If Raptors could have nabbed third pick at NBA Draft for Siakam, they could regret not acting

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Patience can be a virtue, but too much of it can become a hindrance.

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Time will tell if the latest bit of rumoured transactional restraint by a front office that has become synonymous with studying its cards for ages before making a move will come back to bite the Toronto Raptors.

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In a Wednesday piece centred on the Portland Trail Blazers and recent trade options either to surround Damian Lillard with more talent to keep him happy, or start a rebuild there, ESPN senior NBA writer Zach Lowe got many worked up with the line: “The New Orleans Pelicans and Toronto Raptors weren’t ready on draft day to pivot away from Zion Williamson, Pascal Siakam or O.G. Anunoby, sources have said.”

Lowe continued: “Williamson is a franchise-changer when healthy, but he’s rarely healthy. Siakam and Anunoby are very good — Siakam is an all-star — but would either have vaulted Portland into the ring of championship favourites.”

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Putting aside whether or not Portland benefitted by not making a major move and thus resulting in Lillard asking for a trade, it’s worth analyzing the fallout for Toronto.

Masai Ujiri, Bobby Webster and the rest of the Raptors braintrust are currently in a similar, though less advantageous position as the Blazers. They are also caught between two timelines — one centred around 21-year-old former rookie of the year Scottie Barnes, this year’s 13th overall selection Gradey Dick and the still-young-enough Anunoby, and another where they need to find a way to make Barnes and Siakam excel together while on the court, while also keeping in mind Barnes will be entering his athletic peak long after Siakam’s has vanished.

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It’s easy enough to say not getting Scoot Henderson and whatever cap-filler was necessary for Siakam or Anunoby at the June 22 draft could set the Raptors back significantly, but that line of thinking would be making a lot of assumptions.

One: That the Raptors knew Fred VanVleet would be leaving for Houston about a week later. That’s not the case. The Raptors expected VanVleet would be back all season long and, really, until James Harden-to-the-Rockets went up in smoke, they were right to think they had the upper hand.

With VanVleet back, Siakam likely would have been signed to an extension and the team would have run it back, with Dick, a healthy Otto Porter Jr. and a free agent or two added as well.

Even if you believe that team isn’t scaring any contenders, it was a clear path to take. VanVleet later leaving changed the equation and made Siakam sticking around less sensible.

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Plus there’s the important fact that nearly until Charlotte stepped up and made the second pick of the draft, it wasn’t guaranteed who the Hornets would take. While Scoot Henderson would have been a fantastic fit in Toronto as its new lead guard, there was still a good chance Charlotte would have taken him, leaving Portland to decide on Brandon Miller or Amen Thompson.

Miller and Thompson have significant upside, like Henderson, but many don’t see quite the same upside as with Henderson, who could have gone first overall in many previous drafts.

Miller or Thompson would have been nice in Toronto, but in exchange for Siakam, the two-time all-NBA performer who has proven to be one of the 20 best players in the league? Maybe not.

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Without knowing for sure Henderson would be available from the Blazers, it would have left little time to make the important call on a deal once the Hornets opted for Miller.

It also feels a bit unlikely that Anunoby would have been enough to pry away the third pick, even if Toronto took on centre Jusuf Nurkic’s contract in the process. But what if Anunoby for 20-year-old London, Ont., native Shaedon Sharpe and 23-year-old scoring guard Anfernee Simons was an option?

While Anunoby is still young enough (he turns 26 next Monday) and different enough than Siakam (Anunoby is an elite catch-and-shoot three-point shooter and an even better defender, though not as good as Siakam at nearly everything else), Simons and Sharpe might be more viable long-term plays around Barnes.

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Toronto would have been trading one of the premier defenders in the NBA for a deadly scorer who can’t defend at all in Simons, and another minus defender in Sharpe, who does has big-time upside as a shooter and scorer and is one of the best athletes in the league.

Anunoby for Portland’s pick and Simons probably would have been a realistic option, should Toronto have wanted to do it, had the Blazers stayed put at five in this draft (or even fallen to six or seven), which is where they were before getting lottery luck on May 16 and leaping up to No. 3.

As enticing as Thompson and other prospects are, Henderson and Miller were seen by most as a tier above the other prospects in this draft, other than no-doubt top pick Victor Wembanyama. Portland would have been more willing to deal a prospect who wasn’t Henderson or Miller.

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But, again, Toronto has always been sky-high on Anunoby (before Siakam broke out in the championship season, the team actually expected Anunoby to become the far superior player) and hopes to keep him around long-term.

So, what now? Not making a deal either at the trade deadline or the draft has complicated a potential Siakam deal and that grows all the time with Siakam inching closer to unrestricted free agency by the day. If a team acquires Siakam this off-season, it won’t be allowed to extend him for six months. That would mean either Toronto gets less in return, given the new team’s uncertainty about a long-term commitment, or Siakam would have to verbally promise to sign when eligible to maximize Toronto’s return.

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The Raptors could sign Siakam themselves anytime for four years and $201 million, if he’d agree and abandon the chance he makes another all-NBA team, which would significantly increase how much he’d be eligible for next summer, per the NBA’s collective bargaining agreement which rewards top players.

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At this point, given any shot at Henderson has passed, coming to terms on an extension with Siakam seems like the best move the Raptors could make. It isn’t easy to come across players as good as Siakam. He’s still by far the team’s top player and he also wants to remain in Toronto.

They could test out ways to make the Barnes-Siakam-Jakob Poeltl front-court viable offensively (a challenge, given Poeltl is a complete non-threat outside of the paint and the other two are well-below-average from beyond the arc).

If it’s clear it’s not going to work, they’d be able to get a lot down the line for a Siakam signed to a long extension.

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