Is it Dame Time in Toronto? The latest on the Lillard sweepstakes

The talk of the NBA offseason has definitely been Damian Lillard’s trade request from the Portland Trailblazers. After several mediocre seasons in Portland, the team seems to be heading in the direction of full rebuild. Despite remaining loyal to the Trail Blazers for years (perhaps even longer than most would have), All-Star Damian Lillard decided enough was enough — he’d like to be shipped off to a contending team.

That was earlier in the offseason — now, with about a week left until most NBA teams kick off training camp ahead of the 2023-24 season, Dame has yet to be moved. When reports first came out of Lillard’s request to be traded, he had one destination in mind, the Miami Heat. Still, the Trail Blazers are taking their time — technically they don’t HAVE to listen to Lillard and could trade him wherever they want. Of course, with a star of his caliber, they want to get as much back for him as possible.

So, the rumour mill went wild. Of course, when someone of Lillard’s status is on the trade market, most teams are going to pick up the phone and see what the price is — as they should. Teams like New York, Chicago, and yes, Toronto came forward as potentials to be a part of the historic trade sweepstakes for Damian Lillard. As of Monday morning, even Boston is a large contender for Lillard.

Weeks after the trade request and subsequent news that Lillard's top (and only) choice as far as destination was Miami, MORE news came out. Apparently, Dame has made it known that if the Trail Blazers were to send him anywhere but Miami, he’d refuse to report to training camp. Truth or trying to gain back some control of his situation? Maybe a little of both.

Still, nothing happened. Every few weeks during the offseason, the news cycle would return to Damian Lillard and his desire to be dealt to the Heat. Apparently Portland did not like Miami’s offer. The other teams in contention were brought up, and the cycle continued...

Yet now, it’s crunch time — or Dame Time, as some may say. There are about seven more days until NBA players will be heading to training camp. Lillard is surely no about to report to Portland Trail Blazers training camp, and they still haven’t managed to trade him. It makes sense that they’d like to get a deal done so that they can get whoever they get in return to report to camp. Sure, it’s not ESSENTIAL they make a deal in the next seven days, but it sure seems to be the most logical route for a team looking to continue their rebuild.

It seems Masai Ujiri pulled out of talks with Portland last week but is back in... strategy, or is Toronto legitimately playing the game for Damian Lillard?

The talks have seemed to increase over the past several days. Let’s see where Toronto stands in the race for Damian Lillard:

The Raptors seem to have genuine interest

In the latest report from Marc Stein, it seems the Toronto Raptors have “convinced teams around the league that they have genuine interest in trading for Dame.” It makes sense — think about the last time the Raptors traded for a star. It was 2018, the team seemed to be at a plateau, Kawhi wanted out of San Antonio, and the price was right. He comes to Toronto, wins a championship, fun times all around.

Now, this time isn’t really the same. Back in 2018, Kawhi only had one year left on his contract. Sure, it was reported that he did NOT want to come to Toronto, as it has been reported with Dame — BUT he realized his chances of winning it all, and sucked it up for a year. It was worth it.

Dame has four years left on his contract. Plus, if the price for Dame really is that high, do the Raptors even currently have the assets to trade for Lillard while still retaining a good enough supporting cast to make a real run? That 2018-19 team was not JUST Kawhi Leonard — you had Lowry, Siakam, Ibaka, Gasol, that bench squad etc.

Plus, Dame is 33 years old. Now that doesn’t have as much grounds for concern in 2023 as it may have ten years ago — sports medicine has advanced so far that players don’t have as many problems playing into their late thirties. Steph is still playing at high levels, LeBron — even WNBA star Sue Bird was still playing top-notch basketball before she retired at 41 years old last year. Still, the concern is there to mortgage your entire team for a 33-year-old guard.

Toronto would have to send a fair chunk of their current roster away to get Dame from Portland — would the remnants be enough to build a contending team? Is Dame himself enough to launch the Raptors back into the championship stratosphere?

Damian Lillard (allegedly) has no interest in coming to Toronto

Reports this weekend further strengthened the stance that Lillard does NOT want to go anywhere but Miami. As Toronto seems to become more and more of a contender to get Dame, more and more talk comes out that he would refuse to show up if he were traded to the Raptors.

One source went so far as to say that Damian Lillard would “make it ugly” if he were to be dealt to Toronto.

Apparently, Toronto is his least desired landing place, as he we haven’t gotten reports of him “making it ugly” if he ended up in Chicago or anywhere else.

Yet, again I bring it back to Kawhi Leonard, who said the same things. I know, I know, it’s different — the contracts are different, the current roster is different, Dame and Kawhi are different. Yet, would Dame go so far as to “make it ugly”? I guess the only way to find out is to see it happen.

Does Toronto have the assets?

Any trade for Damian Lillard is going to be pricey. If Toronto were to be part of a simple one-on-one trade for Lillard, do they have enough assets to even be considered? Would it be worth it?

You’d have to send at least a few starting-caliber players — think about who the Raptors have right now. Siakam, Barnes, Poeltl, Trent Jr., Schroder, Anunoby (as far as starters), plus a few bench players who could be thrown into the mix in a trade.

Would Portland want Trent Jr. back a few years after trading him, especially in a contract year? Then there is Anunoby — but is he enough to persuade Portland to hand over Dame? You could add Siakam or Barnes — but then where does that leave Toronto? Dame himself can’t win a championship alone. If you deal multiple of Toronto’s best players just for Dame, you’re left in the same spot the Raptors are now — good but not great enough to make a real run.

The best situation for the Raptors right now seems to be a multi-team trade. The Raptors could get Dame, Portland could get the assets they want, and the Raptors would not have to clear their entire roster.

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Time seems to be ticking down to the wire as it pertains to Damian Lillard’s future in the NBA. Which city will be on Dame Time this season? The answers may be coming sooner than we think...