Damian Lillard made his request to leave the Portland Trail Blazers on July 1, and until the last few days, it appeared the seven-time all-NBA point guard was destined for the Miami Heat. However, a handful of other teams have now thrown their names into the Lillard rumor ring, from the Milwaukee Bucks to the Chicago Bulls.
Perhaps no other franchise, though, has a better chance of actually completing a Lillard trade than the Toronto Raptors.
Raps’ President Masai Ujiri pulled a similar stunt with Kawhi Leonard in 2018, taking a massive risk on acquiring a superstar who didn’t want to play north of the border, but he did it anyway and the move paid of handsomely in the form of a 2019 NBA Championship.
According to NBA insider Marc Stein, Toronto’s interest – regardless of what Lillard and his camp may state publicly – is “genuine.”
Stein wrote on his substack (subscription required), “The Toronto Raptors have convinced numerous teams around the league that their interest in trading for Lillard is genuine.”
Stein adds, though, that the Raptors are reluctant to make an all-in push to acquire a player who doesn’t want to be in Toronto, and that the situation is different from that of Leonard’s, as Dame is under contract for the next four years and could make things miserable for Ujiri, if he so chooses.
It also seems, though, like Portland has frozen the Heat out of any trade talks, which takes a massive Lillard trade option off the table. If Toronto truly does hold interest and could decide to make a move for the 33-year-old, what might a deal look like?
Well, the trades would look fairly similar – Gradey Dick, the 13th overall pick in June’s draft; three or four future first-round picks; salary filler; and perhaps another young player, such as Precious Achiuwa.
There would be one significant difference in each deal, though, and that would be the centerpiece of the trade. The are a trio of Raptors’ players who could be that centerpiece, but who are they and what other assets could fill out an agreement between the two teams?
Toronto Raptors Damian Lillard trade centerpiece No. 1: Pascal Siakam
A deal built around Siakam would be the most unattractive for the Blazers. Though he’s twice been an all-NBA forward whose two-way game would be a perfect fit with Scoot Henderson, Anfernee Simons and Shaedon Sharpe, he’s also on a $37.8 million expiring contract.
That raises two questions:
- Would Siakam consider re-signing in Portland?
- Would Portland want to re-sign Siakam to a max (or near max) deal when they just shelled out $160 million over five years for a Siakam-lite in Jerami Grant?
Then there’s the question of whether or not it’s worth the Raptors sending Siakam away if they’re trading for Lillard, as making such a move would be to go all-in and win a championship. Why would they trade their best current player if the goal is to win now?
For what it’s worth, if Toronto did trade Siakam to Portland, it would be much easier to match salaries. With Siakam’s deal only about $8 million less than Lillard’s, cobbling together another contract or two to make a trade work would be simple.
Toronto Raptors Damian Lillard trade centerpiece No. 2: OG Anunoby
Parts of a potential Anunoby deal are similar to the issues that would accompany a Siakam trade.
Anunoby is 26 years old while Siakam is 29, so he fits Portland’s young-roster timeline, but he’s also an established NBA player. OG is an all-defensive caliber wing who’s quick enough and strong enough to guard 2 through 4 and he’s become a solid shooter from three, connecting on nearly 39 percent of his 5.5 threes a game last year.
However, is there room for Anunoby to grow as a player? If the answer’s yes, it’s probably not much. He could become a better scorer with increased opportunity, but will he get that with the Blazers alongside Scoot, Simons and Sharpe?
The former Indiana Hoosier is also a free agent next season (assuming he declines a $20 million player option) who will command a pretty penny on the open market, which begs a similar question to Siakam: Does Portland want to shell out the money to keep him?
The trade itself would be more complicated as well, as Anunoby’s salary is about half of Siakam’s. That means, along with Dick and a few picks, expiring contracts such as Otto Porter Jr.’s and Thaddeus Young’s would need to be included, and likely Gary Trent Jr.’s expiring $18.6 million deal.
How much are expiring deals worth to the Blazers? And what happens if Anunoby leaves?
Toronto Raptors Damian Lillard trade centerpiece No. 3: Scottie Barnes
Here’s where things get interesting. If Portland can talk Ujiri into parting with the 2021-22 Rookie of the Year in Barnes, the deal might be signed, sealed and delivered to the league tomorrow.
But the likelihood of Barnes being included in any Lillard deal is miniscule, at best. The Raptors weren’t willing to part with him in a potential Kevin Durant trade; why would they do it for Dame?
One argument would be that Barnes didn’t show much improvement last year after his rookie campaign. He showed the same flaws he did his first year in the NBA – he’s not a shooter or scorer, and that caused problems for Toronto offensively. Barnes is a fantastic passer and playmaker, and he’s a versatile defensive menace who will likely rack up all-NBA defensive team appearances during his career.
If he’s that limited on offense, though, can he be the best player on a championship team?
That would certainly be worth finding out for the Blazers. Plus, Barnes’ lack of scoring and shooting prowess wouldn’t be as much of an issue in Portland, which has better individual offense players than Toronto did last season.
The question is, would the Raptors be willing to part with someone they view as a potential franchise centerpiece? It would keep the team’s veteran core intact for a chance to win immediately – Dame would be joining Siakam, Anunoby and Jakob Poeltl – but is it worth losing Barnes and what he could become?
It feels like the more teams that join the Lillard rumors, the farther away a deal is from being completed. Toronto appears to be Miami’s biggest threat, and if there is no Miami from Portland’s perspective, then the Raptors become the most likely landing spot for Dame – at least for the moment.
But it doesn’t seem like there’s a perfect fit between Toronto and the Trail Blazers, either.