When Patience Meets Purpose

The Case to Trade for Damian Lillard

Superstars, they’re essential to win but hard to come by.

There are 3 ways to acquire a superstar in the NBA. Either through the Draft, Free Agency or via Trade.

Almost a year ago, I made a video essay for Yahoo Sports Canada, that details how the Raptors were able to put themselves in a position to strike on a superstar deal while the iron is hot. 

That iron is currently burning up. 

The essay outlines the Raptors' patient approach to team building, emphasizing their stubborn reluctance to trade young players. It goes on to detail their conservative approach to free agency by avoiding contracts for older stars to maintain flexibility and their prudence in trading away future first-round picks. Their goal has always been to field a competitive team while safeguarding assets and financial flexibility. It’s why the Raptors are currently in the position they’re in, they’re asset-rich. 

With the summer nearing its end,  and the draft and free agency being things of the past, the trade market remains the final avenue for the Raptors to potentially land a superstar. But what goes into making a superstar trade?

Having the assets or a way to acquire them is 90% of the battle, the remaining 10% is the willingness to make that deal. 

The Raptors front office, in maintaining their flexibility, has also given the impression around the league that they are still not yet committed to picking a direction. In recent years the chatter around Ujiri has been that he overvalues his own talent often at the expense of making moves many consider fair to make. But those deals have consistently leaned towards a rebuild which would contradict, what the Raptors brass repeat ad nauseam - their desire to win.

A trade for Damian Lillard, however, is one that helps you win.

But it doesn’t come without risk. Damian Lillard reportedly does not want to be in Toronto. And while the Raptors have not shied away from disgruntled superstars in the past, that was a much different circumstance. 

The risk in the Kawhi Leonard deal was much lower. The DeMar DeRozan/Kyle Lowry pairing had reached their ceiling and after multiple chances and roster tweaks were nearing their end. 

Looking at where the Raptors stand today, I'd argue that Toronto risks more by not pursuing Lillard.

Let’s get into it. 

The Toronto Raptors are coming off a rough year that saw them finish 41-41 and lose to the Chicago Bulls at home in their lone play-in game, missing a franchise record 18 free throws leaving fans scarred with the lasting image of a 10-year-old screaming from the baseline. Then, in the offseason, things took a turn for the worse when they lost starting point guard Fred VanVleet to the Houston Rockets for nothing.

While they did manage to re-sign Jakob Poeltl to a 4-year deal, they head into the upcoming season with three of their core players Pascal Siakam, O.G. Anunoby, and Gary Trent Jr. all on expiring contracts.

Ideally, the Raptors lock these guys into contract extensions before the season and breathe a sigh of relief, but due to wrinkles in the CBA, O.G. and Siakam stand to gain more waiting for Free Agency.

The catch is if O.G. and Siakam hold off until Free Agency, the Raptors run the risk of losing even more talent for Zilch next offseason. That would make them the seventh and eighth players from the championship roster to bid Toronto farewell in Free Agency.

Outside of Kawhi Leonard, losing the first 5 guys from the championship team was the smart conservative approach to team building. Not offering Green, Gasol, Ibaka or Lowry contracts was done to prioritize future flexibility and their belief that the younger guys on the roster could carry the mantle. 

Over the course of 8 years, through the G-league and development of the bench mob, what the Raptors have in O.G. Anunoby and Pascal Siakam are players that represent the investment the team has made in their culture, roster, and overall development. In continually over-valuing his players Masai has signalled his belief in them. He doubled down on this belief, by bringing back his former #9 overall pick, Jakob Poeltl.

So this then begs the question, what is the bigger risk? Trading for a superstar who isn’t exactly thrilled about playing in Toronto, or risk facing Siakam and Anunoby’s final season with glaring roster holes, and no true path to the goal you’ve repeatedly set out for. 

There's a real threat that the Raptors might end the season without a playoff berth, no draft pick (traded to San Antonio the previous season for Jakob Poeltl), and the loss of Siakam and O.G. due to a stubborn reluctance to build a team around them.

This is why making a deal to build around this core is suddenly the prudent move.

Damian Lillard just so happens to be a perfect fit in Toronto. 

The loss of Fred VanVleet this summer meant losing not just their starting point guard but also their best ball handler and pull-up shooter.

With all due respect to FIBA MVP Dennis Schröder, he represents a step back from Fred VanVleet. Schröder thrives in an environment with ample spacing, while VanVleet, despite his struggles last season, was the team's spacing.

Fred VanVleet even in a tough shooting year managed to form a deadly Pick and Roll partnership with Jakob Poeltl. While VanVleet is a great shooter, Damian Lillard is one of the most elite shooters in NBA history. Lillard last season led the league in pull-up 3-point attempts at 7.4 a game, shooting 37.4% on them. With Lillard on the roster, Poeltl would regain a partner who just so happens to be one of the best pick-and-roll guards in the league. And for how dangerous the VanVleet Siakam two-man actions were, Damian Lillard would make those same situations a death trap for opposing defences. Off-ball, Lillard represents the closest comp to Steph Curry the league currently has, and for a spacing-starved Raptor team, his gravity would help open the floor for the Raptors’ bevvy of playmaking forwards. Given the obvious fit, it’s easy to see why the Raptors would want to make this work.

As for Damian Lillard, he’s a player who has waited years for Portland to pair him with a secondary ball handler. Toronto has that in droves with Siakam and Scottie Barnes, and any other combination of big wings Toronto can manage to keep in a potential Lillard deal. While Lillard’s Portland teams struggled to pair him with the defensive support he needed to achieve ultimate success in the playoffs, Toronto boasts some of the best defensive players Lillard would have ever played with.

So what would a deal for Lillard possibly look like?

Toronto trading for Dame straight up, in a two-team deal, doesn’t feel likely for a number of reasons.  

First, despite Portland’s interest in Scottie Barnes, it has been reported by many that the Raptors have zero interest in trading Barnes. A deal that includes him, would also require Toronto to give up much too much of their depth. 

The prospects of O.G. Anunoby or Gary Trent Jr. heading to Portland also appear slim.

It doesn’t seem very likely Portland is in the market for a scoring guard like Trent Jr., as they already have Anfernee Simons, Shaedon Sharpe and Scoot Henderson.  This is why many of the Miami HEAT trade proposals do not work, as they centre around Tyler Herro, who does not fill a need for the Trail Blazers.

Portland’s interest in O.G. doesn’t feel very strong to me, as they just gave Jerami Grant the max a month ago, and Anunoby would likely command a similar salary. It doesn't strike me as realistic that Joe Cronin and the Trail Blazers are planning to construct a team with two max-wing players, neither of whom are All-Stars.

Lastly, trading Pascal Siakam for Lillard is a non-starter in my view. The Raptors would only be adding Dame with the immediate goal of winning, and Pascal Siakam stands as the best player they have to achieve that.

So if a two-team trade is unlikely, what would three or four team trades look like?

As of Saturday, reports indicate that Phoenix and Indiana are both willing to help facilitate a Damian Lillard trade.

The Phoenix Suns as reported by Gerald Bourguet, have interest in a Deandre Ayton for Jusuf Nurkic swap, in which they can potentially turn Ayton’s salary into two rotation players to give them depth around their superstar trio.

The Suns are looking to compete against the Nuggets and want a big body to bang down low, they also want to shore up their defence.  While Nurkic may not be the perfect defender, his addition alongside O.G. Anunoby (who Raptor fans know has and can go up against Jokic) certainly gives Phoenix the defensive coverage they are looking for.

Framework (Picks ignored):

The Blazers receive the 2018 #1 overall pick Deandre Ayton, along with the 13th overall pick in the 2023 NBA draft, Gradey Dick. Deandre Ayton represents a young player on a long-term deal at a position of need for a young Blazers team filled with high-scoring guards. Of the available packages reported Ayton is likely the best returning piece in any Blazers deal. (Picks not included in framework). 

A key to remember is that given the Suns’ roster situation, they lack any meaningful salaries other than Ayton to trade, so this type of Ayton trade would require getting back a player that makes in the range of $15 - $19 million. That player in addition to Nurkic would need to be good enough for a win-now team to actually make it worth trading Ayton. 

Indiana is reportedly interested in trading Buddy Hield, a 30-year-old veteran who has an expiring contract worth just over $19 million. The Raptors are in dire need of shooting, and few in the league are better at that than Hield. It just so happens that O.G. Anunoby already has ties to Indiana, having attended college there, and the Pacers are frequently rumoured to have had their eyes on him.

It's not difficult to imagine a trade scenario involving Buddy Hield + picks for Anunoby. Picks, the Raptors could then redirect to Portland in a Lillard trade.

And given Portland's continued interest in an Ayton for Nurkic swap, the Raptors could replace O.G. Anunoby with Gary Trent Jr. in the previous trade proposal. However, in this scenario, additional draft picks or assets may be necessary to sweeten the offer, as Phoenix is likely to demand more than just Nurkic and Trent Jr. for Deandre Ayton.

Those are just a few of the several creative avenues the Raptors can explore to make a deal happen.  It seems that most of these scenarios involve moving O.G. Anunoby.

Considering Siakam's age and his readiness to win now, he is untouchable in a Lillard deal. On the other hand, due to his youth, Scottie Barnes represents the future of the Raptors. This is where O.G. Anunoby comes into play as the Goldilocks player in any potential trade.

It’s also the reason the Raptors should want to keep him, he fits on any timeline, and he fits like a glove on any roster. For example, Dame has never played with a perimeter defender the likes of Anunoby, his defence, shooting, and cutting make him the perfect addition to any lineup with Lillard. 

By keeping Scottie Barnes, the Raptors secure better long-term value. Looking four years ahead, when Dame is 37 and Siakam is 34, having a 26-year-old like Barnes to build around serves as insurance for the future, all while striving for immediate success— and isn’t that the promise the Raptors have been striving to fulfil?