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TSN Raptors Reporter

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TORONTO – The NBA pre-season rarely serves as anything more than an appetizer, a small taste of what’s to come, with the main course – the start of the regular campaign – just around the corner. Occasionally, it gives us something that’s worth taking note of, though.

Early in the Raptors’ exhibition opener against Charlotte on Saturday – a game in which Toronto overcame a 19-point first-quarter deficit to win 111-100 – OG Anunoby had one of those standout moments.

Looking to run after creating a turnover in the backcourt – a staple of Nick Nurse’s system – Fred VanVleet pitched the ball ahead to Anunoby, who led a one-on-one fast break. When Hornets prodigy LaMelo Ball – the only defender in front of him – reached to go for the steal, the Raptors’ forward shook him with a behind-the-back dribble and went in for the uncontested two-handed slam dunk.

Even in a game that didn’t count, those are the types of plays that catch your eye, and you can bet Toronto’s brass was paying close attention, as well.

The Raptors have until Monday to sign Anunoby to a rookie scale contract extension. Like many folks around the league, the team believes the 23-year-old forward is in line for a breakout fourth NBA season, and there’s little doubt that they see him as a big part of the future.

They have every intention of locking him up long-term, but there is some question as to how and when they do it.

Tuesday’s landscape-shifting news, that Giannis Antetokounmpo plans to sign his super-max extension and remain in Milwaukee, could also impact how the Raptors’ decision on Anunoby plays out.

There are several valid reasons to extend Anunoby ahead of the December 21 deadline – cost certainty, and buying goodwill with the player and his representation, are chief among them – but in spite of them all, it seemed unlikely that anything would get done, until Antetokounmpo made his commitment to the Bucks.

The primary benefit to waiting until the off-season, allowing Anunoby to become a restricted free agent, and signing him – or matching an offer sheet – then is to maximize cap space for next summer, which has been a top priority for Toronto. As a free agent, Anunoby would remain on the books for his cap hold of $11.6 million, as opposed to the first-year salary of his new deal if they were to extend him, which would probably be in the neighbourhood of $15-to-20 million.

With only Pascal Siakam, VanVleet and Malachi Flynn under guaranteed contract past this season, the Raptors have given themselves the flexibility to open up enough room to sign a max player on the open market. In this scenario, they could theoretically use their space on a big-name free agent, then exceed the cap – and likely go into the luxury tax – to retain Anunoby using his Bird Rights.

Given the recent emphasis on keeping their books as clean as possible following 2020-21 – it’s the reason why Kyle Lowry was only given a one-year extension last fall, it’s why VanVleet’s new deal was negotiated with a dip in salary for his second season, and it’s why they weren’t more aggressive in pursuing Serge Ibaka or Marc Gasol in free agency – that appeared to be the Raptors’ plan.

"I think there are talks to be had," team president Masai Ujiri said earlier this month, when he was asked about the possibility of extending Anunoby. "They know of the abilities that we [have], so we’ll keep having those conversations."

The implication there was that unless Anunoby and his reps are willing to take a significant discount to get a deal done now – likely something close to that cap hold of $11.6 million, which is far lower than what they’re asking for – it will have to wait until the summer.

However, things have changed. With Antetokounmpo – Toronto’s presumed top target in free agency – off the board, would Ujiri and general manager Bobby Webster be more inclined to eat into their coveted cap space in order to secure Anunoby’s future with the team? The answer, most likely, is that it will depend on the cost.

Anunoby’s camp is believed to be seeking something in the ballpark of the four-year, $85 million deal that VanVleet got last month. The team will likely come back with an annual figure closer to $15 million. Would both parties be agreeable to a compromise in the range of $17-to-18 million annually?

At that price, the path to opening up a max slot next summer would become far more complicated, verging on impossible, and would probably take the Raptors out of the running for top tiered free agents like Victor Oladipo or Rudy Gobert. On the other hand, those guys don’t move the needle in the same way Antetokounmpo would have. Toronto would have its young core of Siakam, VanVleet and Anunoby under contract for the foreseeable future, and would still have enough cap space to chase a lower tiered free agent or two, and perhaps bring Lowry back.

Rookie scale extensions are tricky, though. These are players in their early-20s, they’re generally just starting to scratch the surface, and are a few years away from even sniffing their prime. Unless the player is a no-doubt superstar, you’re almost always projecting their value instead of paying them what they’re currently worth. Projecting value is especially difficult with somebody like Anunoby, who was a low-usage player in each of his first three NBA seasons.

Still, there’s a reason the Raptors are excited about Anunoby and expecting big things from him this year, and beyond. He’s already blossoming into one of the league’s best and most versatile defenders. Then, when you see moves like the behind-the-back dribble he executed in the exhibition opener – building off of the progress he made as an offensive weapon during his impressive third season – you can understand why people are high on his two-way potential.

Roughly a third of the league’s teams should have money to spend in next summer’s free agency sweepstakes, and the highly anticipated crop of players that could be available has taken a hit this past week, with Antetokounmpo and Paul George agreeing to extensions with their respective clubs.

In what could end up being a seller’s market, a rising star like Anunoby would almost certainly be in high demand, regardless of whether he takes the step many are expecting him to take this season. At worst, he projects as a starting "three-and-D" wing – a player-type that’s highly valued in today’s game. If he does in fact break out this year, he might be looking at max offer sheets in August, or whenever free agency opens following the expedited 2020-21 campaign.

Although the Raptors could match any offer he receives, the argument in favour of extending him now is that you can probably get him at a price closer to what he’s worth at his worst-case scenario than what he would be worth at his best-case scenario. Historically, Ujiri’s front office has looked to do that – signing Terrence Ross, Jonas Valanciunas and, most recently, Siakam to rookie scale extensions ahead of their fourth seasons with the team. The only notable exception was Delon Wright, who the Raptors opted not to extend and wound up trading – in the deal that landed them Marc Gasol – in the middle of his fourth campaign.

Anunoby’s case is unique, though. If the Raptors choose not to extend him by Monday, it won’t be an indictment of the player or reflect how they value him or view his importance to their future. However, the chances of them coming to terms on a new deal ahead of opening night are higher – perhaps a lot higher – now than they were a few days ago.