to the other young players, plus picking up a draft asset…you can get there.

Yeah, I’d need more back in that deal, or a third team looped in. The Parsons deal is super toxic, to where I’d probably only be willing to take it on if you ended up with No. 4 and another rotation asset, whether it’s from Memphis or a third team (the Clippers?). Complicating matters is that the Grizzlies reportedly want to move down, not out, so the Raptors would either need that third team or would need to pick up a first in a separate trade (Jakob Poeltl might have enough value to land a mid-first), then revisit with Memphis. The Parsons contract…woof.

It doesn’t work straight up without a third team or the Clippers sending out more salary (adding Boban Marjanovic makes it work, and he and Tobias Harris are best buds). The logic for the Clippers would be that they receive a home-grown superstar to sell to the L.A. market, remain competitive, and remain relevant within the Los Angeles basketball landscape, which is something they allegedly really care about. DeRozan is really good, and a return home – probably with his own Nike shoe to celebrate the occasion – would be an easy sell, plus be enough to keep the Clippers pretty good and maybe help convince DeAndre Jordan to stick around. They also have two lottery picks, and if they don’t have the appetite for a proper step back and rebuild (this is Doc Rivers, after all), using at least one of those picks to try to upgrade your talent base makes sense. For the Raptors, Harris would be a really nice piece (he’s criminally underrated and adds some versatility at both ends), but unless a guy they really like is sliding to the back of the lottery, I’m not sure they’d deem this enough of a return, even with Harris and Marjanovic (or whoever) coming off the books at the end of 2018-19.

Yes. I addressed this above a bit, but I think he’s less likely to go than DeRozan given age, contract, trade value, and the reasons you’d be trading one of your stars. If Lowry isn’t on the roster in November, I think the Raptors have probably shifted in a slightly different direction than they’ve said they’re going.

I’m still struggling to find a home for Ibaka in trades that doesn’t see the Raptors end up taking on an even bigger contract for a more useful piece (like Nic Batum), and I’m not sure they’re willing to do that. I think at this point you’d probably have to pay with a pick in a straight-up unloading, and the Raptors probably aren’t going to be willing to do that again this summer. So, you either explore a swap of bad contracts, hope you can use Ibaka in a bigger framework, or accept him for what he is – a useful rotation piece who is overpaid and was over-used last season. That’s not a terrible thing to have if you consider the contract a sunk cost and don’t manage his role around his dollar amount.

Raptors in free agency

I don’t know if I could identify one individual player’s spot they need to upgrade, but I think it’s pretty clear that forward is a position of need. If Fred VanVleet returns, the team is flush at the point, and even with Lucas Nogueira likely outbound, they’ll have strong center depth with the option to play Serge Ibaka over a position. It’s the wing, and particularly the forward position, where they’re thin, then – DeMar DeRozan played about half his time at the three last year, OG Anunoby can play some four, and C.J. Miles had a really nice season but was probably over-leveraged at times (at least alongside DeRozan) in the postseason. Adding another piece to that wing mix – or rehabilitating the confidence and value of Norman Powell – would shore up the team’s weakest spot. Were I targeting something in free agency or trade, it would be a three/four or three/two type who can provide some more matchup flexibility. I don’t think you approach the summer with one guy’s role in mind to upgrade, though, you just see if you can add talent through any means. (There’s also the cloud of one of the bigger names moving, which would shuffle the depth chart and render this exercise moot.)

It’s a little hard to say until we see how draft night goes and how the Fred VanVleet situation trickles down, but at the most, the Raptors will probably have the taxpayer mid-level exception to spend. They also have the bi-annual exception available to them. Neither of those figures to land you a major name in a weaker free agent class, though the general lack of cap space around the league could make Masai Ujiri’s salesmanship an asset here. Personally, I don’t see the Raptors adding one beyond the bi-annual exception amount given their likely luxury tax bill – think a third center if Lucas Nogueira walks, or potentially a third point guard if VanVleet is out – but if you want to look into the $5-million range, there are some reasonably attractive names. Wayne Ellington would be an absolute best-case scenario (there’s almost no way he makes that little), while there are depth fliers like Mario Hezonja, Tyreke Evans, Ed Davis, Rudy Gay, and players in that range who might end up willing to take the MLE. Even these names might be aiming too high, though we’ll have a better idea of that market in a week or so. (Kyle O’Quinn, Seth Curry, James Ennis, Luc Mbah a Moute, Quincy Acy, and Mike Scott are other names that might be worth a look. I don’t know, it’s early to figure price ranges.)

NBA and non-NBA miscellaneous

To be completely honest, this is probably the least prepared I’ve felt for a draft since maybe 2012. For a few years after that, I was theScore’s draft coverage lead, and the 2013-2015 drafts were probably the sharpest I’ve been with this stuff. In 2016, the Raptors had two first-rounders, so I was scouring everywhere for intel on anyone who might be a first-round pick. Even last year, the early exit let me catch a pretty wide net catching up on video. This year has been tougher – the Raptors not having a pick has made narrowing my research focus more difficult, and the lack of DraftExpress content has made a rapid catch-up more difficult. The end result is that I feel like I know “enough” about a really large number of prospects (the draft is super flat and there are 133 names to consider when I aggregated in 14 different rankings from around the web) but I’m not as intimately enamored with anyone the way I was with, say, OG Anunoby last year.

With all of that said, I have Jaren Jackson Jr. and Luka Doncic at one-two on my hypothetical draft board, and I don’t really care if that runs against the DeAndre Ayton consensus. Ayton is a really nice prospect, but Doncic is historically unique as a prospect in statistical and quality of competition terms and Jackson Jr. might be one of the highest-upside defensive prospects in the draft in years. I have other names I like. From a strictly Raptors perspective, I’m always a Best Player Available believer, especially when the team already has strong depth and a number of deals could be on the table this summer. Get the guy you think is the best and work the rest out later. If that means a flier on Kostas Antetokounmpo, if it means trying to teach Theo Pinson to shoot, if it means adding another combo-guard and playing three-guard lineups a lot, whatever. Get talent where you can. That should be the logic at the top of the draft, too, and I think Doncic and Jackson Jr. are going to be the best players from this class.

I think it’s a really fun wrinkle for The Basketball Tournament, and the fact that you can have a walk-off bucket is pretty amazing. I don’t think it’s a legitimate option for the NBA at any point down the line – it’s a lot of change for not a major material change in the length and strategy of the end-game – but I’d love to see it trialed at Summer League, where overtime is a scheduling hassle and largely unnecessary and where the environment is a more fun, casual, lower-stakes place for things like a walk-off bucket or a giant score sign. It’s a really cool gimmick and some good forward thinking from Elam.

The NBA will have to try to do their best to legislate around such a double-cohort, but I have no idea what they might be able to do to protect against it. If you eliminate the one-and-done rule, there will be a draft year where there’s the regular crop of prospects plus the first class of high-school eligible picks. In terms of teams loading up for that draft, the built-in protection there is that it will be difficult to acquire extra draft assets commensurate with the double cohort – teams will know at least a little in advance when the change is coming, and picks for that year could become more tightly guarded as a result. There’s also an argument that a deeper draft would make the middle-tier picks less valuable on the market in relative terms since there’s more talent to choose from later, and the NBA should absolutely add a third round of the draft by this point to help further absorb the prospect spike and continue to build the G League system as a true in-house development pipeline.

Absolutely. The fourth installment of the now-storied Kazuchika Okada-Kenny Omega series of matches was the single best wrestling match I’ve ever seen. And while I’m hesitant to go back to that well as soon as Wrestle Kingdom again, here’s betting that Okada finally losing the title sees him respond by truck-sticking the G1 Climax tournament and going undefeated through it.

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