No Lillard, no problem? For the Raptors, that remains to be seen

Portland Trail Blazers guard Damian Lillard (0) dribbles the ball as Toronto Raptors forward Pascal Siakam (43) defends during first half NBA basketball action in Toronto on Sunday, Jan. 8, 2023. (Frank Gunn/CP)

The biggest question looming over the Toronto Raptors with training camp approaching has been answered. 

Despite sincere interest from Toronto, who even had growing optimism that they could make a late push and secure Portland Trail Blazers superstar Damian Lillard in a trade, the dynamic guard will instead be taking his talents to the western shores of Lake Michigan to try and run the Eastern Conference alongside Giannis Antetokounmpo and the Milwaukee Bucks. 

For a brief moment, there seemed the possibility that the Raptors would be going pretty deep into their future asset base — think as many as three first-round picks, two pick swaps and rookie forward Gradey Dick — to acquire Lillard, a 33-year-old guard who can single-handedly ignite an offence and also has four years and $216 million left on his contract. 

Per one Western Conference source, it’s believed the Raptors were hoping to construct a deal that would not include their core pieces — Pascal Siakam, O.G. Anunoby or Scottie Barnes

Maybe that was a sticking point, but you can see what Toronto might have been thinking: Lillard on top of their existing talent could work in an uneven Eastern Conference.

Lillard in place of it? Not so much. 

Regardless, by Wednesday morning the feeling was the moment had passed, with insiders predicting that Miami — Lillard’s preferred destination all along — would end up pushing a deal over the line. 

Instead, it was Milwaukee — the NBA’s anti-Miami — who surprised many league insiders as the Bucks pulled out the stops to appease Antetokounmpo who has been vocal about the team proving their commitment to gunning for championships while he’s still in his prime and under contract to Milwaukee. A not even slightly veiled threat that he would force his way out of the small market if he perceived the organization’s zeal to win another title didn’t match his own. 

In the end, it was some cold business, as acquiring Lillard meant sending Jrue Holiday – a much-loved and respected foundational piece of the 2022 title team – to Portland without so much as a farewell dinner. 

“It’s self-preservation,” was how one rival executive described it. “You either have to appease Giannis or he leaves, and you get fired.”

Was the deal constructed the best Portland could do? 

The Trail Blazers get the right to swap picks first-round picks with the Bucks in 2028 and 2030 and Milwaukee’s unprotected first in 2030. They are also expected to explore options for moving Holliday, with the asking price expected to be two more future firsts.

They also get 25-year-old former No. 1 overall pick DeAndre Ayton from Phoenix as part of the three-time trade that saw the Suns add Josef Nurkic, Nassir Little and Keon Johnson from Portland and Grayson Allen from Milwaukee to bolster their bench. 

For what it’s worth, it seems unlikely that the Raptors would shift their gaze to Holiday, as quality a player as he is. The lure of Lillard was instant spacing to benefit Barnes and Siakam. Holiday is a quality player and elite defender, but adding another so-so perimeter shooter to a lineup heavy with them doesn’t seem like a direction the Raptors are in a hurry to head. 

So, from the Raptors’ point of view, it makes it more certain than not that the team that takes the floor for rookie head coach Darko Rajakovic will emerge from the roster that takes the floor for the first day of training camp in Burnaby, B.C. on Tuesday. 

Our regular pre-season programming can resume as planned. 

And guess what, this team still has some questions. 

Will Scottie Barnes emerge as a star in his third year, the kind of player that justifies him being a player the Raptors refused to include in hypothetical deals for Kevin Durant and Lillard in consecutive summers? 

Will the Raptors be able to retain O.G. Anunoby in free agency next summer? One of the reasons he figured prominently in the trade speculation regarding Lillard is that it’s widely presumed that what the Raptors can offer him in a contract extension – about $117 million over four years – will be dwarfed by what he can get in free agency. If the Raptors do have to pay Anunoby something significantly more, will they also be able to afford to have Pascal Siakam on a max deal (his extension would be in the range of $200 million over four years) and Barnes on a max extension on his rookie deal? 

It’s a lot of money that could be tied up in a trio that doesn’t have a track record of post-season success. 

And now that the Lillard noise has settled down, attention can be turned to Siakam, the Raptors’ best-returning player and one who seemed destined to be traded in the summer, with Atlanta as perhaps the most likely destination. 

That talk eventually cooled, but the level of commitment Toronto has to the two-time all-NBA player is still uncertain. There have been no talks on a contract extension, per sources, with the team seemingly taking a wait-and-see approach to get a sense of how the existing pieces – Siakam primary among them – fit within whatever offensive system Rajakovic chooses to employ. 

There are plenty of questions around this team, as the Raptors are, after all, a team that has been in the draft lottery, lost in the first round of the playoffs and then in the first round of the play-in tournament over the past three seasons.

The year before that they had the second-best regular season record in the NBA and the year before that a championship. 

There have been a lot of changes in a short period of time, but exactly what it all adds up to remains a pressing concern. 

They’re not in the process of accumulating as many future assets as possible in the form of draft picks and young prospects, or they don’t seem to want to be, based on the team’s decision to trade a first-round pick for veteran centre Jakob Poeltl at the trade deadline last year and its pursuit of Lillard. 

And the Raptors are not a team that, as constructed, projects as a contender. 

Is the plan to grow and be patient? Is it to wait until the next superstar becomes available and try and get them on the cheap again? 

Those are questions we can’t answer for now. But with the Lillard saga resolved the Raptors still have plenty of questions as they head into an uncertain future.

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