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TSN Raptors Reporter

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TORONTO – OG Anunoby and the Toronto Raptors have always seemed like a match made in basketball heaven.

For starters, we know Masai Ujiri, Bobby Webster and the team’s highly regarded front office staff love athletic and versatile, two-way wing players – they were pleasantly surprised when the talented Indiana product fell to them at pick No. 23 in the 2017 draft, a result of the knee injury he sustained in his last season at college.

Anunoby is famously a man of few words. Toronto is an organization that likes to keep its cards close to the chest. There isn’t a lot that needs to be said, anyway. For as coy as the Raptors can be about certain things, their feelings for Anunoby have never been a secret.

They refused to include him in the Kawhi Leonard trade with San Antonio after his promising rookie year. They stood by and supported the young forward throughout a disappointing sophomore campaign that challenged him both personally and professionally.

Now, following an impressive third season and with many – including the team itself – expecting him to take another big step in 2020-21, they’ve put their feelings into writing.

On the eve of opening night around the NBA, and just ahead of Monday’s deadline, the Raptors and Anunoby agreed to a four-year contract extension worth a reported $72 million. The deal reportedly includes a player option on the final season.

“OG is the epitome of the skilled, powerful, determined player we want in our organization long-term. Remember, he doesn’t shoot to miss,” said Webster, with a callback to Anunoby’s quip after knocking down the game-winning buzzer-beater against Boston in the playoffs last fall. “We’re really pleased that OG will be with us for seasons to come.”

In spite of their mutually beneficial relationship, there was some doubt as to whether they would come to terms on an extension, though it had nothing to do with how the team valued the player or envisioned his importance to its future. Both parties had good reason to be reluctant.

The Raptors have prioritized keeping their books as clean as possible following this season. Extending Anunoby now, as opposed to waiting and signing him as a restricted free agent – or matching an offer sheet – during the off-season would cut into their available cap space for next summer.

When Giannis Antetokounmpo committed to Milwaukee last week – thus taking Toronto’s presumed top free agent target off the board – it likely made an Anunoby extension more feasible on their end. The irony is it may have also made Anunoby and his camp think twice about locking themselves in.

The highly anticipated free agent class of 2021 has taken a substantial hit this past week, with Antetokounmpo, Paul George and, most recently, Rudy Gobert all agreeing to extensions. At the same time, several teams are still projected to have significant cap space to spend on what’s looking like a depleted crop of players, meaning there could have been some rich offers out there for somebody like Anunoby.

Would the Raptors opt to maximize their cap room – as they have to this point – and aim to re-sign Anunoby in the summer, when it would almost certainly cost them more, or would they sacrifice some of that space in favour of cost certainty with one of their young cornerstones?

Would Anunoby take the guaranteed money and long-term security now or roll the dice in the hopes of getting a bigger payday in eight months?

It was always going to come down to whether they could find a number that made sense for both sides. At $72 million over four years – or $18 million annually – they should each feel good about this deal.

For Anunoby, who tore his ACL early in his junior year of college and knows what it’s like to recover from a serious injury, the extension should provide some safety and peace of mind. It’s also a nice and well-deserved raise for a player that’s earned $5.9 million over his first three NBA seasons.

Meanwhile, this is great value for the Raptors. $18 million per year is not insignificant money, to be sure. Rookie scale contract extensions are almost always tricky – unless the guy in question is a no-doubt max salary player, which Anunoby isn’t, you’re going to be paying for projected value. Projecting value is especially difficult for a player like Anunoby, who has been in a low-usage role for the bulk of his career, to this point.

However, the market dictates value, as always. At worst, Anunoby projects as a very good, versatile ‘three-and-D’ starter at the wing positions. That’s basically what he’s already blossomed into, and it’s a player archetype that is highly coveted and paid well in today’s game.

To compare, the Pistons recently landed Jerami Grant – who’s two years older than Anunoby – in a sign-and-trade from Denver for $60 million over three seasons. Moments before Anunoby agreed to his new deal, the Clippers extended sharpshooter Luke Kennard for four years at $64 million – and he gives you the ‘three’ without the ‘D’.

Eighteen million dollars annually is already fair value for a player with Anunoby’s two-way skill set, and that’s not factoring in his immense upside. The 23-year-old is establishing himself as one of the league’s best perimeter defenders. He’s also showing flashes of an expanded offensive repertoire – the ability to put the ball on the floor, attack the defence, get to the rim, and make plays for himself and for his teammates. If he does in fact break out in a bigger role this season, there’s a reasonable chance he may have gotten max offers in what is shaping up to be a seller’s market next summer.

From a business standpoint, the extension secures a prized asset at a reasonable cost. On a personal level, it reinforces the idea that the Raptors take care of their own and reminds Anunoby and his representatives how highly they value him.

Over the past 14 months, the Raptors have signed their promising young trio of Pascal Siakam, Fred VanVleet and Anunoby to new deals. Factoring in opt outs, all three players are under contract for at least three more years and will be the foundation of whatever comes next for the franchise, and they still have plenty of flexibility.

The Anunoby extension will eat into their cap room for next summer, which likely means they won’t be in the mix for a max player in free agency, though there may not be many guys that are worth that kind of money out there, anyway. They should still be able to spend just short of the max, meaning they can add an impact player or two on the open market, or look to upgrade via trade.