Here we go again.
Around this time last year, I wrote about the case for and against the Toronto Raptors signing Pascal Siakam to an extension before he became a restricted free agent.
This time, it's OG Anunoby's turn.
Three years removed from being drafted by the Raptors, Anunoby is eligible to sign a rookie scale extension before the start of the 2020-21 season. As was the case with Siakam, there are certain ways the Raptors benefit from signing Anunoby to an extension now, but there are also benefits to waiting it out.
What are those benefits? Let's take a closer look.
Why the Raptors should extend Anunoby now
There's a decent amount of risk involved in delaying Anunoby's extension.
If Anunoby doesn't sign an extension with the Raptors this offseason, he will become a restricted free agent next offseason, meaning he will be able to field offers from any team in the league. The Raptors would have the option of matching any offer sheet he signs, but allowing him to become a restricted free agent would open the door to Anunoby getting a deal that they aren't comfortable matching.
Where it gets tricky is that it's hard to put a number on what Anunoby's extension might look like. At least with Siakam, he seemed destined to sign a max extension, whether it was last offseason or this offseason. With Anunoby, there's still a lot up in the air.
MORE: Grading Anunoby's regular season | Grading Anunoby's postseason
At the very least, Anunoby has proven to be a reliable 3-point shooter and one of the most versatile defenders in the league. That combination makes him an incredibly valuable role player, the type any team in the league would love to have at the right price. However, Anunoby showed this season that he still has a lot of untapped potential. Expecting him to make a Siakam-type leap next season might be unreasonable, but he's shown that he still has a lot of developing to do.
One figure that has been thrown out there by ESPN's Bobby Marks: $70 million over four years. That might be overpaying Anunoby based on the player he is right now, but it could very well become an underpay depending on how much he improves.
Take Stephen Curry as an example. Back in 2012, the Golden State Warriors signed him to a four-year, $44 million extension. While some considered it to be a risky deal at the time - it's easy to forget that Curry dealt with ankle injuries early in his career, raising questions about his durability - it turned out to be one of the best bargain deals in NBA history, as Curry was still on his rookie scale extension when he won both MVP awards.
Now, it's safe to assume that Anunoby will never reach the heights Curry has, but there is a world in which the Raptors sign Anunoby to an extension this offseason that might look like an overpay but turns into a bargain because of a leap he eventually makes, similar to what happened with Curry.
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Additionally, there's a goodwill element to getting a deal done early. Anunoby has proven to be a big part of Toronto's present and future, so committing to him now sends a clear message that they value him as a key piece of the franchise moving forward. As I wrote last year, we've seen how teams letting restricted free agency set the market for a player can come back to bite them, maybe not immediately, but down the road.
For what it's worth, the Raptors have a history of extending players early, from Siakam to Kyle Lowry and Norman Powell. It'll be interesting to see if that trend continues with Anunoby.
Why the Raptors should wait to extend Anunoby
There are three reasons that come to mind.
The first? The Raptors will still have the option of matching any offer Anunoby receives next offseason, so not extending him this offseason doesn't mean he's gone.
The second? The Raptors would get to see how Anunoby develops over the next year, which could provide some clarity over what his extension should be.
The third? The Raptors would maximize their cap space for 2021 free agency.
The third reason is the big one. Right now, Anunoby has an $11.6 million cap hold for the 2021-22 season. If he were to sign an extension this offseason, his salary in the first year of his extension would replace that number.
In other words, anything over $11.6 million in the first year of his extension would eat into the max amount of cap space the Raptors are currently projected to have.
MORE: What's next for the Raptors?
The reason that matters: 2021 is the summer in which a number of Tier 1 players could become free agents, including Giannis Antetokounmpo, who the Raptors are reportedly hoping to pursue should he become available. According to Basketball Insiders, the Raptors currently have $31.1 million committed to their roster for the 2021-22 season, giving them plenty of room to offer a max contract to someone like Antetokounmpo, but that doesn't include Anunoby's cap hold, Powell's $11.6 million player option and whatever Fred VanVleet makes on his next contract should he re-sign with Toronto this offseason.
As Blake Murphy of The Athletic recently detailed, it's not impossible for the Raptors to keep VanVleet and have max cap space in 2021, but Powell picking up his player option and Anunoby signing an extension this offseason would make it incredibly complicated.
We don't have to go down every scenario right now. (Again, Murphy did a nice job of breaking it down if you're interested). Just know that strictly from a keeping-the-books-as-open-as-possible-in-case-Antetokounmpo-decides-to-jump-ship perspective, it makes the most sense for the Raptors to delay Anunoby's extension until next offseason.
The only caveat is if the Raptors can come to terms on an extension that pays Anunoby less in 2021-22 than his $11.6 million cap hold, but that seems highly unlikely to me.
What's at stake for Anunoby
I'll keep this simple.
Signing an extension now locks Anunoby into life-changing money and takes the risk out of a slip in play or an injury impacting his future earnings.
Signing an extension next offseason gives him another opportunity to increase his value and use it as leverage in restricted free agency.
It gives Anunoby and the Raptors a lot to think about between now and the start of next season.
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