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Offseason Mailbag: Villains, Serpents, and a whole lot of free agent scenarios

May 19th, 2017 at 10:44 AM
Aggregated By Sports Media 101

I wasn’t sure if I was going to do an early offseason #RRMailbag. For one, I figured it’d be too large and we’d push close to the 7,000-word record (update: we broke it, this is 8,200 words, which is why it’s unedited). For another, the commentary around the team was pretty negative at season’s end. And most of all, the answer to a lot of the pressing offseason questions is “I don’t know, but here’s what I would do,” which probably isn’t as helpful as predicting what the team might do. So the answers that follow will have some Ifs and scenario breakdowns, but the Raptors themselves give the impression they don’t know where exactly they’re headed yet, so the best we can do is lay out the possibilities. I also timed the call for questions early on a Monday so I wouldn’t take four days to put this together. Alas, they always take a while. I did, however, go back and dig up some questions I’ve been asked fairly often, even if I already answered them on Twitter, as I figure if one person is asking, others may have the same question.

We’ll try to do mini-mailbags when time allows during the offseason, at least until they draw repetitive. You can find all of the previous editions of the mailbag here, if, for whatever reason, you wanted to read old mailbags.

Before we go ahead: A reminder that we have a Patreon page at If you appreciate the content we produce, want to support RR, and have the means to do so, any contribution is greatly appreciated and will help us continue to do what we do (and try to do even more). You can also follow me on Twitter for, uhh, tweets, and on Facebook for all of my writing/podcasting/radio stuff. Validate me. You can also ask me questions at any time using #RRMailbag, and I’ll be sure to include them in the next mailbag, no matter how long between.

Alright, let’s get this money.


(Note: I originally made this intentionally terrible photo shop for the header image but it was too stretched out. Disappointing when your terrible esoteric photoshops are rendered even more uesless.)


Common non-mailbag questions

Does Kyle Lowry opting out mean he is negotiating with teams for 2018-19 and will be with the Raptors next season? Or does opting mean he doesn’t have to play the last year of his contract? Or something else?

Kyle Lowry is a free agent as of midnight on July 1. His option was for the 2017-18 season, and he had until seven days after the Raptors’ elimination to choose to exercise it. The Raptors still hold his full Bird rights in free agency, but he can go anywhere he’d like for next season now. So when people talked about Lowry’s four-year deal or having X number of years left, they were including the option year. We’ll run into this again with DeMar DeRozan, who holds a player option in the last year of his new contract, too.

For clarity, this is a little different than the options the team holds on their young players. Those options, which need to be exercised by Oct. 31, are for the following season. Basically, with rookie-scale contracts, the team has to make those decisions very early, while veteran options are usually closer to the end of the relevant year. So when the team eventually exercises options on Delon Wright, Jakob Poeltl, and Pascal Siakam this fall, those will be for 2018-19.

Should the Raptors let Lowry go and use the money on a different free agent / Who do you like in free agency if Lowry walks?

This is perhaps the biggest complication with Lowry’s impending free agency: If Lowry walks, the Raptors don’t actually have any means of replacing him on the market. The Raptors are in a position to retain Lowry and their other free agents because they hold Bird rights, which allow them to exceed the salary cap to keep them. But they don’t have those rights on other free agents, and so they’ll lack the space to sign any marquee name.

To wit, even if the Raptors renounced the rights to all four of their unrestricted free agents, they’d only project to have roughly $20 million in cap space, not enough to chase a star and maybe not even enough to chase a second-tier point guard. No stars are incoming to replace Lowry, at least not via the money saved by not signing him.

And that’s assuming the Raptors don’t re-sign Serge Ibaka, P.J. Tucker, or Patrick Patterson. Those players have cap holds that essentially eat the Raptors’ theoretical cap space, and if any of them are re-signed, they’ll eat into real cap space. Basically, the Raptors will only be free agent players if all four free agents walk. Otherwise, you’re looking at trades, development, and one of the mid-level exceptions (depending on where salary lands) to fortify the squad.

Do you think Coaching Rumor X is related to Dwane Casey and the Raptors?

I mean, maybe? There is going to be a ton of coaching movement over the next couple of months, and you’ll drive yourself crazy trying to figure if each is related to the Raptors. They keep things pretty quiet - I got the Patrick Mutombo news last year but that’s rare – and the honest truth is Toronto probably doesn’t know yet which way they’re heading with the staff.

Can the Raptors sign-and-trade Lowry (or Serge Ibaka, or whomever) to recoup assets while losing the player?

I feel like I’ve written about this a bunch of times already, but let me re-hash: The newer two collective bargaining agreements essentially killed the sign-and-trade option as most people seem to remember it. When Chris Bosh left, for example, the Raptors recouped a pair of picks by using the sign-and-trade, which benefited the Raptors, Bosh, and the Miami Heat.

But the newer versions of the CBA no longer allow a player to get a fifth year using the sign-and-trade, nor can they get the larger annual raises the team with their rights can offer. So in the case of Lowry, his contract in a sign-and-trade would be the exact dollar amount as if he signed somewhere else without it. There is absolutely no financial benefit to Lowry to going this route. If Lowry wants to go to Philadelphia, the 76ers can sign him using cap space. There’s no sense in them surrendering an asset to the Raptors if there’s no benefit to them or Lowry.

The sign-and-trade tool, now, is really about expanding a player’s potential destinations. If Lowry (or Ibaka, or whoever) wants to go to a team that can’t sign them into cap space, then a sign-and-trade becomes an option for that team. The Raptors have to play ball and be amenable to that, and they’d likely ask for compensation in return. The player would be impartial, financially. So the sign-and-trade is useful for flexibility, but because it doesn’t change the contract a player can get, it’s really not as important a weapon as it used to be. The Raptors can’t really bank on getting anything back – basically, they can charge the going rate to eat salary, otherwise the acquiring team could just dump a contract elsewhere for cheaper to clear the requisite cap space.

Raptors offseason

They didn’t, so apologies that I didn’t get to this question. I don’t think it would have made much of a difference. With how guard-heavy the draft is at the top and how big a need Philly has there, they were probably going to use at least one of their picks on a guard, and they were going to have a need at the position still. Maybe landing Markelle Fultz would have made chasing Lowry slightly less likely, but Lowry can play off ball and rookie point guards need help anyway.

It’s a really difficult decision, one I’ve written about a ton already. I’m a Trust the Process person in general, but I think I’d probably keep the core and make a coaching/system change.

There’s just too much equity that’s been built the last while, and too big a risk of turning away from the best run in franchise history only to wind up spending years in the wilderness again just trying to get back to this point. I’d move Serge Ibaka to center, if he’ll stay, keep Patrick Patterson if his value’s taken a hit, shop Jonas Valanciunas (for his sake and for luxury tax reasons), use the draft pick, and hope some of the young players can take a step forward. You don’t have much financial wiggle room to add in this scenario, so I’d be on the lookout for a trade that nets a shooter. Dwane Casey doesn’t deserve to lose his job in a vacuum, but I’d probably make a change there just to try something new. The Raptors still wouldn’t be a serious threat to the Cavaliers like that, but I’m a believer there’s real value in staying good for an extended period.

But I am, like, 55/45 on this. The scenario in which they blow it up is just as justifiable, and while the day-to-day would be a lot less enjoyable, it would renew optimism about eventually getting where the team wants to go. There are tear-down measures available, some good young pieces on the roster, and a landscape in which there may not be many teams tanking for very interesting 2018 and 2019 drafts.

I don’t mean to be wishy washy, but as I outlined here, there are good arguments for either approach.

Where are we getting that Lowry is sharply depreciating? Prior to his wrist injury, Lowry was having perhaps his best season yet, and was a down-ballot MVP candidate again based on most advanced metrics. Everything we have to measure a player’s impact on a team still suggests Lowry is the team’s most important and impactful player, even if DeRozan often feels like the star because he’s the most important scorer.

You can definitely make an argument for moving on from Lowry and pivoting to a restart, but saying Lowry’s already started declining is disingenuous. In general, diminutive point guards age quite poorly, so the back end of the deal would definitely be concerning, and it’s a massive, flexibility limiting decision to re-sign him. As you mention, though, Ujiri hasn’t often let players go for nothing, and I still think the team will lean toward keeping him if he wants to stay (a major if).

If Lowry walks, the Raptors almost certainly have to tear things down. A DeRozan-Ibaka core is first-round fodder, and the argument for keeping the core together falls apart if the ceiling and floor are suddenly both lower. Don’t let a 14-7 record against a soft schedule with middling offense confuse that the Raptors wouldn’t be nearly as good without Lowry. Joseph is fine, but he’s not Lowry, and he can become a free agent after next year, too. You also can’t go after another star, because you still don’t have meaningful cap space. In my opinion, the direction hinges entirely on Lowry – if he goes, any argument for staying the course gets really, really thin.

I think Lowry returning would mean you can keep Ibaka if you choose you want to, at least. Ibaka probably won’t be able to find a better competitive situation in his price range, at least among teams that need a big like him and have cap space. The big thing with him could be moving Valanciunas, as Ibaka’s been pretty clear he enjoys playing center at this point (and he’s much better suited to play there, anyway). You probably have to choose between Tucker and Patterson for luxury tax reasons, and who you choose will come down to price, what you do with the rest of the roster positionally, and whether Tucker decides he wants to ring-chase at a discount somewhere else. Lowry returning puts you in the driver seat to approach the other free agents how you’d like. But I can’t really put a percentage on it, given all the players just speak in generalities about their plans and priorities.

Reasonable? Sure. But it all depends on Lowry. Playoff confidence is probably some function like this:

Playoff Expectation = (Lowry return expectation) + (Lowry leave * Sneak in with rest of core) – (Lowry leave * Blow it up)

So depending on how you feel about those things, adjust playoff expectations accordingly.

I would imagine Ujiri has pretty close to unlimited leash with MLSE. He is a great leader and has their full trust and support. And MLSE is not going to turn their back on consistent success. You don’t really lose your job as team president for consistently being good and making moderate playoff runs, even if you spend a bit into the tax to do it. The value of the Raptors’ brand will continue to grow like that. Ujiri’s leash would only stand to become a question if the Raptors got bad accidentally or an intentional move to being bad stretched on too long.

The issue with dealing DeRozan is going to be that the draft happens nearly two weeks before free agency. The Raptors won’t know for sure what Lowry is doing, and so they won’t know for sure if they’re even willing to shop DeRozan (and you probably need to keep it very quiet if you do). You could come up with hypothetical scenarios, or maybe you get lucky and Lowry tells you his intentions ahead of time, but the most likely case is that if you end up dealing DeRozan, you’re dealing him for actual prospects and future picks rather than doing it in time to hold the actual pick in this year’s draft.

I think people’s expectations are a little out of line if they’re looking at a top-five pick for him, though. DeRozan is great, but the 76ers and Lakers have been bad for a long time now to get those picks, and they probably aren’t willing to cash them in at the first sign of a star. I can’t see Philly being interested in DeRozan in general, given his poor fit with the rest of their young core. The Lakers make more sense since Magic Johnson probably wants a star, DeRozan is from L.A.,  and Nike would be ecstatic, but he’s not a great fit with Luke Walton’s vision for basketball, the team is probably going to add yet another young guard in the draft.

I’m not sure what a reasonable expectation is for a DeRozan return. He’s a three-time All-Star, an elite scorer, improves every year, and is a consummate teammate, but he’ll be 28 this offseason, is owed a ton of money (roughly 27 percent of the cap) over the next four years (the final year a player option), is a minus defender, and it’s unclear how well he’d do if he weren’t the focal point of the …

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Tags: brady heslip, Bruno Caboclo, CARMELO ANTHONY, Columns, CORY JOSEPH, D-league, Demar Derozan, Demarre Carroll, Dwane Casey, gob, jakob poeltl, Jerry Stackhouse, Jonas Valanciunas, jughead, Kyle Lowry, marty scurll, MASAI UJIRI, NANDO DE COLO, neverest, nick nurse, P.J. TUCKER, Paul George, Raptors 905, raptors draft, raptors huskies, raptors mailbag, raptors summer league, raptors trades, Rex Kalamian, riverdale, SERGE IBAKA, the villain, Toronto Raptors

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