Raptors Trade Deadline Mailbag: Who might be dealt by Thursday?

We’ve been dealt a bad hand for our annual pre-trade deadline pieces this year, thanks to the Raptors jumping the market and making their two biggest trades early. Still, it’s not quite 2-7 offsuit, and so we’ll see the flop here and answer as many of your deadline mailbag questions as we can.

I can’t get to everything, so apologies if I missed your Q, and thank you for all the submissions. I prioritized deadline-related questions where necessary, versus some of the bigger-picture questions I received. Some questions have been edited for brevity and clarity, as well.

Let’s get it.

What is the likelihood of Bruce Brown, Chris Boucher, Dennis Schroder, Gary Trent Jr., and others, are still here after the deadline? - Multiple

Let’s not waste any time. With the Raptors having dealt their two biggest chips, the focus now narrows on their handful of capable role players and specialists. Beyond Brown, it’s hard to gauge the market, as there are a number of similarly-calibred players available, and the four Raptors mentioned all have contracts large enough to necessitate taking a real salary back. Let’s go through them individually.

Brown — He easily has the largest market of the bunch. Most contenders who aren’t super-leveraged into the second tax apron would (or do) have interest, as Brown fits everywhere and was recently a key piece on a championship team. He also offers rare contractual flexibility, with a fully non-guaranteed team option for next year. The sticking point here could be that the Raptors can just opt to keep Brown, execute the option, and shop him again in the summer as a win-now expiring, or keep the 27-year-old with this younger group. 

I’d lean toward Brown being dealt, and while the initial reporting of multiple firsts seems like wishcasting, a package of a matching salary, a solid prospect, and either a late first or good second doesn’t seem out of the realm of possibility. Would the Raptors – or you, reader – just opt to keep Brown if a B-level prospect and another pick in the early-30s is the best offer?

Boucher — I mentioned on The Raptors Show after the Pascal Siakam trade that Boucher was very available, and that remains the case, as far as I can tell. Even with Boucher mostly out of the rotation, contending teams know what he can do as an energy big off the bench, especially if he’s in lineups that make a bit more sense for him, versus some of the space-free redundant second units Toronto has run. 

The Raptors aren’t going to get a ton back here, not with Boucher owed $10.8 million next year and so many teams prioritizing flexibility. I think they’d take a decent second, if it became available. My biggest curiosity here is if the Raptors would take back long-term money to get a better asset, or if they’d prioritize clearing Boucher’s $10.8 million for next year off the books for even more summer flexibility.

Schroder — There hasn’t been much smoke around Schroder. He’s on a reasonable deal for a good backup point guard, making $13 million in the final year of his contract next year. But the market for backup point guards is pretty deep, and most competitive teams would have to send back a useful player to make the cap math work. We know Darko Rajakovic is a big Schroder fan, and even developing teams need quality vets around. 

Some of the trades I got suggested for Schroder seem to overstate his market. I think expectations should be muted here. He was available this summer to any team with a mid-level and has performed exactly as expected. Reliability and projectability is good, but there probably won’t be a lineup of teams attaching quality assets (plus matching salaries) for a guy you could have signed in July.

Trent — This situation has been difficult to get a consistent read on for years now. I felt last deadline that he was the likeliest to move, then they bought instead. There was reporting in the summer an extension was close, but I was very certain that wasn’t the case. Now, Trent has probably lost money by picking up his player option, but he’s playing his best ball of the season of late. Quality teams should value Trent’s shooting and the ability to acquire his Bird rights via trade, so they can exceed the cap to re-sign him this summer. Those are valuable to Toronto, too, and Trent is still just 25. I’ve just never been able to get a read on the Raptors’ long-term commitment to Trent, and it’s possible that’s because they haven’t, either.

The others — Thad Young can still play and can fit into a handful of teams’ traded player exceptions at $8 million. Otto Porter Jr. was a rotation contributor on a champion less than two years ago, is theoretically healthy, and only makes $6.3 million. You could probably get either of those guys for a second, and, failing that, Porter could be headed to the buyout market. … The team seems committed to Jakob Poeltl longer-term, though the Steven Adams trade certainly suggests there’d be a good market for him. … Jalen McDaniels and the $4.7-million owed to him next year probably aren’t enticing anyone unless it’s to make the cap math work on a larger deal.

You can see every team’s relevant exceptions, contracts, cash status, and draft picks in my trade deadline asset sheet here.

Is a player untradeable if they’re injured? Does this explain Boucher’s minutes lately? - GG

A player can still be dealt if hurt, but it would alter their market and require the acquiring team to be comfortable with the medicals. Boucher has been on the fringes of the Raptors rotation at a few different times this year, but the timing of him getting a few DNP-CDs is certainly interesting.

Can the Raptors extend Trent if they don’t trade him? What can they offer him? - S

Unless they’ve kept it extremely quiet, the Raptors and Trent’s camp haven’t engaged much on a new deal during the season. If he’s still on the roster past Feb. 8, they could revisit. Unlike the OG Anunoby extension situation, Trent’s maximum extension is well above what he’d command in free agency, so there’s room to find a deal. The likelier scenario at that point becomes Trent hitting unrestricted free agency and gauging his market — it’s why he exercised his player option to bet on himself in the first place —  while the Raptors hold his Bird rights to either re-sign or sign-and-trade him.

Will the Raptors value having tradeable contracts for the summer and next season, leading them to keep Schroder or Boucher? - Foster

I get the thinking here, that “flexibility” includes the ability to make salary math work. You don’t want another 2016 deadline where literally the only mid-sized contract you have to make trades is Patrick Patterson, and you want to keep him. With that said, there are two factors to consider here. The first is that the Raptors project to be a team with significant cap space this summer, and you don’t need to follow all those salary-matching rules if you have cap space to just absorb contracts instead. The second is that they’ll eventually sign someone next summer, too, so if you’re worried about 2024-25 in-season trades, there will be new contracts that are movable. It’s probably a small factor they’ll consider here, it just won’t turn them away from a good deal if it’s there. 

If the Raptors have an opportunity to buy a young-ish player with term using draft capital, should they? - Spen and Will

This is a great question, given that the Raptors now have additional draft assets and Masai Ujiri basically told us they won’t be using all these picks in a single draft. The idea here would be that current pro players are more certain and closer to helping you win than theoretical picks, and if the Raptors don’t want to be in the rebuilding wilderness for too long, they can expedite building around the Scottie Barnes-Immanuel Quickley-RJ Barrett core by trading for another piece ready to contribute now and still grow long-term.

I’d be a little bit surprised if this kind of opportunity materialized so soon, just because it’s hard to find a team that would want a Brown or Trent type, also want picks back, and move off a good young player. With that said, multi-team deals are always possible. I’d love to wishcast a three-team deal that frees one or two prospects from the Pelicans, for example. It feels likelier they explore this at draft time, but not ruling it out.

Is there a big with upside they could package pieces together to target? - Nat and others

There isn’t a clear and obvious answer here, though I think they should absolutely be looking. Dallas has maintained they’re not moving Derrick Lively Jr. Are they firm on that? Someone else (Trevor) mentioned Isaiah Stewart, but he’s injured right now and subject to what’s known as the poison-pill provision since he just signed an extension, so cap math gets a bit hard. Nic Claxton is probably the closest answer I have, although as Luis and a few others asked, it might make more sense to just try to sign him as a UFA this summer. It’s always preferable to acquire a player via trade and hold their Bird rights for flexibility, but that’s not worth a significant asset if you have ample cap space.

There’s also usually someone out there you didn’t think was available who actually was. I don’t have a strong preference for addressing a specific position, because the team just needs talent in the door right now, but finding a young big who fits the existing core should be a priority in the next six months or so.

Who are your favourite need-more-opportunity young players the Raptors could pursue? Could you see them dangling a first this year for a P.J. Washington type? - Mark

I think my initial list that identified Quickley still mostly holds up for targets although it wouldn’t be as guard-heavy if I did it today. I think Washington is probably below the line of upside for which I’d give up one of the picks you just received, as he’s now 25 and earning his market value. He’s a good player, I think you just want to try to identify that guy before the (reasonable) pay day, if you’re giving up a pick, or before he becomes who he’s going to be (saving you the pick, perhaps). 

If I have time before Thursday, I’ll update that earlier piece with a few more names

Beyond Barnes, is there truly another untouchable on the team? And what’s the line on Barnes being untouchable? - Mark

“Untouchable” always includes some caveats. In Barnes’s case, with where the team is competitively, there’s just no realistic scenario (that I can see) in which you’d get a better young player with higher upside, so you’d never really consider moving him. As for the others, nobody is untouchable. It would take a lot to move Quickley so soon after acquiring him as a guy you see as a long-term fit with Barnes. Barrett has been great but we’re a few weeks removed from him being considered a neutral asset in trade because of the contract. “Untouchable” usually means “I don’t see a deal where trading them would make sense…right now.”

Is it a crazy idea to think about trading Scottie? Is there going to be enough of a window to contend before he’s a UF? - Mike

Barnes will almost surely sign his rookie-scale max extension this summer, meaning he’ll be under contract for six more years before becoming a UFA. Guys can always ask out via trade before then, but his only other path to UFA earlier is to not sign a max extension and instead play out his fifth year on a one-year deal, which is way more risk than anyone has ever taken before if they’re a max-level guy, especially with the new potential super-max escalators a team can incentivize.

If you don’t think you can build around an All-Star and potentially All-NBA calibre 22-year-old in six-and-a-half years, I think you need to reconsider a lot of what you’re doing. Trading Barnes now would set you back even further, just hoping some of the pick equity you picked up eventually became as good as Barnes. He’s 22! To reframe your question more pragmatically, yes, the extension this summer kind of sets a timer on when you need to compete with Barnes, but you don’t need to worry yet about free agency in 2030.

How much of their cap space will they actually use this summer, and will they use it for free agents, trades, or to take on bad contracts? - Marx and Jack

This is the question of June/July for me right now. The framing of the question really does highlight why cap flexibility can be helpful even if you don’t like the free agent class. Sign players, take back money in trade, eat a bad deal to pick up assets, etc; there are a lot of ways to leverage that space. I’m going to cop out a bit here and say let’s see how things look on Friday (I’ll write about it then), but it definitely seems from talking to people around the league that the stricter penalties and roster-building restrictions for deep-tax teams are going to create a window for flexible teams to be predatory this summer.

There were a few questions about taking on bad or just longer contracts to make deals happen, like Rui Hacihmura and DeAngelo Russell, or just taking on bad money in the short-term to help a team lessen their luxury tax bill. Those aren’t the sexiest trades, but they’ll almost certainly include draft and/or prospect capital attached to them. The Raptors will have to weigh the opportunity cost of making that commitment now versus holding maximum flexibility in the summer, but it would not at all surprise me in the short-term if they rent out the approximately $9 million in space they have below the luxury tax right now.

And yes, to Foster and some others, re-signing Anunoby or Siakam is technically legal, I just wouldn’t expect it.

What are the Raptors biggest areas of need? - Ramy

Talent. I get fit and skill specificity and everything, but they need to get as much talent in the door as possible right now and figure out the fit and the complementary pieces as they go. You absolutely prioritize pieces that fit with what you already have – getting some extra shooting in the door, a backup centre with some defensive chops, a bit more size at the forward spots – but really you just need the highest-upside talent you can get in trade right now to build back up.

If the Raptors need to waive someone to make a trade, who will it be? - Connor

Otto Porter Jr. if they haven’t found a trade home for him. He seems destined for the buyout market if he’s not dealt. Kira Lewis Jr. would probably be up next given he’s a free agent and they haven’t used him yet, but my preference would be to keep whatever moderately interesting young guys you can.

If Christian Koloko is cleared by the NBA to play, can the Raptors re-sign him? - Michael

They could. He’s cleared waivers and is now a free agent. If they wanted to bring him back with Raptors 905 or as a two-way player and have him come back through the G League, they would have to wait until the off-season to do that.

What happened to the game I loved? - Stevie

The thing about the old days…they the old days.

Should the Raptors target Dijak when his contract expires this summer? He’s 6-foot-7 and can work with his eyes closed. - Ethan

No. He’s sneaky old for a developmental system prospect. Doesn’t fit the timeline. I’d rather feast my eyes on someone younger.

Which of Thad, Otto, and Garrett Temple would you have wanted in their prime? - Dylan

Excellent question. I’m taking Porter. He was never the scorer or passer Young was, but Porter had a four-year peak as a 41.5-percent 3-point shooter who guarded the other team’s best player every night, and he was actually an ironman in those early peak years. Young had a much longer and more role-versatile peak but didn’t reach as high a high. Temple can be my union rep in any era.

Would you rather be the Charlotte Hornets? - Crystal Ballin

Even with the jerseys and court and Ball-Miller-Williams core, literally never. The Hornets? I can’t abide. We have to want more for ourselves, etc, etc.

Are you (and other members of the media) upset at the direction Masai chose? - 604 Hoops

Not at all. I’ve been writing and talking about the need to choose a direction with more conviction for two years now. While I can understand why it didn’t happen sooner, my concerns about the opportunity costs of waiting have been confirmed, in my opinion. Trying to win and develop meant they weren’t optimizing either path, and they probably could have gotten the retooling moving a little sooner. 

I can’t speak for other media, and good basketball is certainly more fun to cover than bad basketball, but analyzing the team and their moves isn’t about me. I’m just glad there’s a plan and I can analyze the team through that lens from here. Hopefully it leads to another 2016-20 era that was so fun to cover.

How do you stop this team from letting go of the rope? - Omar

You hope, foremost, that Thursday passing puts some guys at ease and lets them just focus on the task at hand. You also have some more role certainty after that date, as you know who’s around for this year, long term, gone for good, just biding time, and so on, with clarity. Mostly, though, it has to be clear to these guys that they’re playing for their NBA futures. The lack of intensity and energy this team’s shown at times has been perplexing given how much, individually, everyone has on the line. The post-deadline identity needs to be a team of hungry young guys seeing your full pockets, not a bunch of guys playing out the end of a 30-win year.