Would adding Damian Lillard make the Raptors a championship contender?

Damian Lillard is a megastar, and the Raptors have succeeded trading for one before. This time?

I remember the first time I put honey in a dish. I was working on a soy sauce pork chop dish (I didn’t really google or know or use recipes back then), and it didn’t taste wonderful. It needed to be sweeter. So the next time I made it, I saw honey in my pantry, so I used it. It was perfection, but it wasn’t simply sweeter. Everything tasted better, the meat richer, the sauce more balanced. Even the Kraft Dinner on the side tasted better. One new ingredient can alter how all the others manifest.

That’s what Damian Lillard could do for the Toronto Raptors. Of course, my honey had no autonomy whatsoever, let alone expressly negative feelings for joining the soy sauce. Lillard of course has made it known he doesn’t want to join the Raptors. But Toronto has a history of swooping in to trade for disgruntled superstars (who also publicly made the Raptors aware he didn’t want to join them), and Lillard would be the new ingredient that would alter how all the others manifest. 

But would Lillard’s addition be enough for the Raptors to be a championship contender? First, let’s define what the Raptors would be like with Damian Lillard. Then we’ll move to what constitutes a championship contender. And then we’ll end with plausibility and possible trades and the resulting team. So, stick with me here.

Lillard would reforge the Raptors anew in the fires of his offensive genius. Or, you know, something less fantasy-y but still just as impactful. He’d fill a Lillard-sized hole in Toronto’s roster. He’d lead Toronto to the playoffs and then dominate once there; he’s one of the most clutch players in the league, with the most made shots in the NBA (25) since entering the league to tie or take the lead within the last 10 seconds of a playoff or regular season game.

Most of all, the Raptors right now need shooting — both off the bounce and the catch. Lillard would provide.

No team had a worse eFG percentage than Toronto in both catch-and-shoot and pull-up 3-point ranks. Lillard, on the other hand, took the highest rate of pull-up triples in the league last year and was absurdly successful at them. His eFG percentage on pull-up triples was 56.07. (Toronto’s eFG percentage on all shots last year was 51.7, 28th in the league.) Even more impressive, Lillard did so while taking some of the most difficult pull-up jumpers in the league, with an expected eFG percentage of 44.56. His improvement of more than 10 percentage points on such shots ranked third in the league among the 29 players with at least 200 pull-up triples last season.

And Lillard’s ability to drain pull-up jumpers would shift the entire defense towards him during Toronto’s pick and rolls, pulling everything a foot further away from the paint, and opening more catch-and-shoot jumpers for his teammates. To that point, among 61 players who ran at least 1000 pick and rolls last year, Lillard finished with the second-highest points per chance. And Toronto’s three main catch-and-shoot gunners last season, O.G. Anunoby, Gary Trent jr., and Fred VanVleet all had below-average shot quality on their catch-and-shoot triples. With Lillard’s defense-warping shooting above the break, Anunoby and Trent would find much easier jumpers off the catch. 

Lillard’s being on the court simply solves a team’s shooting problems on his own. Last season, in 1765 possessions with Lillard on the court and Anfernee Simons off of it (Portland’s second-best shooter), Portland shot 38.3 percent from deep. With Simons and Jerami Grant off the court (Portland’s third-best shooter last season, arguably), Portland shot 39.1 percent from deep in 738 possessions. Portland virtually never lacked shooting as long as Lillard was on the court. On the other hand, Toronto’s lineups with all three of the team’s best shooters in VanVleet, Trent, and Anunoby shot just 36.2 percent from deep last year.

Lillard was the most efficient isolation player in the NBA last year among those who isolated at least 250 times, per Second Spectrum. He is virtually as efficient shooting 30-footers as the Raptors as a whole were at 24-footers.  

His shooting alone would improve Toronto’s offense by leaps and bounds. If you simply replaced 658 of Toronto’s triples last year, shot at the team’s average rate of 33.5 percent, with Lillard’s 658 triples shot at his 37.1 percent, Toronto would have added approximately 70 or 71 points to its season. Slightly under a point a game was the approximate difference between Toronto’s 41-41 season last year and the Phoenix Suns’ 45-37 record. It’s a big deal! And that’s without including the cascading effects of extra space for other shooters, warped defenses for drivers, and bigs further away from the rim in pick and rolls. 

The shooting would statistically vault Toronto from a poor offense to an above-average one. Fortunately for his next employer, Lillard is far, far more than just a shooter. 

Lillard is also one of the best finishers in the league at the point guard spot. And Toronto has also lacked rim pressure from the guard positions ever since Kyle Lowry left the franchise. Lillard shot 63 percent at the rim last year and 47 percent from the short midrange, but great numbers for a point guard. He reached the rim at an elite rate. VanVleet, as a point of comparison, reached the rim far less and shot almost 10 percentage points worse from each area. Lillard may not be a highflying dunker anymore, but his finishing when opponents overplay his shooting is an elite weapon.

His frequency and efficiency on shots out of drives were both brilliant, scoring more than 1.3 points per chance on more than 9 shots out of drives per 100 possessions, per Second Spectrum. No Raptor last year came close to those numbers, with Siakam’s 6 shots out of drives and 1.1 points per chance leading the team. In fact, the only players in Second Spectrum history (starting in 2013-14) to record at least 9 shots out of drives per 100 possessions and at least 1.3 points per chance on those shots are Lillard, Luka Doncic, James Harden, and DeMar DeRozan.

And the cascading effects of Lillard running Toronto’s offense would be virtually limitless. Lillard received the seventh-most double teams per game last year, ahead of both Siakam and VanVleet (each of whom ranked in the top 20). He is an elite organizer of the half-court, creating advantages simply by existing with the ball in his hands. Siakam would see his touches decrease while enjoying a far higher quality per touch. He’d see dramatically fewer double teams and far fewer bodies in the lane on his drives. His efficiency would likely skyrocket. 

There are yet more advantages to Lillard on the offensive end. He’d be the best passer on the Raptors since Kyle Lowry, and though VanVleet made huge strides last year, Lillard is a cut above. And his best passing trait is his skip pass, allowing him to whir the ball from far above the arc to the corners in moments, manipulating the defensive attention paid to him as a result of his 30-foot shooting prowess.

For years, Portland’s greatest offensive weakness has been a lack of a second option who could attack a rotating defense and capitalize on the outrageous advantages created by Lillard. Their best player at doing so in the entirety of Lillard’s career has arguably been CJ McCollum, or perhaps LaMarcus Aldridge. Siakam is a significantly better driver, with a higher points per chance on drives in his career than either, according to Second Spectrum. Siakam would likely be the best offensive player alongside whom Lillard has ever played, and the two would be a complementary duo. A Lillard-Jakob Poeltl pick and roll, with Siakam positioned as a second-side attacker, and perhaps Anunoby and Trent spacing the floor, would be one of the NBA’s best offensive setups.  

Picture that play but with Siakam attacking the two-on-one advantage, and Anunoby in the corner as the shooter. That will score 2 or 3 points on a huge portion of such events. 

Or, on the other hand, picture this play but with Lillard creating the advantages for Toronto. The Raptors would create far more advantages at the point of attack and see Siakam catching with the defender rotating, rather than already in his grill.

It’s not hard to imagine Toronto’s offense skyrocketing to a top-10 unit with Lillard in place. Last year, Lillard had the single highest offensive EPM in the league, above even Nikola Jokic. He is a megastar, and he would join a Raptors squad that sorely lacks the skills Lillard would provide while at the same time offering in spades the ideal complementary skills that Lillard’s teammates have long lacked. The fit is perfect.

If the Raptors start to succeed in the half court, then their gamification of possessions becomes a value add rather than the whole boat. Last season, Toronto scored 94.5 points per 100 halfcourt first shots (not including offensive rebounds) while allowing 98.5 on defense. In other words, they started every game down approximately 3 points (there aren’t 100 halfcourt possessions in a game) based on their poor shooting, advantage creation, and rim pressure. Lillard would change all of that, meaning Toronto would start every game up points rather than down due to halfcourt prowess. If you sort every season of every player since 2013-14 in Second Spectrum and look at the efficiency of an average half-court touch (among players with a minimum of 1000 touches in a season), Lillard’s half-court touches last season were worth on average 1.085 points per first shot — ranking in the 99th percentile of the list. 

Lillard projects to fix everything that is wrong with Toronto.

When is an ice pick more dangerous, when you’re hanging on the cliff edge with it for dear life, or when you’re on solid ground and wielding it as a weapon? Or, put another way, whipped cream isn’t a meaningful meal, but it can add a lot on a finished dessert. 

Toronto’s possession-based focus may not maintain under a new head coach, but the team still has a plethora of players who both crash the offensive glass and force turnovers to start transition possessions. If the team is already scoring well in the half court, and stopping opponents from scoring the other direction, then running in transition and crashing the glass would be back-breaking. 

Furthermore, it’s very hard to imagine Toronto’s defense sinking below a top-10 unit with Siakam, Anunoby, and Poeltl in place. Lillard has never been an elite defender, but neither has he had an elite defensive infrastructure in place to support him. Toronto has the switchable wings, rim protection, size, versatility, and mind-meld chemistry in place (if last season was a blip) to support a player who may not create elite defensive moments on his own. Last year, lineups with all three of Poeltl, Anunoby, and Siakam were in the 80th percentile on the defensive end, and that remained true with or without VanVleet, Trent, or whomever else. A lineup with those three in it will defend well.

Is that a championship contender?

My instinct is to say yes. Here is a list of teams over the past five years that have finished within the top 10 on both the offensive and defensive end, as well as where they finished in the playoffs. 

Finishing the top 10 in both offense and defense certainly doesn’t guarantee you a shot at the championship, but the two traits do correlate. Of the 10 finals teams over the last five years, seven finished in the top 10 in both offense and defense. Lillard would be the best guard in the East, and Siakam would arguably be the best second fiddle in the East. It’s not hard to convince yourself that that team would reach the Finals.  

But that is if everything goes perfectly. There are many potential pitfalls between the date of pulling the potential trade trigger and that would-be series. There are so, so many what-ifs and unknowns in regards to Lillard joining the Raptors. Lillard is 33 years old, and health is never guaranteed. Beyond that, would he even suit up for the team? It’s unknown, but he’s under contract until at least 2025-26, with a player option for 2026-27. If he refuses to play, he wouldn’t get paid the much more than $100 million he is owed over those years, so it’s hard to see him not playing at all. 

But could the Raptors keep Siakam and Anunoby on the team while also trading for Lillard? In that case, the package would have to be centered around Scottie Barnes — who should be the exact type of player Portland currently wants given his limitless potential. But Anunoby is currently a better player, a better shooter, and better defender, and it’s hard to imagine Toronto having a strong enough team to support Lillard if it loses either Siakam or Anunoby. 

To make the money work, Toronto would need to trade a huge number of players alongside Barnes to match Lillard’s gargantuan salary. In addition to Barnes, Toronto could include, say, Chris Boucher, Thad Young, Otto Porter jr., Precious Achiuwa, and Malachi Flynn — that would match salaries. Would Toronto be deep enough after such a trade? Hard to say. The starters would be great, at the very least. 

Would the Blazers even accept such a trade? Again, hard to say. Barnes is far and away a more valuable piece than anything the Miami Heat could muster. But it would simply be guessing on my part as to whether Portland would accept such a trade, even with potentially a pick or two thrown in. 

Another what-if: What do the Raptors do if the trade is made for Lillard to fill out the roster? The last time around, Toronto made a further trade for a defensive-genius, shooting and playmaking center. If the Raptors trade for Lillard, the team would need to add several bodies just to fill out the roster, let alone to become a contender. Buddy Hield is available on the trade market, and I value him as a near-perfect role player. He’s one of the best shooters in the league (perhaps just below Steph Curry and Lillard), and he’s grown his game significantly as a secondary creator, cutter, and passer in Indiana. If Toronto goes for the gold, adding Hield would be a wonderful addition. Jaylen Nowell remains a free agent, and I’ve opined about wanting him as a Raptor previously. If Toronto no longer cares about the luxury tax and needs to fill roster spots, it would be mismanagement to not offer him a contract. Perhaps the Raptors bring Rudy Gay or Terrence Ross home. Let’s just assume all that happens (not that the 13th-15th roster spots should factor in, but just so we have names to put down), this is what the depth chart would look like:

PG: Damian Lillard, Dennis Schroder

SG: Gary Trent jr. (Buddy Hield?), Jaylen Nowell

SF: O.G. Anunoby, Gradey Dick, Terrence Ross

PF: Pascal Siakam, Jalen McDaniels, Rudy Gay

C: Jakob Poeltl, Christian Koloko

There’s not a huge amount of depth there, but it’s much easier for bench players to fit in when the top end is established and playing together. (Toronto proved the inverse of that this season.) And there’s some talent there. Schroder is a proven bench guard. Beyond that, Toronto’s 7-10 spots would be risks. Perhaps Dick pops as a cutter and shooter on a winning team. Koloko won his minutes last season come hell or high water, and he could be very successful in a defined role. The rotation could be feasible, but it would be a narrow path to paydirt. (Hield would really, really be the straw to stir the drink. If Toronto could somehow trade for Lillard and flip Trent for Hield, they’d truly have a stew going.)

I argued in the middle of the summer that Toronto simply needed to do something. Trading for Lillard would certainly be picking a lane. It worked for Toronto before when it dealt DeMar DeRozan and Jakob Poeltl for Kawhi Leonard. 

But the team that made that trade had just won 59 freaking games. This Raptors team is coming off a miserable 41-41 season. Toronto entering 2023-24 is in a very, very different place as a franchise than it was entering 2018-19. That adds dramatically to the risk. For one, there’s no longer the same institutional knowledge to carry the day. And if Lillard isn’t enough to push Toronto to the championship circle, or if anything else goes wrong, the Raptors would have virtually no means of recovering for several years. It would be trading away its future in Barnes (and, potentially, Achiuwa!). It would have few or almost none of its own high-value draft picks going forward to rebuild. And Lillard is aging and expensive. There are enormous risks that, if suffered, could drive Toronto into the basement of the league for years on end, with very few ways out. 

But the potential reward would be far higher than anything this group could currently accomplish. If Toronto manages to trade for Lillard, and if it manages to keep Siakam and Anunoby, and if Lillard reports to camp, and if the team gels, and if the team stays healthy, and if the depth pieces manage to fill defined roles, well, then you could be looking at a championship contender. How many ifs would you be willing to tolerate? How many do you think Masai Ujiri and Bobby Webster would bet on? Because if they do bet on Lillard, and the bet fails, it could theoretically mean the end of their tenure in Toronto. Toronto is facing a crossroads with glory and disaster both down one path, and something, who knows what, down the other. Only time will tell which path the Raptors will walk — and we may never know which would have been correct in the end.