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A Toronto Raptors Trade Deadline Round Table

What in blazing tarnations will Masai do!? The Raptors Republic crew give their 5 cents or 0.0000013617 Bitcoin in wisdom.

We’re such a primitive species.

For one, we enjoy watching other humans sweat and bleed and yell and strategize to put a sphere in a hole. For two, despite the entertainment being about in-game action, we are, arguably, more excited and thrilled by trades and their prospects.

Gossip, rumours, [fractured] relationships, disgruntled parents, rip-offs, BETRAYAL. We salivate over all of it. The social beasts we are.

Anyway, that’s my primer for the Round Table.

Oh, wait, no it’s not. for RaptorsHQ [* spits on the ground *] wrote a perfect outline of the Raptors’ financial and personnel situation leading up to the deadline.

It’s helpful to me because as soon as I see a number and then a rule or explanation, my eyes bleed and my brain starts thinking about the rice cake nachos I’d rather chow and go and do that instead.


  • Toronto is a razor-thin 20 Gs below the tax line;
  • Goran Dragić, Isaac Bonga, and Yuta Watanabe are expiring;
  • If Toronto trades no one, they will have roughly $25 million under the tax next year

I asked some Raptor Republic compatriots – Oren, Mac, Kyle, and Manny – to give me their thoughts, alongside my own, on the trade deadline and what they think Toronto should do, what Toronto will do, and a wild and crazy prediction.

Buen provecho.

1. Should the Toronto Raptors sell, buy, or keep the status-quo (with some edgework)?


Toronto should find a player that Nick Nurse is willing to play. That’s all. I don’t care what you say, it’s disheartening to watch our best players in their prime play 43 minutes a game just to lose in the final minute. We need a bench boost and we need some scoring versatility.

Besides, Brooklyn, Chicago, and Miami all have health issues, the Raps ain’t scared of the Bucks, and Philli is a train heading nowhere. Now might be an opportunity to do a little post-season run.


I think the Raptors should be buyers, within reason. They should aggressively target a player of consequence that can help them this year and beyond, assuming they can get that player for a reasonable amount, which I think is one protected first-round pick plus a young player at most.

The core players have overachieved this season and the problems are so obvious, including the lack of a big who can put pressure on the rim in the pick-and-roll and defend the rim on the other end, as well as a floor-spacing guard to come off the bench. Those are the two pressing needs for the team and solving even one would improve the team dramatically, in my opinion.


I believe the Raptors should be buyers at the trade deadline. Outside of maybe a fully healthy Brooklyn Nets team, I think the Raptors can compete with every team in the Eastern Conference once they shore up their bench scoring.


It feels like we’ve had some version of this conversation in every single year of Masai’s tenure in Toronto, and every single year the Raptors opt to maintain the status quo. There’s no reason to believe they’ll do otherwise in 2022. Personally, I’m all for a big flashy trade that shakes up the core of this team – but only if the future isn’t mortgaged in the process.


I think they should stay put but try to acquire bench help ASAP. If they can land a big man, without giving up much (like packaging a couple of second-rounders with someone that’s not in the rotation) that would be the most ideal move.

Championship aspirations aren’t there this season but the will to win will never go away with a team spearheaded by Fred VanVleet, Nick Nurse, Masai Ujiri, and Bobby Webster.

2. What do you think Toronto will do?


I think this team is a year away. Scottie, OG, Gary, and Precious all need a year’s worth of experience in their new roles. Pascal and Freddy are at their heights for the next few.

I’m genuinely torn on Chris Boucher. I think Toronto trades him. He’s playing stupendously and will want a longer-term contract next year (he’s 29 and has to think this is his last shot at a big contract). He fits so well with what Toronto wants and needs, but his frame and lack of consistent shooting doesn’t make him THAT MUCH more valuable than Precious.

Pulling a Norman Powell and turning Boucher into a younger, longer-term player makes too much sense.


I think they will be aggressive, actually. The Raptors know that they have to build their team through the trade market (and draft) rather than through free agency, and they have spoken in the past about giving the core players a legitimate platform to perform. I think they not only value getting the young players playoff reps but they also value putting their best players in the best positions to succeed, and without improvements to the roster, they aren’t doing that.

Sure, the Raptors could sit back, sell, get a high first-round pick and try to compete next season, but tanking begets tanking and I think it’s a dangerous road to go down, especially when your best players are playing this well. It was one thing to sit out the Tampa Bay season. It would be another to do it again, so I think the Raptors will try to improve at the deadline.

However, they have put themselves in a good position to be flexible, so if it turns out to be a sellers’ market, I could see them pivoting in that direction.


I think the Raptors will look to acquire another guard that can create their own shot and score at all three levels of the court. We rank last in bench production and our key starters rank near and/or at the top of the league in minutes played. Doesn’t seem like a sustainable formula with 30+ games remaining, so I worry about the durability of OG, Siakam, and, especially, Fred Vanvleet.


Don’t expect anything more than a minor move to get under the luxury tax. If they do make a trade it’ll be for a rotation big or a bench scorer, rather than a super-duper-star that raises the ceiling of this team.


I think they’ll end up trading Boucher if they can’t acquire someone to boost the second unit. He was the most likely to be traded before the season began and a contender would certainly benefit from his energy.

I think the Raps want to push for the playoffs this season: they’re either going to go for it or try to get the most out of their assets. It doesn’t hurt that Boucher is on an extremely team-friendly contract but it does hurt that it expires after this season.

Bottom line, if Toronto can find someone to accompany Boucher off the bench, they keep him. If they can’t, they trade him. That’s without even considering Goran Dragić. I definitely see the Raps trying to move him since both parties have reportedly agreed that’s the best way to move forward. Dragić doesn’t factor into the Raps future and could help out a contender. His contract isn’t that bad and it’s expiring so whoever gets him will have some wiggle room this summer.

We all know “cap space” has become one of the sexiest terms in the league. I really have no idea how this plays out but I think if Dragić is outgoing, there’s likely to be draft compensation incoming, especially if it’s an ugly contract.

3. What are your favourite trade ideas?

Chris Boucher Time Machine

Toronto: Elfrid Payton + Jalen Smith + 2023 protected 1st round

Phoenix: Chris Boucher + Svi Mykhailiuk

Elfrid Payton ain’t great; he can buy Toronto ball handler minutes when needed. Jalen Smith is the prize; Boucher → Jalen is the equivalent of a Norm → GTJ. A protected 1st (or a 2nd round pick) is compensation for Jalen being a UFA and Elfrid having a year left. Suns need depth for their playoff-push.

Another Gary Guard

Toronto: Gary Harris

Orlando: Goran Dragić + Malachi Flynn + 2023 2nd round

Orlando might be able to get more for Harris, but he’s inconsistent and his contract is expiring. He’s exactly the kind of “semi-project” Masai loves and seamlessly backs up Gary Trent Jr.

Any Clipper

Toronto: Serge Ibaka + Luke Kennard

LAC: Goran Dragić + Malachi Flynn + 2023 2nd round + 2025 2nd round

We need a shooter and bringing Serge home is worth all Flynn’s weight in gold. Clippers could blow this puppy up and shed contracts. I’d take any of Justice Winslow (I WILL NEVER GIVE UP ON HIM), Isaiah Hartenstein, or evennnn Marcus Morris instead.

Myles Turner in the Middle

Toronto: Myles Turner

Indiana: Goran Dragić + Malachi Flynn + 202* 1st round

Something like Goran Dragić, Malachi Flynn, and a first-round draft pick for Turner. I think he helps a ton on both ends of the floor and while he is an imperfect player, the Raptors can hide some of those weaknesses. He is also young and signed for two years.

Jakob Pöltl Return

Toronto: Jakob Pöltl

San Antonio: Chris Boucher + 202* 1st round

Something like Chris Boucher and a first-round pick for Pöltl. We know he can succeed beside Pascal Siakam and while he is not a shooter, he provides spacing as a roll threat and good screener/cutter. He is also an elite defensive player.

Nickeil Alexander-Walker Back to Canada

Toronto: Nickeil Alexander-Walker

New Orleans: Yuta Watanabe + Malachi Flynn + 202* 2nd round

Something like Yuta Watanabe, Malachi Flynn, and a second-round pick for NAW. I like his upside a lot and what he showed with the Canadian men’s national team. He provides the ability to get downhill and is really crafty at the rim. You have to believe that his outside shot can improve; I would bet on it.

Pacers Pickings

Toronto: Caris Levert + Justin Holiday

Indiana: Goran Dragić + Malachi Flynn + 2022 2nd round

The Pacers are my favourite trade partner for the Raptors. They are looking to reset and a part of resetting is opening up cap flexibility for the future.

This deal provides the Raptors with a proven scorer off the bench and additional shooting at the wing position. Also, as mentioned before, the Pacers get cap flexibility with Goran’s expiring contract as well as a young PG that has shown promise when given consistent opportunities.

Myles High

Toronto: Myles Turner

Indiana: Chris Boucher + a 202* protected 1st round

Myles Turner seems like a fun piece, but the price is likely too high. Sending out Boucher and a protected pick for Turner would be a coup de grâce for this team and its long-suffering centre rotation, but it’s likely that offer will be outbid on the open market.

Go-to-I-ran Dragić

Toronto: cake crumbs

Anyone in the world: Goran Dragić

In addition, I’m in favour of any move that gets Goran Dragić as far away from this team as humanly possible. Do the Guangdong Tigers need a new starting point guard?

Striking it KenRich

Toronto: Kenrich Williams

Oklahoma City Thunder: Malachi Flynn + 2027 2nd round

Seeing as Flynn isn’t getting any run, it wouldn’t be crazy to think the Raptors would ship him off and if they attach a second-rounder or two, OKC would probably listen. Kenrich Williams is 27 and probably doesn’t fit into their long-term plans. He could help Toronto off the bench and fill in as a backup two, three, or four. Dude’s averaging 7.1 points, 4.1 boards, and shooting 39.3% from distance.

4. Gimme one wild prediction


Masai swings at fences. Not the ones protecting someone’s small, little yellowy-green iota of grass. Not picket-fence swings. Outta-the-ballpark swings.

To do that, he’s gotta have heavy-duty leverage. To find that, you need a desperate team or unhappy player. And do it all without losing the core 4. That’s tough criteria. How about this:

Toronto: Jusuf Nurkić + Norman Powell

Portland: Goran Dragić + Khem Birch + Malachi Flynn + 2023 1st round

Despite just beating Toronto, Portland’s season is finito. It might want to shed money and do a minor reset. Nasir Little and Anfernee Simons will get paid.

Toronto needs a scoring guard and a Marc Gasol-type desperately. Jusuf is expiring; Norm’s contract is a bit beyond Toronto’s timeline, but he’s always flippable (Lakers are going to be desperate for 3 more years). We take Norm’s money, you give us Jusuf. Hate to lose Khem, but that’s showbiz baby. They may try to extract Precious…mmm…okay.


My wild prediction is that the Raptors trade a first-round pick and salary filler / young players to improve the roster.

I would guess they try to hold onto Precious Achiuwa, who Masai Ujiri admitted he was biased about. It wouldn’t shock me if they moved on from GTJ, though they would need shooting in return. So maybe they trade for Turner, Pöltl, Richaun Holmes or at the very least Dwight Powell.

My other wild prediction is that they make it to the play-in tournament, advance, and lose in the first round (wild, I know!). That would be a very successful year for them, IMO.


Hmmm… One wild prediction would be the Raptors re-acquiring Norman Powell at the deadline.

Toronto: Norman Powell + Robert Covington

Portland: Goran Dragić + Chris Boucher + top 20 protected 2022 1st round


Toronto hops into a Ben Simmons trade and gets an asset back from a third team. The Raptors have no need for Simmons himself, but would certainly love to be at the negotiating table in a huge deal that changes the landscape of the league. This could be as simple as shipping one (or both) of Boucher and Dragić to a contender in exchange for a young big, or it could be something more bold with Toronto including Siakam/OG in exchange for a true blue-chip asset.


I wanted to say Gary Trent Jr. gets a quadruple-double but that’s not trade-related.

Toronto: 202* 1st round

Anybody: Malachi Flynn

Toronto’s front office could sell an ice cube to a Snowman – especially, if the other front office is Sacramento. But then again, if it is Sactown, it’s not saying much, since I always wonder what’s going on over there anyway.