Dame Time Machine: Are the Raptors about to shock the NBA again?

These are the type of moments Masai Ujiri lives for. The chance to make bold, but calculated, plays. To swing for the fences knowing that if it doesn’t work you’re still in position to smash a double off the wall.

This is also one of the reasons Ujiri teams generally eschew the tank - when stars who could completely change the trajectory of your franchise come available, Masai, Bobby Wesbter and Co. like to have the infrastructure and the right-now talent to make a play for them.

Enter Damian Lillard.

Yes, Dame has said he wants to play in Miami. Yes, stars seem to always get their way in the modern NBA.

But then you hear what Blazers G.M., Joe Cronin said: “We have been clear that we want Dame here but he notified us today he wants out and he’d prefer to play someplace else. What has not changed for us is that we’re committed to winning, and we are going to do what’s best for the team in pursuit of that goal.”

Or in other words, we love and respect Dame, but if Miami isn’t making the best offer, we aren’t trading him there.

The fact is Miami’s best offers all centre around some combo of Tyler Herro, Kyle Lowry’s expiring contract, or Duncan Robinson’s deal, two recent first round picks who have a combined 200 NBA minutes between them (Nikola Jovic and Jaime Jaquez), and, a pair of firsts they can’t trade until almost the end of the decade.

It’s a deal that has merits, but for Portland it is complicated by the fact that Herro is a worse version of Dame - a great scorer, but a defensive liability. It’s also a player-type they already have in Anferne Simmons and Shaedon Sharpe (though Sharpe may end up a much better defender). A trade for Herro is a move that demands other moves.

Enter Toronto.

The Raps have the type of players the Blazers largely don’t - versatile wings who can defend multiple positions and insulate a still-small Blazers’ back-court. The Raps have largely unfettered control of their picks (the top-6 protected first owed to the Spurs in 2024 is a complication, but only a tiny one - if the Raps want to make a Lillard deal, they could easily remove the protections on the pick).

There are a few ways to go about trying to acquire Lillard. One, is a deal that centres on Raptor’s star Pascal Siakam, but if you’re Masai and Bobby Webster, you don’t want to do that because Dame and Siakam are EXACTLY the two player types you want to combine.

Siakam quietly just put the finishing touches on his best year ever. A season that saw him put up 1.10 points per post-up possession - a mark that was 5th in the league and virtually tied with Joel Embiid (stats courtesy of Second Spectrum).

A pick and roll combo with Dame and Spicy P would be a problem. Dame is of course a threat to fire with an inch of separation, Siakam is a good enough screener to get him that inch. While Siakam wouldn’t be an insane pick and pop threat, his improving mid-range game means he could generate enough good looks from beyond the arc or in the mid-range to force opponents to honour it. And, as we just referenced, teams switching that pick and roll are inviting Siakam to mash them. Even teams that might have a 6’6 athletic freak chasing Lillard around are going to need to send help on a switch. If Siakam, three inches taller, gets that guy down low? It’s an emergency. If he’s 6’3? It’s a five-alarm fire. Jam Siakam as he tries to roll? Then Dame is taking the big, and gliding to the tin, forcing rotations. Stay at home on both? It’s still mis-match city. Or, maybe Lillard gives up the ball, relocates to the weak side, and Siakam gets to attack one-on-one with space.

Siakam is of course a canny passer, more than capable enough of picking apart the double-teams that would come when he rolls. Dame is a great passer too. Trap Dame, and Siakam can play the Draymond Green role, but with waaay more ability to score.

In short, it would be a nightmare scenario.

The move also makes sense for Lillard. With Siakam, Barnes and even players like Gary Trent Jr. empowered and able to bring the ball up the floor, Lillard would be able to do his best Steph Curry impression, moving without the ball in terrifying and defense-contorting ways. Off-ball Dame forces teams to both watch the man with the ball, and Lillard with equal levels of urgency. Lillard would save himself the pounding and stress of having to create each and every action, as he usually did in Portland, but would still be the unquestioned late game initiator.

The Raps also have the size to insulate him in a way Portland never could (and Miami currently can’t). Jakob Poeltl may not be the absolute best version of a modern switchable NBA big, but he’s pretty damn good, is an elite rim-protector, and would be a fantastic pick and roll partner himself.

Siakam, Barnes, OG Anunoby, Chris Boucher, Precious Achiuwa, the newly acquired Jalen McDaniels and even Thad Young provide size and savvy to back Dame up when he is targeted by the opposition, and overall, Toronto has enough defensive talent to consistently stash Lillard on the opponent’s weakest offensive player, freeing Lillard up to do what he does best on defense - anticipating the play and jumping into it to cause steals and fuel what would still be a lethal Toronto transition game.

Of course, not all these pieces would be here after a Lillard trade. Portland is going to want some of those so their Simons, Sharpe back-court can start to cook ASAP, and this is why Ujiri has resisted Toronto tearing it down. He has pieces that are good now, not maybe in three years, and where project 6’9 pays dividends - the Raptors best players can fit on almost any team.

Toronto could offer Portland a deal in this vein: Anunoby, Boucher, and the expiring deals of Young, Malachi Flynn and Joe Wieskamp, plus three first round picks and pick swaps as required to get the deal done.

Doing so leaves the Raps looking something like this:

PG: Lillard, Schroeder, Barnes

SG: Trent Jr., Dick, Schroeder

SF: Barnes, McDaniels, Porter, Dick

PF: Siakam, Achiuwa, McDaniels

C: Poetl, Koloko

You definitely miss Anunoby’s lockdown defense, but Precious Achiuwa has shown flashes of O.G.-like versatility and verve. McDaniels helps there as well, as of course, does Siakam.

The Raps would still be a little light on shooting, as it would be tough to get more than three of Dick, Porter, Lillard and Trent Jr. on the floor at the same time, but Poetl provides vertical spacing, and maybe McDaniels shooting 38-percent from three in Charlotte a year ago, and 40% in limited time with Philly last year, is real. Or, real enough.

Hell, maybe Achiuwa settles in the 35% range for a full season. It’s not blistering, but with all the open looks Dame and Pascal, or Dame and Poetl, or Dame and Barnes (we haven’t even talked about how much easier Dame could make the game for the still learning former rookie-of-the-year), that sort of proficiency would be enough to punish teams for abandoning Achiuwa at the arc. Precious has also shown enough off-the-bounce juice to cause problems on sloppy close-outs. Not to mention the offensive rebounding opportunities that would come if he’s given free reign to attack the glass.

For Toronto, the fit is perfect. It instantly vaults the Raptors into the upper echelon of contenders, slots Siakam in the proper spot in the offensive pecking order, and allows a massive Toronto team to cause problems for anyone else in the NBA - afterall, the Nuggets taught us that size still does matter.

If I’m Portland, the fact the trade is a lot more plug and play than the Heat’s deal is enticing. Anunoby is a highly-coveted piece and would fit perfectly beside Josef Nurkic and Jerami Grant in the Blazers front court - he and Grant would go a long way in masking the dynamic Simons own Dame-esque defensive issues. Boucher is a versatile, valuable third big, or a change of pace player who gives them size and the ability to go small and fast and still protect the rim if the Blazers sit, or deal, Nurkic. If Boucher is closer to the 38% three-point shooter he was in ‘20-21, and the second half of last year, the Blazers are making out even better. Young is more a contract, but he’s still a savvy passer and defender who might have a role in Portland, or could be rehabilitated enough to send out for another asset at the trade deadline. I feel bad for Flynn as he lands in another NBA city that doesn’t really need what he brings, but maybe he can carve out a 4th guard role. Wieskamp is the threat of a shooter, but is really just here to make up the numbers.

Plus, you have an extra first rounder in this deal. Portland could ask for one pick in the near-term to bolster their burgeoning core, and then angle for the next two to be after Lillard and Siakam have passed their prime, maximizing the Blazer’s ability to get top picks.

Of course this is not a fait accompli. The Brooklyn Nets, another favoured Lillard destination, have the capital and players to compete with a Raptors offer. Lillard may prefer to stay in the United States and therefore the Blazers may rule out Toronto entirely (why antagonize the face of a franchise by sending him to the one city he doesn’t want to go to ?). Portland may not value Anunoby the same way they did six month ago, given Dame will be gone, or they may want multiple young players - asking for Gradey Dick, say, and push the Raps out of their comfort zone...

Still, there is the outline of a workable deal here, and Ujiri and Webster have proven they have an ability to be bold and flexible. The Kawai Leonard situation is still fresh in everyone’s mind as an example of why this could work. While Toronto may not be one of his stated destinations, Lillard would be blind not to see the potential parallels. He’s also patiently spent years in Portland being the consummate professional. Maybe he would throw a fit if he didn’t get to where he wanted to go, but there is a lot of evidence that Lillard would swallow that disappointment - especially if he sees a route to the ring he’s wanted his whole career.

Think about it, the NBA is as wide-open as it has ever been. Combining Lillard with an All-NBA talent like Siakam, a top young player like Scottie Barnes, and versatile veteran pieces like Poetl, Trent Jr., and Porter Jr. absolutely puts Toronto in the mix.

If you’re Lillard, potentially repeating the Leonard arc in that wide-open NBA, and becoming a hero in a second NBA city, a city that, like Portland, absolutely venerates it’s players, while also having the chance to soak up business deals in what is, in effect, a 40-million person market, could be, no, screw that, should be tempting.

The stage is set for Toronto to again shock the NBA world by scooping up a fallen star. No, Lillard isn’t a do-it-all total alpha in the way Leonard was, but he doesn’t come with the flight risk, or (admittedly overblown, at least in Toronto) character and injury questions of Leonard either.

Going all-in for Lillard would be a bold move, but it would be very on brand for Ujiri, and, thanks to the way he believes in team-building, a very possible one as well.