Every offseason, teams have the chance to sign their former first-round picks – specifically, those who have just completed their third NBA season – to something called a rookie-scale extension, which must be agreed upon by Oct. 21.

Last summer, teams used this CBA mechanism to extend five players – Karl-Anthony Towns, Devin Booker, Myles Turner, Justise Winslow and Larry Nance Jr. – to deals ranging from the max (five years, $190 million for Towns) to regular, run-of-the-mill extensions (three years, $39 million for Winslow). And thus far this offseason, just three eligible players have been extended: Ben Simmons (five years, $170 million), Jamal Murray (five years, $170 million) and Caris LeVert (three years, $52.5 million).

There are others, however, still waiting for an extension.

One of those players is Toronto Raptors swingman Pascal Siakam.

Siakam, a 25-year-old small forward out of New Mexico State, is coming off the best statistical season of his career, one in which he averaged 16.9 points, 6.9 rebounds and 3.1 assists per contest on healthy 54.9/36.9/78.5 shooting splits. What’s more, he continued his outstanding play in the postseason, where he averaged 19.0 points, 7.1 rebounds and 2.8 assists, helping Toronto win their first NBA title and earning Most Improved Player honors for his efforts.

The advanced metrics also shine Siakam in quite a favorable light.

Box Plus/Minus (+3.4), Win Shares (9.3) and Value Over Replacement Player (+3.5) all placed Siakam’s 2018-19 campaign among the league’s 30 best, with the highest ranking coming in Win Shares, where the 6-foot-9 player finished 15th overall.

All in all, it would appear that – according to the production and impact to winning, at least – Siakam is more than deserving of an extension this summer, and probably a huge one at that.

What do executives around the Association think about that?

One former Eastern Conference general manager that spoke to HoopsHype believes Siakam has a strong case to earn a max extension this summer. “Siakam has a legit case for a max,” he said. “Would I give the max to any of the other players up for extensions? Hell no. I consider these factors: whether the player has an impact on winning, whether he is a great fit for our culture, whether he still has room for growth and whether he can be the best player on a championship-caliber team.”

A Western Conference coach agreed: “With Toronto in the situation that they’re in, no longer having Kawhi Leonard or Danny Green, Pascal Siakam may be a safe bet for them and they may want to give him a max extension to lock him up. I’ve been impressed with his development; he’s improved into a highly, highly serviceable player who’s very efficient and does a lot for that team. From the outside looking in, it seems like he’ll be able to continue his development too. He seems highly motivated and very grateful to be in the situation he’s in and he doesn’t take anything for granted.”

Not everyone HoopsHype spoke to, however, believes Siakam’s case for a max is so open and shut.

“I think they’re going to try to extend him,” one current Eastern Conference GM said. “I haven’t talked to Toronto, but he’s obviously a huge piece for them, helped them win a championship, he’s getting better, he’s young, he’s athletic and he can shoot. They’re going to try to extend him. Do I think he’s a max player? No. Do I think he’s a good player? Certainly. It’ll come down to what he thinks he’s worth, and I’m sure his agents have called around to see what kind of offers he could get if he enters restricted free agency.”

Another Western Conference executive agreed that he’s not worth the max, telling HoopsHype: “Out of Pascal Siakam, Jaylen Brown, Brandon Ingram and Buddy Hield, [the main candidates remaining for a rookie-scale extension], I don’t think any of them will get the max or deserve the max. If I was running each team, I would force them to play it out. In some situations, keeping their cap holds is so much more beneficial. You should only extend if you get a below-market-value deal or if it’s a no-brainer extension.”

Those executives’ viewpoints, that Siakam is obviously deserving of an extension but perhaps not for the max, raises an interesting point. If the Raptors don’t want to give him a max extension, would other teams be willing to do so next summer, when Siakam would be able to hit restricted free agency?

On one hand, Siakam might be relatively young, but, at 25 years old, he’s a decent bit older than the typical player coming off their third season in the NBA. Two of the three players who got signed to rookie-scale extensions this summer are 23 or younger (Simmons and Murray), while the third is LeVert, who is also 25 and didn’t get a max extension.

It’s possible that teams, including Toronto, see Siakam’s age as a hindrance to his upside and believe he might be close to hitting his ceiling.

On the other hand, after the jump the Cameroonian native made from Year 2 to Year 3, going from 7.3 points and 4.5 rebounds nightly to 16.9 points and 6.9 rebounds per game, who’s to say he doesn’t have another level he’s capable of hitting?

Besides increased opportunity and improved ball-handling and finishing, one of the biggest reasons for Siakam’s season-to-season leap was his much-improved three-point shooting. In his second campaign, Siakam averaged just 1.6 three-point attempts per contest and hit a meager 22 percent of them. This past season, the Raptor wing put up 2.7 triples nightly (still not a huge number, but a more confident number of attempts) and hit a healthy 36.9 percent of them.

As long as Siakam can increase the number of outside shots he attempts and maintain around that level of accuracy, he could very well approach 20 points nightly over the coming seasons.

That’s a pretty big if, though, as Siakam will likely never be someone who will hit outside shots off the bounce, which is a skill set every explosive scorer requires.

At the same time, because he can provide so much value in other facets of the game (defensively, he can cover multiple positions at an above-average level; offensively, he’s a terror in transition, can get to the basket in the halfcourt and even create for others), Siakam’s shooting won’t sink him, as long as he can keep hitting shots at a roughly league-average rate.

All in all, Siakam’s offseason will not come down to whether he gets an extension, but for how much that extension is worth. He’s proven he can be a starter on a championship-caliber team, and even if he’ll never be an All-NBA-level guy, he’s the type of productive glue piece that every single coach around the Association would love to have.

If Siakam and Toronto can’t come to terms on a new deal this summer, things could get dicey once the 2018-19 Most Improved Player hits restricted free agency next summer, as another Eastern Conference executive explained to HoopsHype.

“If Siakam doesn’t get extended, he would enter the market next summer where a few teams will have cap space and there isn’t much of a free-agent class,” the exec said. “If [the Raptors] know they want Siakam long-term – and they’re comfortable with how much cap space they’ll have without his small cap hold – they should try to offer an extension just below the max and see if he’s interested in taking it and having that certainty. I think it makes a lot of sense for Toronto to extend him. If they don’t pay Siakam, someone else will – especially in that 2020 market. Restricted free agency is a blessing and a curse because you won’t lose your guy, but it can create bad feelings.”

It would be quite surprising if the Raptors don’t announce an extension for Siakam prior to the start of the 2019-20 season. There’s just too much riding on the marriage sticking together, especially with the departure of Leonard, which could help Siakam reach an even higher level and become the focal point of the next great Toronto team.

HoopsHype’s Alex Kennedy contributed to this report.

You can follow Frank Urbina on Twitter: @FrankUrbina_.