If the Raptors are sellers now, who do they sell to?

As we covered in my last post, the Raptors are at a bit of a crossroads. They could try to contend for a home court playoff berth again this year, and if all goes well even get one, but then the following year they have a large portion of their roster heading to unrestricted free agency. So success this season may not carry over.

That means the one avenue Toronto should consider is to sell those veteran players for a draft asset return. Now, it may be difficult to get value for overpriced veterans if the Raps insist on swapping expiring contracts. Still, let’s assume for this exercise that the Raptors are punting on their 2020 cap room, can take back two-year contracts with impunity (but no longer than that to preserve 2021 cap room), and will use that to maximize the prospect/pick return they can get for each of Serge Ibaka, Marc Gasol, and yes, Kyle Lowry.

Fred VanVleet is also a key UFA that summer, but for now we’ll focus on the veterans, considering the team may want to keep VanVleet moving forward even if they are rebuilding. And one would expect with his age, lower salary and recent Finals performance, he’d be far easier to find a match for if it came to it.

So, for the sake of exploring all the options, here are a few teams and players I think make a good match for such a deal with Toronto. Remember, these are deals where the Raptors are punting their 2020 cap space, so expect to see some less desirable contracts come back.

Boston Celtics

Gordon Hayward ($32.7M) for Marc Gasol ($25.6M) and Malcolm Miller ($1.6M)

The Celtics want to compete now, they just signed Kemba Walker, they still have their young, ball-dominant wing prospects, and there’s only so much ball to go around, as they found out last season. Meanwhile, they lost Al Horford in free agency, and essentially have no real centres on the roster. This move would let them compete this year, see where they stand next summer, then either re-up Gasol or find another solution down the middle. Miller gives them a cheap backup wing depth option, while his chances here seem limited yet again by the acquisition of Stanley Johnson and Rondae Hollis-Jefferson, so it’s little opportunity cost for the Raptors.

It’s a salary saving move this year for the Celtics, and sheds Hayward’s entire 2020 salary ($34.2M). The Raptors could use a wing scorer, and maybe could pump his value with a year here and be able to flip him for more assets next summer. Hayward’s trade kicker could have caused issues, but he is already earning the maximum salary this year, so it would not increase his salary at all (well, by a few tens of thousands of dollars, not enough to break the trade math).

The Celtics would need to pay an asset price here. The good news is, the Celtics are still flush with draft picks. They have a particularly inviting 2020 top-6-protected (for one year) pick from the Grizzlies. But if that’s too valuable an asset, they also have all their own first rounders as well as a first from the Bucks in 2020.

Charlotte Hornets

Nicolas Batum ($25.6M) for Serge Ibaka ($23.3M) or Marc Gasol ($25.6M)

This deal can be salary neutral or save the Hornets a little cash this year, while in either case they shed Batum’s player option year (that he will almost certainly opt into) for next summer.

Charlotte is hard to peg, but they would surely like to get out of that contract, and with the signing Terry Rozier, it looks like they are trying to compete. They don’t have a lot of big depth beyond Cody Zeller, unless Bismack Biyombo counts (he doesn’t). Adding a veteran big man (who can play both the 4 and 5 in Ibaka’s case) could be appealing to them.

Again, it’s a situation where the upgrade alone may not be worth draft assets, but the upgrade in combination with the salary savings could get it done. And Charlotte has all their first round picks available to trade.

Dallas Mavericks

Tim Hardaway Jr ($20M) for Serge Ibaka ($23.3M)

Here Dallas uses its remaining cap space first, and then can complete this trade using salary matching rules operating over the cap. Dallas is looking to compete, and having additional 4/5 depth behind Kristaps Porzingis, Maxi Kleber, and Dwight Powell — especially experienced depth — could be of value to them, especially if they want to give Porzingis the load management treatment as he returns from a lengthy injury. More importantly, just like the examples above, this lets them off the hook for Hardaway Jr.’s player option salary of $19 million next summer.

The Raptors probably don’t see much value in Hardaway Jr, but this is another case where some heavy usage on a half decent team could pump his value and let them move him again at the trade deadline for more assets. Or the next summer or deadline, if he opts into his deal. If he opts out, it’s just that much more cap space to do more of these deals in summer 2020 (at that point for expiring contracts).

Once again, the Raptors would obviously be hoping to extract some draft assets, but Dallas is a little shy on assets. This is one where the most likely return is a few second rounders rather than a valuable first rounder. This one goes to the bottom of the list. Unless, for example, the Mavericks would have interest in Norman Powell — if they want to increase their team salary and don’t mind taking on a little more in the far term in exchange for shedding some of Hardaway’s cap hit next year. They do have a large traded player exception (TPE) that would allow them to absorb Norm’s deal without matching salary. Getting off that 2021 salary owed to Powell may make this deal worth the Raptors’ time.

Miami Heat

Goran Dragic ($19.2M), Justise Winslow ($13M), Kelly Olynyk ($12.7M) for Kyle Lowry ($35M) and Malcolm Miller ($1.6M)

I’m having some trouble finding a valuable landing spot for Kyle Lowry — only a few teams need a PG, and even fewer both have the salary to match his contract and worthwhile assets to send back.

Miami is just the sort of team to make a move for a player like Lowry, especially if they can avoid the cap hit this year and next, as they are in some tax trouble. They’ve been rumoured to be interested in Russell Westbrook, but they’d be better off trading for Lowry, as the asset cost should be lower and they can probably keep him for much cheaper moving forward. On top of that, Lowry fits better beside Jimmy Butler anyway.

They’ve already tried to trade Goran Dragic, and would probably want him off the roster before the summer is out if they can manage it. Olynyk was rumoured in trades as well, and between him and Winslow the Heat would be clearing over $26 million in cap hit in summer 2020. Winslow would be the primary prospect cost in this deal, though the Raptors would likely insist on more prospect value, perhaps one or two of their recent draftees. Miami has no picks to trade, with their first rounders spoken for for a while and no second rounders for most of the next half-decade.

Honestly, this deal isn’t great value for the Raptors. The idea here is to find Lowry somewhere he can really compete, and one would hope a pairing of Lowry and Butler could propel the Heat into the top half of the playoff bracket. Another one to let slide to the bottom of the list, I think.

Oklahoma City Thunder

Steven Adams ($25.8M) for Serge Ibaka ($23.3M)

This one is simple. Oklahoma City is likely going to try blowing it up, but in any big Westbrook trade, they are likely to take back a bunch of salary. They’ll want to shed salary in any case, especially this year as they are in the tax. They save a little money this year with this deal, while completely removing Adams’ $28M salary next season.

The Raptors would likely ask for a pick, of which OKC now has plenty. I imagine with OKC rebuilding it would not be their own pick but some small portion of the haul they got from the Clippers for Paul George.

Orlando Magic

Evan Fournier ($17M), Markelle Fultz ($9.7M), DJ Augustin ($7.3M) for Kyle Lowry ($35M)

Here’s an interesting one. The Magic were a good team last year, and really were just missing a point guard. Jeff Weltman should be well aware of how good Lowry can be. And with this move the Magic could actually end up a home court playoff team in the first round. If they were going to re-sign Vucevic, they should go all in building around him.

The Raptors would be making a bet on Fultz here, but may also ask for a little more draft asset value — perhaps the rights to recent draftee Chuma Okeke, or some future first or second rounders, of which they have plenty.

That could be a deal both sides win. Hopefully the Magic would also be good enough that Lowry would be happy playing there, as that’s part of the point.

Portland Trail Blazers

Hassan Whiteside ($27.1M) for Serge Ibaka ($23.3M) or Marc Gasol ($25.6M)

This one is pretty straightforward. The Raptors offer an aspiring contender an upgrade at centre while they wait on Nurkic to get healthy, while adding some cash savings right up front to help with Portland’s significant tax burden.

The Raptors would ask for a first round pick. Can’t ask for too much though, as this is one deal where the Raptors are swapping expiring deals with Portland, so that future cap flexibility value isn’t there.

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I had a few other teams, but they didn’t quite stick. These are the best I could come up with for the kind of trade market the Raptors are in. From the above, I lean to the Gasol-to-Boston, Lowry-to-Orlando and Ibaka-to-Portland trade ideas.

Let me know if you have any similar trade ideas down below, and I can check to see if they work for you. Or, maybe I’m barking up entirely the wrong tree here? Do you have trade suggestions that aren’t in this format? Or even are used to try to win more this season rather than plan for a future off-season? Also, let me know if I’m off my rocker with any of these valuations and no team would ever consider doing these deals with Masai, or Masai would never consider doing these deals himself.

All salary info per basketballinsiders.com