Raptors are in the mix for Damian Lillard. But is it a good idea?

TORONTO – The Toronto Raptors are back.

Not officially, mind you. That doesn’t happen until next Monday, when NBA training camps officially open, but the OVO Athletic Centre has been a hub of activity for a couple of weeks now, with all present and accounted for save for incoming point guard Dennis Schroder, who was busy through the second week of September helping Germany win the FIBA Basketball World Cup in Manila.

An excused absence, in other words.

But the real question — and an unusual one on the cusp of the pre-season — is who will be in the gym when the team has its first official practice in Burnaby, B.C., on Oct. 3.

On that front, you may have heard that the Portland Trail Blazers are planning to trade superstar point guard Damian Lillard.

And yes, I can confirm the Toronto Raptors, per sources, are very much in the mix. Certainly not all the way there and likely not even halfway to getting a deal done, but progress has been made.

Now, you may have heard this kind of thing before. A big name on the trade market, Raptors skulking around, trying to swoop in and steal everyone’s thunder.

Just over a year ago, Kevin Durant was the Hall of Famer looking for a new address, hoping to escape the fiasco that was Kyrie Irving and the Brooklyn Nets.

The Raptors were the dark-horse team then, confident that given the current of the marketplace, they could slide in and win the bidding with their collection of future draft picks and roster players not named Scottie Barnes.

It never happened: The Nets pulled Durant off the market, very publicly before the season started, and Durant was traded to Phoenix — his preferred destination all along — for a fairly healthy return centred on budding star Mikal Bridges and a slew of picks.

Long before that — we’re talking the COVID-shortened off-season of 2021 — the Raptors were keeping their powder and cap sheet clean in order to make a run at Giannis Antetokounmpo if the Bucks star chose to test free agency.

Again, it never happened — Antetokounmpo signed an extension and led the Bucks to a title in 2022 — though, interestingly, the two-time MVP has lately been very loud in musing his time in Milwaukee may be coming to an end sooner than later.

Still, the Raptors did once come from the outside lane to make a deal for a superstar in Kawhi Leonard, and it led to a championship. For that reason alone, Toronto’s interest needs to be taken seriously. The Raptors have a track record.

So, with the season just around the corner, there are two relevant questions for the Raptors to consider. How interested they are in making a deal for a 33-year-old point guard with four years and $216 million remaining on his contract? And, should they be?

From what I’ve gathered, the answer to the first seems to be that they are very interested. As a team that has struggled with spacing, shooting and half-court offence in general, the addition of Lillard — a top-five offence unto himself and arguably the NBA’s most dangerous shooter other than Steph Curry — would solve a lot of problems.

Sure, you have to overlook that Lillard is a defensive liability, has an injury history and has lifted Portland past 50 wins or the first round of the playoffs once in the past seven seasons. But coming off a season in which he averaged 32.2 points with a True Shooting percentage of 64.5 — both career highs — there’s no question that Lillard’s function as an on-court magnet would open up space for everyone else.

Can the Raptors get a deal done? We’ll find out soon enough.

One league executive I spoke with over the weekend believed that if the Trail Blazers are going to move their iconic guard as part of their rebuild, it will happen early this week, otherwise the urgency may pass and they might wait until the trade deadline and the market gets frothier, as the Nets did with Durant.

By all accounts, the Raptors seem at least reasonably confident they can manoeuvre their way to the front of the line, past the Miami Heat — Lillard’s preferred destination — and ahead of a team such as the Nets, who have the draft picks to get something done if Portland is open to taking on the last two years of Ben Simmons’ contract. The Orlando Magic could also make themselves heard, per sources.

For Toronto to be in the mix, it would require it to lift the top-six protections on the 2024 first-round pick it owes San Antonio to finish off the Jakob Poeltl trade from last season. That done, the Raptors could throw their 2026, 2028 and 2030 first-round picks into a deal, and some pick swaps too.

As for the players the Raptors can or will put in a deal?

By process of elimination, it probably would come down to a deal built around O.G. Anunoby, who — at age 25 — best fits the Trail Blazers' youth-oriented timeline. He provides elite perimeter defensive skills and high-end catch-and-shoot credentials, which make him a nice fit on any roster even if he is known to want to be more than a three-and-D player. Anunoby has a year left on his contract and will command more money next summer as a free agent than the Raptors can offer him by way of an extension.

We say Anunoby in part because the Trail Blazers have long had an interest in the burly forward and — given their future payroll situation — would likely be able to offer Anunoby the kind of long-term deal the Raptors might have a hard time fitting onto their books.

As well, it’s believed Scottie Barnes — heading into his third season — remains the apple of the Raptors' eye and the talent they hope will help lift them back to Eastern Conference relevancy, with or without Lillard. For what it’s worth, there have been no back-channel feelers from the Blazers regarding the possibility that All-Star forward Pascal Siakam — who might be a good fit in a deal because he has one year and $38 million on his contract — would be open to re-signing in Portland.

That also makes sense because it wouldn’t make sense for Toronto to trade for a 33-year-old future Hall of Famer and not have two-time all-NBA forward Siakam on hand as a No. 2 option.

A deal involving Anunoby, Gary Trent Jr. and Thad Young works financially, along with the picks. Maybe it gets expanded a little and the Raptors get another body back — Nassir Little has caught their eye in the past — or the Trail Blazers insist on rookie sharp-shooter Gradey Dick, who the Raptors selected 13^th overall in June.

The mechanics of a deal are there, or could be.

But should Toronto make the trade? I don’t think so, though I don’t get a vote. It’s hard to see the Raptors becoming a contender with Lillard on the roster. This is a 41-win team with suspect depth to begin with, not the loaded 59-win team that ran 11-deep that Leonard took over the top in 2018-19.

But to play along, from the Raptors' point of view, the top half of the East is pretty shaky. Milwaukee and Boston are good but not great teams. I think Cleveland is much improved, but again not a dynasty-in-the-making. After that, a Raptors team featuring Lillard could imagine itself as having a puncher’s chance at a conference finals, something no one would give them now.

It would be risky, even beyond leveraging your future for the present. Lillard has been explicit that his first, second and third choice is to land in Miami, and it’s worth noting of all the other markets that could be in the mix, Toronto was signalled out in a "for instance" example in prominent reports as the one where Lillard wouldn’t report.

And this isn’t some new thing. A couple of years ago, not long after the Raptors won their 2019 championship, some Raptors players reached out to Lillard about the possibility of joining forces in the post-Leonard era and were instantly rebuffed. “How about you come to Portland?” was the gist of the response from Lillard.

There is also the matter of Lillard being represented by Aaron Goodwin, one of the most powerful agents in the industry and who likely feels no urge to do Raptors president Masai Ujiri any favours after the fallout from Ujiri’s decision to trade another prominent Goodwin client — DeMar DeRozan — for Leonard in the summer of 2019.

They are said to be on better terms now, but it took a long time. In a situation like this, an agent can’t prevent a deal, but he can make life uncomfortable for all involved.

Did we mention Lillard will be owed $63 million in his age-36 season?

Ultimately, Lillard’s leverage is limited. “If he wants to get paid, he will have to show up,” said one league executive. And the precedent for those kinds of antics was set when Ben Simmons held out on the Philadelphia 76ers in advance of the 2021-22 season. The big guard was eventually dealt to Brooklyn, but being present though not available in Philadelphia for the first five months of the season cost him about $20 million out of pocket, per league sources.

Between the minimum games-played standard for player awards, the new language regarding the league’s player-resting policy and the way the Simmons situation worked out, the message is clear: the league office expects players under contract to perform.

As well, Lillard’s professional reputation is that of a low-maintenance star who wants to compete. Sitting out or slow-playing his way out of town — "the James Harden" — seems out of character.

So, there may be a deal to be done. It’s a deal that would likely improve the Raptors this season, but with little guarantee of a championship-level return, while requiring the bulk of their future draft capital to pull it off.

That’s where things stand as the Raptors enjoy their last week of the off-season. Things could look very different by next Monday in Portland, and maybe in Toronto, too.