Raptors didn’t get Damian Lillard, but rumors show status quo isn’t an option

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Let’s hope nobody out there got a Damian Lillard Raptors jersey custom made.

The Toronto Raptors were heavily rumoured to be attempting to trade for the Portland Trail Blazers legend, and they were indeed interested. To what extent, it is hard to say — not enough to beat out what the Milwaukee Bucks and Phoenix Suns could send to Portland to eventually pair Lillard with Giannis Antetokounmpo in Wisconsin.

For the Bucks, it is a trade that makes total sense. Antetokounmpo had begun to make noise about needing evidence of his team’s desire to compete at the highest level. Without Lillard, the Bucks still would have been a title contender. With him, their title odds improve. It is a win-now move for a team that has won a lot of games, but was under pressure to display the willingness to get the most out of Antetokounmpo’s prime.

As it happens, the Bucks won a league-high 58 games last year. The Raptors won 41. Not that it is ever an easy decision to give up a player as good as Jrue Holiday, another starter in Grayson Allen, as well as a future pick and two pick swaps. With one of the best players in the world in his prime and exerting a little bit of pressure, they had as much incentive as any team to pull off this sort of trade.

It was much more complicated for the Raptors. Reasonable minds could disagree on whether or not making a competitive offer would have been the right move. While some could have said that it would have been too high of a price to pay for a player who would not have turned them into a championship contender by himself, acquiring Lillard at least would have represented the Raptors picking a lane. For many fans, that would have been the main source of excitement, which isn’t to count out the possibility that those Raptors could have been a pretty good team. Mostly, it would have been new and fun, a stark contrast to last year’s maddening mediocrity.

That is moot now. What the Lillard rumours really clarified for the Raptors — at least, what they should have clarified — is that maintaining the status quo is becoming more and more dangerous by the day. Sure, not trading Pascal Siakam earlier in the offseason meant they were in a position to make a legitimate offer for Lillard and have it make some sense. As long as you have Siakam and one of O.G. Anunoby or Scottie Barnes, the addition of another high-end player could make the Raptors a legitimately interesting team in a still-uncertain Eastern Conference, even if Milwaukee solidified itself as at least the co-favourite by acquiring Lillard.

There is a ticking clock, though. Siakam and Gary Trent Jr. will both be unrestricted free agents at the end of this season and are extension eligible now. Anunoby has a player option he will certainly decline for 2024-25, and is also technically extension eligible, although the most money the Raptors can offer him is less than what his market value would be. In other words, he will become an unrestricted free agent next summer.

The Raptors could continue to stay patient, keeping themselves in a position even longer to take a win-now. Maybe Joel Embiid grows frustrated in Philadelphia sooner than anticipated. Maybe New Orleans wants to get off the Zion Williamson roller coaster, and the Raptors have an appetite to navigate that risk-reward conundrum. Luka Dončić’s relationship with the Mavericks could go haywire, as Kyrie Irving doesn’t have a history of stabilizing situations for the long term. Holiday, who just went from Milwaukee to Portland, would look good in Toronto, although he is not the offensive supernova Lillard is and can become a free agent this offseason.

That is the biggest problem for Toronto. The window to pull off a win-now move is closing for the Raptors. You probably cannot stop Anunoby from going to free agency, so the Raptors had better figure out what his priorities will be when that time comes — in a way that meshes with the anti-tampering language in the collective bargaining agreement, of course. Is that compatible on a team with both Siakam and future pillar Barnes? Is it compatible with just one of them? If not, you move him for as much as you can get, and as soon as possible.

If you want to keep that competitive window open, you are pretty much obliged to keep Siakam around. Even if he’s slightly over-extended as a top offensive option, he is a fabulous player, one of the 20 or 30 best in the league. If the Raptors want to continue trying to win, they need to offer him as much money as they can, immediately. On that end, the ball has been in the Raptors’ court for a while. If they no longer see a path to competing at a real level with Siakam, once again: move him for as much as possible, as soon as possible. The Raptors would have Bird rights on both Siakam and Anunoby, meaning they can surpass the salary cap and luxury tax in order to retain them. Making those, in addition to extending Barnes, would send the Raptors hurdling the luxury-tax threshold, a line teams not likely to win a round in the playoffs are hesitant to cross.

Barring the type of trade that just got done happening for the Raptors, this is going to become more about Barnes than Siakam at some point. That was the risk of holding on to all their veterans at last February’s trade deadline, as well as the risk of trading for and re-signing Jakob Poeltl. It is not that any of those moves (or non-moves) represented bad value plays in and of themselves. The offers for the Raptors veterans have not been overwhelming. But for a roster that seemed to scream out for medium- or long-term prioritization over short-term goals, the decisions did not coalesce with the Raptors’ most valuable piece when thinking about how roster building works in this league, even if Barnes is not yet the Raptors’ most valuable player on the court.

Now, the past is irrelevant. The Raptors have been beyond patient trying to make this work. It played a part in costing them Fred VanVleet in free agency. With the Kawhi Leonard acquisition in 2018, Masai Ujiri made the perfect trade. More often than not, though, perfect ends up being the enemy of good. Keep trying for the former, you might end up with considerably less than the latter.

(Photo: Steph Chambers / Getty Images)

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