Raptors Sit at Crossroads With Questions Mounting After Missing on Damian Lillard Deal

The Toronto Raptors continue to sit in no man's land unable to contend and unable to tank following Damian Lillard trade saga

And now it’s back to the drawing board for the Toronto Raptors.

Regardless of how much Damian Lillard would have actually moved Toronto’s championship odds this year, a deal with the Portland Trail Blazers for the 33-year-old superstar would have sent the Raptors down a clear path forward. It would have sent a message: We intend to win. But instead, Lillard is heading to the Milwaukee Bucks and Toronto is once again stuck in the middle.

Now there are questions abound for the Raptors with the season set to begin in less than a month. What, for example, is the plan for this organization going forward?

The Raptors were a 41-41 team last season and watched a former All-Star Fred VanVleet walk out the door in free agency without anything in return. Sure, free agent acquisition Dennis Schröder will be able to replace some of VanVleet’s value, especially on the defensive end, but for a team that struggled so mightily with floor spacing and shooting last season, VanVleet’s departure is certainly a net negative for the organization.

That should have been a learning lesson for Toronto that anything can happen in free agency. Nobody would have expected VanVleet to ink a max contract during last season, but when the Houston Rockets spurned James Harden for better leadership, the Raptors were suddenly caught with their pants down.

And yet, with just days to go before training camp starts, the Raptors find themselves in a familiar spot. Pascal Siakam is heading toward free agency next summer, without a contract extension being discussed, per Sportsnet’s Michael Grange. O.G. Anunoby is essentially in the final year of his contract and is unlikely to sign an extension with the team as Toronto’s max extension offer to him is capped at a number less than what he’s worth. Then there’s Gary Trent Jr., who’d been rumored to be nearing a contract extension with the team months ago, but for now remains unsigned past this season.

That’s a former All-NBA player, an All-Defense player, and a combined 46 shot attempts per game from last season heading toward free agency next summer. For a team that dealt with “selfishness” issues last season, as Raptors president Masai Ujiri put it, that should be a concern.

Extensions for the trio would solve part of the problem, but that would put Toronto either up against or into the luxury tax for a team that has so far shown no postseason success. If history is any indication, a luxury tax bill for a non-championship caliber team is not something ownership would find appealing.

That said, there’s no obvious way out of this issue either. One option would be to rip the Band-Aid off, quit preaching patience, and make the kind of trade Toronto, in hindsight, should have made with VanVleet. The further Siakam, Anunoby, and Trent are from free agency, the more value the three should have to acquiring teams. Selling one, two, or all three of Toronto’s free agency trio would allow the Raptors to quickly pivot toward a rebuild around former Rookie of the Year Scottie Barnes.

There is, however, an issue with this plan: Toronto’s missing 2024 first-round pick. The stick-to-itiveness of the last trade deadline has limited the Raptors’ options for this year. Sure, they could pivot toward a rebuild, take a step back this season, and sell those aforementioned free agents, but that almost certainly means gifting the San Antonio Spurs a lottery pick courtesy of the Jakob Poeltl deal.

There’s a quote that’s been attributed to Teddy Roosevelt that feels applicable in this moment for the Raptors: “In any moment of decision, the best thing you can do is the right thing, the next best thing is the wrong thing, and the worst thing you can do is nothing.” No, doing the wrong thing isn’t ideal, but at least it would move Toronto down a path in one direction or another. The longer they do nothing, the worse things seem to get.