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Damian Lillard Is Not A Raptor… Now What?

Frontrunners, they are no longer.

The long and enduring Damian Lillard trade fiasco has finally come to an end, with the all-NBA guard headed to not Miami, not Toronto, but Milwaukee to team up with Giannis Antetokounmpo. Safe to say, it’s a massive move for the Bucks who now have two All-NBA talents on their roster and have seemingly done enough to ease any concerns about the Greek Freak asking out in the next couple of seasons. It’s also a big trade for the landscape of the NBA, as the Blazers enter a rebuild centered around Scoot Henderson, Shaedon Sharpe, Anfernee Simons, and the recently acquired Deandre Ayton, and any team who attempted and failed to trade for Lillard is left trying to pick up the pieces.

But the Raptors were already in pieces before getting involved in the Lillard sweepstakes. If losing Fred VanVleet this summer wasn’t enough, they now have 3 core pieces, Pascal Siakam, O.G. Anunoby, and Gary Trent Jr. all heading into the final years of their respective contracts — all with pay raises on their mind. Ultimately, getting involved in the Lillard rumours was merely a way to paper over some of the mishaps, a get-out-of-jail-free card for a front office and a franchise that, by all indications, has refused to pull the plug on this core at every step of the way.

The recent indecisiveness from the Raptors has seemingly put them in an evolvingly precarious position — with little leverage to negotiate trades for their 3 upcoming free agents, and with Lillard and Giannis buddying it up in Cream City, no real, tangible way to improve this team.

And while there have been multiple rumours swirling about how far the Raptors went to acquire Lillard — they ultimately were hesitant to make a big swing. A league source close to the situation suggested to me that the Raptors indeed did not include Anunoby in their final offer for Lillard, and at best, offered something centered around Trent Jr, their 2023 draft pick Gradey Dick, Precious Achiuwa, and salary filler and picks to match — with Trent Jr presumably being re-routed to Phoenix, similar to the 3-team deal that went down today.

Portland instead decided to go the other route. Whether that’s because Lillard had an affinity for playing next to Giannis or just because the Blazers liked the Bucks package more is still yet to be determined. In all likelihood, it was probably a mix of both.

Nonetheless, the Lillard rumors are over and the Raptors are still headed toward another middling season with important contract negotiations on the horizon. History is repeating itself. And something has to pan out.

Trying to be optimistic: there’s a world where Scottie Barnes makes the leap to All-Star status this season, newly-signed guard Dennis Schroder gels perfectly with this nucleus and Dick, Otto Porter Jr, Anunoby, and Trent are enough floor-spacing to keep this teams offense afloat. Despite the spacing issues in the front court with Barnes, Siakam, and big-man Jakob Poeltl, rookie head coach Darko Rajakovic invokes a unique, motion style of offense that mitigates those concerns and their defense helps them win games on a nightly basis.

And now the negative: Barnes is being thrust into the point-guard role, and while he might enjoy playing that position, the data and film suggest that he still has a long, long way to go before being a viable starting point guard, if ever. Barnes is better suited as a playmaking hub with shooting and creation next to him and the Raptors are severely lacking in that department, even in spite of the addition of the rookie Dick and a presumably healthy season from Porter Jr. For how much of an offensive guru Coach Rajakovic could be, it doesn’t take a rocket scientist to know that this team will still struggle in the half-court, spacing wise, and that will make things even harder on their All-NBA talent Siakam to operate in the paint.

Ultimately, this Raptors team is one that’s bound to be stuck in the middle of the Eastern Conference, at least for the time being, until they potentially have 3 free agents walk on them this summer. Milwaukee and Boston both look like they’re ready to contend for a title this season. Miami, Philadelphia, Cleveland, and New York are bound to be playoff teams again. Indiana, Orlando, Atlanta, Chicago, and even Brooklyn added depth this summer and are hoping to make things interesting for the 4 play-in spots.

The Raptors standing in the East is very quickly dwindling, as is their potential future if they don’t find solutions… and quickly.

This team needs to choose a direction. With contracts expiring and the team just not being good enough to rationalize diving into the luxury tax — what can they feasibly do?

Let’s go through their options.

Trading Siakam

It’s a popular option and ultimately something they should have considered doing more seriously at last year’s trade deadline when Siakam still had 1.5 years left on his deal. This wouldn’t be the first time the Raptors have looked to see what deals are available for Siakam. At the 2021 draft, they were offered a package by the Warriors of picks and young players that they turned down reportedly. This summer, both Indiana and Atlanta have offered up deals for the two-time All-NBA forward, but ultimately, it hasn’t been enough for the Raptors to bite.

Perhaps they were waiting to see how the Lillard situation unfolded. Theoretically, it would’ve only made sense to pair Lillard with Siakam, and with that option gone now, maybe they revisit the deals offered by Atlanta and Indiana.

Doing so before the start of the season would clean up any questions about direction, it’d make the team more Barnes-focused and you would have one less contract negotiation lingering over your head. There’s a cleanness to this idea, although you’re probably losing your franchise player for pennies on the dollar with little to no leverage to negotiate for more.

Extending Siakam, Trading Anunoby, and Trent

I have it on pretty good authority that the Raptors have no intention of bottoming out any time soon. While trading Siakam is a clean option directionally, it would almost ensure that they’d be at the bottom of the Eastern Conference for the next few seasons until Barnes and crew develop into something real and tangible. With a potential sale of the team’s parent company, MLSE, on the horizon, there is pressure on the Raptors’ front office to keep this team treading water. In the end, playoff revenue, and gate revenue help with the company’s evaluation, and by retooling, you ultimately lose out on some extra dough. Not to mention the Raptors also have a top-6 protected 2024 1st round pick out the door to San Antonio — so bottoming out this season may not be in their best team-building interests either.

By extending Siakam, you allow yourself some extra breathing room. You give yourself at least a couple of more seasons to figure out where you’re at — and as long as Siakam continues his All-NBA level play, you can re-visit trading him, with leverage in hand because of the multi-year contract.

But that also means that you won’t be able to pay Anunoby or Trent… which most likely means trading one, if not both of your best shooters on the roster outside of the unproven Dick. Maybe those two can help you get more shooters? Maybe there’s an unknown deal out there that gives you prospects that can shoot and are relatively cost-effective? But, it’s a slippery slope.

Doing Nothing

Inevitably, doing nothing is also an option. A route that the Raptors have taken a few too many times in the past few seasons and it’s led them to this point. At this juncture, doing nothing and allowing for 3 key players to enter free agency, with the amount of talent that has left this franchise since their 2019 title run, would be malpractice.

But the Raptors have conventionally gone to the beat of their own drum, and there’s no telling how patient they’re willing to be when it comes to offers for their respective free agents.

Time started running out last season at the deadline, but now it’s about to expire. And it will no doubt bring about questions as it pertains to the future of the Raptors front office, helmed by Masai Ujiri and Bobby Webster.

The worst thing to be in the NBA is mediocre. And with the Raptors’ indecisiveness the last few seasons, and their near swing-and-misses on the likes of Donovan Mitchell, Kevin Durant and now Lillard, they’ve squarely landed themselves where every team dreads being…

The middle.