A new direction in 2021-22, and the possible trades that could catalyze it

It’s not exactly a secret. Masai has always loved the freakishly long, athletic, high-motor players who can play and defend several positions. He’s liked them since his very first draft in Toronto when he desperately tried to trade into the draft (Bryan Colangelo had traded their pick away to acquire Kyle Lowry) to select Giannis…

The post-Lowry era has now begun.

And with his departure, only four players remain from the Raptors’ Championship team, and two of them didn’t even play in the Finals.

Lowry was also the last link to the pre-Masai Raptors with Fred VanVleet and Pascal Siakam now becoming the longest tenured Raptors. And the only current players on the roster with more NBA experience than VanVleet and Siakam is Goran Dragic, who Masai reportedly tried to move to another team and will probably not end the season on the Raptors roster. He’s also the only player over the age of 28.

On top of all that, the Raptors chose not to sign any of the free agents Raptor fans were clamouring for, with the only new signings being players who weren’t in the league last season. Their big offseason moves were bringing in Precious Achiuwa (and Dragic) and re-signing Gary Trent Jr and Khem Birch. Well, and re-upping Masai, which was probably the most important offseason move.

If anyone was unsure what the direction the team was headed, I think it’s now become pretty clear.

RETOOL? REBUILD? RENOVATE?

The future is not now, for the Toronto Raptors. The drafting of Scottie Barnes and allowing Lowry to leave signaled they’re prioritizing the development of the younger players over winning this season. Or in the words of Bobby Webster, “philosophically, going young became a more desirable path.” So while the Raptors certainly could make the playoffs, they aren’t exclusively focused on it like they were for almost a decade. And the faster Raptor fans accept that fact, the easier the next season will be.

This doesn’t mean the Raptors are tanking. And until the Raptors start trading Siakam, VanVleet and/or OG Anunoby for draft picks, I wouldn’t start dreaming of Paolo Banchero or Chet Holmgren just yet. Although more on that in a moment.

There have been a lot of Raptor fans complaining about the trades or free agent signings the Raptors didn’t make. Richaun Holmes seems to have gone from a mediocre starting centre to a high impact big man who apparently would have changed the fortunes of the organization. And all over the course of free agency.

Lost in all the angst is that Holmes would have added MAYBE two or three more wins, which doesn’t magically turn the Raptors into a contender or even take them to another level. All it does is give a likely .500-ish team a big, long term contract for a mediocre player, which is something teams in the position the Raptors are currently in usually end up regret.

There is also a belief the Raptors got a bad deal for Lowry, but there are two things to remember about the deal. The first is that Masai and company had already decided they weren’t going to be spending big money on a free agent because, as Webster said, “once we saw some of the numbers [of the free agents they were targeting] it made sense to use the flexibility” to go towards an incoming contract like Dragic. So taking on Dragic didn’t prevent the Raptors from signing players like Richaun Holmes. They took on Dragic and his contract because they didn’t want to sign players like Holmes to long term contracts at the prices they were asking.

Secondly, people seem to be forgetting that Pat Riley runs the Miami Heat, and he’s never been known to be much of a pushover. While it’s conceivable that Masai COULD have gotten a first round pick, Riley very rarely trades away first round picks (he’s done it just three times in 14 years running the Heat) and outside of Tyler Herro (the Raptors apparently wanted Achiuwa over Herro, anyway) there really isn’t much on the Heat roster that the Raptors missed out on. A second round pick? Maybe, but the NBA moves second round picks like Disney puts out Marvel movies. It’s a regular occurrence, so they’re fairly easy to acquire if the Raptors so choose.

In the end, the Raptors coveted Achiuwa and they got the player they wanted. Plus, we don’t know if or what the Raptors could end up getting for Dragic, so it’s hard to judge this deal just yet.

I just want to reiterate not to sleep on Achiuwa. He’s not just a throw in and there’s a reason the Raptors wanted him.

So with free agency essentially over, at least for the Raptors, it’s time to look ahead and figure out what exactly is in store for this team.

A NEW, LONGER DIRECTION

The Raptors will probably head into the start of the season with more or less the roster they have right now. While the eventual starting lineup seems pretty much set, with VanVleet, OG, Pascal (when he returns from injury), Birch and either Trent Jr. or Dragic, the most interesting thing about the Raptors roster can be summed up with this Josh Lewenberg tweet:

Add Freddie Gillespie, who measured in at 6’9 with a wingspan of 7’5, to that list and you can really see a pattern emerge.

It’s not exactly a secret. Masai has always loved the freakishly long, athletic, high-motor players who can play and defend several positions. He’s liked them since his very first draft in Toronto when he desperately tried to trade into the draft (Bryan Colangelo had traded their pick away to acquire Kyle Lowry) to select Giannis Antetokounmpo (I’ll just let the irony of the fact that trading for Lowry prevented the Raptors from drafting Antetokounmpo sink in for a moment).

Masai’s fondness for long, athletic players is why he reached for the relatively unknown Bruno Coboclo in the next draft. While that was a failure, Siakam and OG were most definitely not.

When Masai took over running the Raptors, Lowry, DeMar DeRozan and a young Jonas Valanciunas, among others, were already on the roster. It was too much talent to simply gut the team and start again, so, after trading away some of the less desirable players (cough*Bargnani*cough) he went forward with the core he inherited until he was able to trade for Kawhi. And that, of course, led to the Raptors’ first-ever NBA Championship.

With Lowry now in Miami, Masai finally has the freedom to build the team the way he’s always wanted to. It’s one reason he chose Scottie Barnes over Jalen Suggs, despite Suggs being the more polished option. Barnes fits the positionless-type basketball that Masai has always wanted.

So what does this mean for the team?

THAT’S THE SOUND OF INEVITABILITY

On the court, we’re bound to eventually see a lineup that includes Barnes, OG, Siakam and Achiuwa, with possibly Birch or Boucher thrown in for good measure. While this lineup might have some trouble scoring in the half court, they’ll cause absolute havoc on the defensive end with seamless switching and intense pressure. They’ll also get out and run. A lot. This is the blueprint for the future of Raptors basketball. Look for Masai and company to get even more guys who fit this mold down the line.

What moves the Raptors make off the court depends a lot on the development of their young players, especially Barnes, as well as where they are in the standings. If his play demands he plays more minutes, it might push the Raptors to move one or two of the their bigger pieces to give Barnes a bigger role and more playing time. And if the Raptors aren’t among the top six or seven teams in the East, it could precipitate a change of direction for the franchise and going all in on a Scottie Barnes future.

While Barnes’ eventual future may be at the point guard position (the jury is out on this), he’s not there yet and should get most of his minutes at one of the forward positions. The problem is the Raptors are pretty loaded at that position, so if Barnes plays well enough, either Siakam or OG might end up being moved. And I can pretty much guarantee it’s not going to be OG.

PASCAL SIAKAM

I understand Siakam is a fairly polarizing player among Raptor fans. To some fans, because of his struggles in the bubble playoffs and in the half court as the number-one option, he’s trash. And to those who fondly remember the Finals and the regular season where he was an All Star and All NBA second team player, he’s untouchable. As mentioned in a previous article, the case for trading Siakam has nothing to do with his limitations as a player, but with where the team currently is and, more importantly, what they lack: a franchise player.

Siakam is in the prime of his career on a team that is years away from contending. He’s also the Raptor who will get the most return in a trade. Add the fact that moving him would give Barnes more playing time, and it’s likely that if the Raptors do decide to make a trade, Siakam is the prime target.

Masai has always been extremely patient when it comes to making moves. He’d rather simply not make a trade than make one he feels isn’t the best one he could get. So even if the Raptors decide to move him to one of the teams that are apparently interested in him, there’s not telling when a trade like that might happen, if at all.

Beyond Siakam, the other Raptor who could see their days in Toronto numbered is Chris Boucher.

CHRIS BOUCHER

Boucher is a long, athletic player who can even hit the three, so he seems to fit in with what the Raptors are building. And he’s Canadian. So why do I think he might be traded this season? Two reasons. Outside of Dragic, he’s the oldest player on the roster, and more importantly, he’s in the last year of a team friendly contract.

It’s hard to imagine that Boucher, with his defense and ability to spread the floor, won’t be sought after by lots of teams next summer. Of course, there aren’t many teams who are projected to have lots of salary cap room next summer, but things change quickly in the NBA.

On his own, Boucher probably wouldn’t get enough back in a trade to warrant his departure on its own, but packaged with someone else, the Raptors might get enough to think about trading him.

Then again, it wouldn’t surprise me in the least to see him still on the roster at the end of the season. He’s a hard worker, plays defense and is currently the only big who’s proven to be a threat from long range.

GARY TRENT JR.

The Raptors JUST signed him to a long term deal whose value seems predicated on Trent Jr.’s continued development as a scorer and improvement on the defensive end. And he’s only 22. Unfortunately, due to his below average size for the shooting guard position and inability to play and defend multiple positions he doesn’t really fit in with the new-look Raptors. He’s also not a great passer, with only Freddie Gillespie having a worse assist rate than Trent Jr. among returning players.

He does have potential as a shooter and scorer, which are skills the Raptors currently lack. Plus, $52 million over 4 years for a guard who at this point is only a decent shooter and scorer might end up being a negative for teams looking to trade with the Raptors.

FRED VANVLEET

So if the Raptors start skewing younger and looking for longer, multipositional players, it seems like VanVleet might not seem to fit in. And on the surface, moving him might seem like a good idea to open up playing time for Flynn or for Barnes if they want him to play time at point guard.

And while the Raptors certainly should be able to find team that would want him, what he brings to the team is far more valuable than what they’d get back in a trade. His leadership and championship experience is exactly what the young player would need to improve and understand the Raptors culture. After years of mentoring under Lowry it simply wouldn’t make sense to trade him.

OG ANUNOBY

Anunoby is just 24 years old and seems to be the prototypical Raptor. He can play several positions and guard all five. He’s made developmental improvements on offense every year, and is already one of the best defenders in the entire league. He’s not the best Raptor, but, right now, he’s the most untradeable on the roster.

GORAN DRAGIC

No list of players likely to be traded is not complete without mentioning Dragic. Unlike most Raptor fans, I feel for the guy. He obviously was disappointed to be traded away by the Heat, an organization for which he’s played for the last 7 years. And like Lowry, he turned 35 earlier this year and would like to finish up his career on a contender. The Raptors are not that. And at one point it looked inevitable he would be traded to Dallas to play with his countryman and friend, Luka Doncic. So when that trade didn’t go through, it’s understandable he would be disappointed and say some things he regrets in the heat of the moment. Unfortunately, Raptor fans don’t forgive easily.

Now Dragic would already be on another team’s roster if it were up to the Raptors, but apparently Dallas hesitated to take on his contract, even for one season. So far. I would actually be surprised if he’s still on the team when the regular season starts.

THE REST

While guys like Flynn, Achiuwa and even Birch should play important minutes for the team, they simply aren’t going to add much to any trade at this point. Expect both Flynn and Achiuwa to show developmental leaps this year. Flynn has showed so far in summer league he’s made improvements, and Achiuwa should benefit from the Raptors’ system that allows big men to shoot from outside and handle the ball more often.

So if the Raptors do end up making a trade or two, what should we expect?

WHAT TO EXPECT WHEN YOU’RE EXPECTING TO TRADE

When the Raptors had Vince Carter, they decided to surround him with veterans, which sped up the team’s development and launched them into their first playoff appearance, but it also limited their window. They brought in a carousel of over-30 veterans who helped them win immediately, but were on their last legs (including trading away their fifth pick in 1999 for a 31 year old Antonio Davis – passing up on guys like Richard Hamilton and Shawn Marion). Even if Vince had stayed healthy, this strategy was already beginning to backfire for the Raptors by their third playoff appearance, which was the last playoffs Carter would play as a Raptor.

So if Barnes does start looking like a potential superstar, even if he’s still a year or two away from really coming into his own, then in order to give the team as big a window as possible, it makes sense to surround him with players as close to his age as possible (with a few younger veterans sprinkled in for good measure).

Basically, if a big trade is made, expect the team to get younger. Unless Washington decides to give Bradley Beal away for Trent Jr. and Goran Dragic, the Raptors probably won’t be bringing in anyone over the age of 25 unless it’s for salary cap purposes.

And, as discussed, look for any players they target to be long, athletic, multipositional players who bring it on defense and defend multiple positions.

Let’s start with some of the more discussed teams:

SIAKAM TO WARRIORS

This would be basically be the deal Golden State was supposedly offering before the draft, but would also include Dragic (who would be a great fit for the Warriors) and instead of the Warriors’ draft picks, would include the actual rookies (not sure if they would agree to sending both, but it doesn’t hurt to try). While the Raptors might have preferred to make the picks themselves, both Kuminga and Moody actually fit right in with the Raptors with their length and athleticism. Both of them would give the Raptors needed scoring, with Moody projected to be a good outside shooter. Wiseman would give the Raptors a legit 7-footer who could end up being the franchise centre they lost when Marc Gasol left. Wiggins could probably be moved to another team, but if not, he would add to the Raptors’ depth and identity as a defense-first team.

The great thing about a deal like this is it gives the Raptors three young prospects, any of whom could end up as a star. So it’s basically giving them three rolls of the dice.

SIAKAM TO KINGS

No deal with Sacramento would happen without them sending back either Haliburton or Fox, and I highly doubt they’d trade Fox. Haliburton would be a great addition to the Raptors with his ability to play and defend both guard positions, and he’s shown to have a high basketball IQ and a good, if awkward looking, 3 point shot. Bagley isn’t a bust yet and might blossom in a better setting. Hield could be moved to a contender looking for outside shooting.

This doesn’t have the same potential as the Golden State deal, but Haliburton is a proven commodity and Hield is a more valuable asset than Wiggins, due to a smaller contract (although he’s still overpaid).

SIAKAM TO CLIPPERS

Unless they’re trading Paul George, there’s absolutely not deal here, so the fact they’re “enamoured” with Siakam is as pointless as saying they’d like to also have Kevin Durant, LeBron James and Steph Curry on their team, as well.

I’m “enamoured” with owning an NBA team, but it should be as newsworthy as the Clippers being enamoured with Siakam.

SIAKAM TO BULLS

There’s been some discussion in some circles that the Bulls should trade for Siakam, whose career is more on the same timeline as Zach LaVine, Nikola Vučević ,and DeMar DeRozan than Patrick Williams. Most NBA analysts feel Williams will eventually turn into a good-to-great player, but he’s still a couple of years away from fully tapping into the potential, which is more along the Raptors timeline.

The downside is that because of salary purposes, a third team would need to be brought in for a sign-and-trade of Markkanen, so there would be a lot of moving parts. On the plus side, Williams is exactly the type of player Masai wants to fill his roster with and might be potentially the best player from any of the possible trades.

SUMMARY

While I mentioned Chris Boucher as possibly being traded, I haven’t included him in any possible trades. Why? Well, I’m not sure the Raptors could get enough back on his own. He’s a good defender, rebounder and three point shooter, but his extremely slight frame makes him better as a bench player. Because of that, any trade involving Boucher would probably include him in a larger package.

Furthermore, there’s no guarantee the Raptors will make any big trades before next summer. Even if Masai does decide trading Siakam is in the best interests of the team, if he isn’t happy with the deals he’s being offered, he’s not going to pull the trigger. Period.

The two things that will dictate what Masai and company do are their record and the development of Barnes. My guess is that if the Raptors are approaching the deadline around 20 wins or below (basically around or below .350), then I would expect Masai to make a similar adjustment to last year and try and make a trade. Otherwise, maybe don’t expect the fireworks.