A Damian Lillard deal is nothing to be afraid of.

It’s been... muddy in Toronto these past few years. After the high of the 2019 title, and then a valiant run through the bubble in 2020, life for the Raptors has become unsettled. With team President Masai Ujiri, and General Manager Bobby Webster seemingly trying to have their cake and eat it too by trying to build a win now AND win later team.

It’s a stance that has frustrated large swaths of the fan base, and even the media covering the team. The calls have grown louder and louder for Ujiri and Co. to pick a lane - preferably the marked one ‘rebuild’. Every misstep, including Toronto underestimating the lengths to which Houston would go to sign two time All-Star point guard Fred VanVleet, is met with hostility and questions on whether Ujiri has lost his fastball.

Well, clarity, she seems to be a-coming.

On Monday, ESPN’s Marc Spears reported that the Toronto Raptors were the “frontrunners” for the services of the seven-time All-Star (a report that was presaged last week by Dame’s camp just happening to choose Toronto as the ‘for instance’ team that Dame wouldn’t report to).

I may have jumped the gun on how quickly the Raptors would get serious about Dame, but the argument for why Dame could kill it in the 6 remains the same. A pick-and-roll pairing between Pascal Siakam, one of the five most efficient post scorers in the league last year, and Dame, arguably the best volume shooter in the NBA not named Steph Curry, has the potential to be a championship level backbone play.

Dame would bring with him the defensive issues that Portland could never fully figure out, but even after a potential deal, Toronto would have a bevy of long wings, and mobile rim-protecting centres to insulate Lillard.

If the fan base’s issue is staying in the dreaded middle, then a Lillard deal solves that. The future is clear. Contend.

The thing is, as long as the price isn’t ridiculous, the Raptors, and by extension the fans, can’t lose a Lillard trade. Just pulling it off, even if it doesn’t work, goes a long way to re-establishing the idea that Toronto’s front office are swashbucklers, capable and bold enough to pull off the most audacious of moves. That sort of moxie is what stars want in finding a new team, especially one that is, to be charitable, more of a B-tier destination when compared to Los Angeles, Miami, Golden State and maybe finally again, New York.

The permutations of a Dame deal have been discussed ad nauseum, so I won’t beat a dead horse, but as I mooted back in that July piece, a deal of Lillard for OG Anunoby, Chris Boucher, Thad Young and Malachi Flynn works money wise. Toronto would need to add picks to the deal, but Anunoby is so much more valuable to Portland than Tyler Herro is, there is a world where two picks, perhaps unprotected ones in 2027 and 2028 - the final year of the Lillard deal, and the first one after, when Toronto could be going through a transformative period, would be enough to get the job done.

(Spare me with the: “But, Portland could flip Herro to get what they really want!” line. If a market existed that would turn Herro into mulitple firsts or a young two-way wing, that deal would be done by now, and those assets would be winging their way to the Pacific Northwest.)

The point being is that the Raps can bear losing one future young asset, and a pair of lightly or unprotected picks and still be in a good position even if the Lillard experiment fails. It seems almost impossible that Lillard would actually refuse to report to Toronto - given the money he could lose, and his reputation as one of the league’s true grinders.

Realistically, the worst case is Dame and the Raps give it a run, it doesn’t work out, and by the deadline Toronto ends up trading Dame to a team like Miami in a deal that gets them 60-75-cents on the dollar compared to what they paid for him in the first place.

At that point the the Raps are firmly in rebuild mode with Siakam, Trent Jr., and maybe even Poetl sent out the door. Again, clarity. Albeit with a few less assets than they could have had in a rebuild, but for a shot at some meaningfull basketball while an All-NBA talent like Pascal Siakam is still in his prime, that seems a reasonable cost.

Yet, for a franchise that took a similar big swing that ended up in a title just five years ago, the reaction to trading for Dame has been surprisingly muted. The narrative is all: ‘Dame is too short’. Or, ‘Dame costs too much.’ Or, most tellingly, ‘even with Dame there is no guarantee the Raps can get to the Conference Final, let alone the NBA Finals.”

Yes, Lillard is 33. Yes, he is signed to an ungodly amount of money through his 36th birthday. Yes, Lillard has never lead a team past the Conference Finals. This is not Kawhi Leonard, a player who was in the conversation for best in the league.

Still, Lillard is good. He is an offense unto himself, a sure fire Hall of Famer, and arguably the greatest mid-major success story in NBA history. While he may not be someone who is a threat to win MVP, he has five top-10 finishes on his resume, and its fair to argue that if last year’s Trail Blazers had been a better team, Lillard’s age 33 season, where he put up a career high 32.2 PPG on career best efficiency would have made it six.

It’s also said that this is not the 59-win Raptors making the move for Leonard. That the best this 41-win Toronto team could be with Dame is a team that bravely goes out on its shield in the second round.

It’s true, a Dame deal does not make Toronto the unquestioned number one contender to knock off the Nuggets, but it’s worth noting that Boston, the team that has been considered the most talented in the East, if not the whole NBA, for three years running, has made the Finals just once in that span - and just traded their heart and soul when many observers said those were exactly the qualities they were missing.

Run down the list and you’ll see issues with every major Eastern contender - Miami shed a ton of their depth and before their insane playoff shooting performance were barely better than the Raptors. Milwaukee is a year older, still has half-court offense issues, and has a star openly musing about the future. Philly has the James Harden affair to manage, and also has seen their franchise player wonder what could be next - not to mention Joel Embiid might be hurt more than anyone else by the new rest rules. New York is good, but is looking for exactly the type of star talent that Lillard represents. The Cavs have potential but it’s tied into Evan Mobley taking an offensive leap he may not have in him. Teams like Indiana and Orlando are getting interesting, but if you’re afraid to take a big swing because the Pacers might gel - you’re in the wrong business.

Nothing is guaranteed, and if you are going to take a swing, why not do it in a period of relative unrest?

If a Lillard deal requires more than Anunoby or Barnes and a couple of firsts - say the Blazers refuse to do a deal without Grady Dick, or two more firsts, than by all means Toronto should walk away, and let Portland take their chances on Tyler Herro, his uneven fit and his $120 million deal.

At worst, if a Lillard deal doesn’t work the Raps will take a loss on the exchange between acquiring Dame and moving on from him, but will gain clarity on future direction.

At best, a Dame-led team could be catnip for someone like Giannis to join (for those who think that the Raps should keep their assets so they can go get Giannis in a year or two, why on earth would Antetokounmpo, who’s biggest complaint is whether Milwaukee has the supporting cast to help him win now, want to come to a Toronto team that has traded all their impending free-agents for players or picks that will need years to give him that support?)

Most likely, a Dame deal would lead to some exciting years, but fall short of a title. Still, Raptors fans shouldn’t be so quick to dismiss the meaningful chance at a three-to-four-year run of high-stakes basketball led by a future Hall-of-Famer and an All-NBA talent that also gives players like Scottie Barnes and Dick meaningful reps in high pressure situations. If the idea that playing meaningful basketball develops players fastest is true, Barnes may end up in a better place than if he were handed the ball to do whatever the hell he wants on a 30-win team.

In the NBA, the winning teams are the ones who reach for the highest ceilings, it may not match up quite as neatly as 2019 did, but a Dame deal that comes in at a reasonable price is Toronto’s clearest path to get to that ceiling.

(And hey, I don’t mind taking my chances on a Ujiri-Webster front office that’s all in on a rebuild, I’d just rather it come on the path that took a swing at greatness first.)