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Josh Lewenberg

TSN Raptors Reporter


TORONTO – On Tuesday night, the eve of the NBA draft, most of the league’s executives will fall asleep with visions of big boards and prospect rankings in their heads.

By this point, they’ve probably zeroed in on a player or two. They know who they want and they’ve convinced themselves that their guy is the right guy – the franchise cornerstone, the diamond in the rough, or maybe if they’re lucky, a future superstar or generational talent.

How do they get their guy? Will he fall to your team or do you have to trade up to land him? Okay, maybe they’re not sleeping much after all.

It’s easy to talk yourself into and become infatuated with a prospect’s upside at this time of year. Everybody is ‘ the next LeBron James’, or ‘the next Kevin Durant’, or ‘the next Kawhi Leonard.’ Most of them won’t be, of course, but every once and while the stars align.

Imagine what it must feel like when your guy actually turns out to be the guy. Now, imagine what it must feel like to miss out on him.

In his time as a lead exec, both with Denver and Toronto, Masai Ujiri has had plenty of success on and around draft night. He’s found quality NBA rotation players, built a championship core, and even plucked an unlikely all-star – Pascal Siakam – from the bottom of the first round.

However, the 2013 draft – his first at the helm of the Raptors’ front office – almost certainly stands out in his mind. That’s the night he missed out on Giannis Antetokounmpo.

Ujiri isn’t the only one that missed out, to be fair. So did 28 other clubs. But Masai was pining for him before most of them – before Giannis was the Greek Freak, and long before he was a two-time Most Valuable Player.

Toronto didn’t have a pick that year but Ujiri tried desperately to trade into the draft in the hopes of selecting Antetokounmpo – the mysterious, long-limbed prospect from Greece. Giannis was on the draft radar, but he was far from a sure thing. Most teams didn’t know what to make of him, some didn’t even know much about him, but Ujiri had done his homework and believed that he could be special.


Alas, Ujiri couldn’t swing a deal and Milwaukee took Antetokounmpo with the 15th-overall pick.

Now, more than seven years later, the Bucks and their franchise player have reached a crossroads, and Ujiri – like the rest of the league – is paying close attention.

Antetokounmpo is eligible to sign a super-max extension with Milwaukee – worth up to $244 million over five years – this off-season. He has until December 21 – the eve of opening night – to sign it. If he doesn’t, he’ll be a highly coveted unrestricted free agent after this season. At least a third of the league’s teams have spent years planning for the summer of 2021, with the mere possibility that a player of Giannis’ calibre could be hitting the open market.

After flaming out of the playoffs, yet again, this past fall, Antetokounmpo was forthright with his intentions, both privately and publicly. For him to commit to the Bucks long-term, they would have to prove that they’re serious about contending for championships, and they would have to do it fast.

Apparently, they heard him loud and clear. According to reports, the Bucks are acquiring point guard Jrue Holiday from New Orleans for a haul that includes three future first-round draft picks and the right to swap two additional future picks. (They’re also reportedly landing sharpshooter Bogdan Bogdanovic in a sign-and-trade deal with Sacramento.)

In a vacuum, it’s a bad and potentially franchise crippling trade for Milwaukee. Holiday is a very good two-way player and he’ll be a clear upgrade over Eric Bledsoe, who is heading back to the Pelicans in the deal. Still, that’s a hefty price for a non-superstar – a guy that helps but doesn’t move the needle like, say, Chris Paul (who Phoenix got from Oklahoma City for one first-rounder and a collection of role players earlier on Monday) would have.

But context matters. If Milwaukee’s recent roster makeover is enough to convince Giannis to stay, it’ll be well worth it. Antetokounmpo is arguably the best in the game, at worst he’s a top-three player, and he’s about to turn 26 and hasn’t yet entered his prime. Those guys are hard to get your hands on. When you do, you’ve got to do everything you can to hang onto them, especially if you’re a small-market team.

According to sources, the sense around the league is that the Bucks wouldn’t have pulled the trigger on Monday’s moves without assurances that Antetokounmpo plans to commit to Milwaukee long-term and sign an extension over the coming weeks.

Assuming that’s the case, it’s a disappointing turn of events for the Raptors and any of the several other teams that hoped to make a run at the Bucks’ superstar in free agency next summer. With that said, even if Giannis is off the board, that shouldn’t change Toronto’s plans.

The Raptors haven’t had significant cap space, or the ability to chase a big-name free agent, since they signed DeMarre Carroll to an ill-fated four-year $60 million deal in 2015. Once Leonard left for the Clippers in free agency a couple summers ago, Ujiri set his sights on 2021, when most of the team’s big contracts were set to expire. That this timeline aligned with Antetokounmpo’s possible free agency wasn’t a coincidence, but they haven’t put all their eggs in the Giannis basket.

Regardless of whether the Greek Freak is available, there’s value in having cap space. Next summer’s free-agent class should still be loaded and could include Leonard, Paul George, Rudy Gobert, Victor Oladipo, Paul, Blake Griffin and former Raptor DeMar DeRozan. With cap flexibility they could also absorb a big contract in a trade. Or, if they don’t like anything on the trade or free-agent markets, they could opt to re-sign Kyle Lowry – who will also be unrestricted – and the rest of their own guys. It gives them the option to pivot in one of several different directions.

The goal when free agency opens this coming Friday at 6 p.m. – and when players are officially allowed to sign new contracts Sunday afternoon – likely remains the same.

Toronto’s top priority will be to retain Fred VanVleet – arguably the best player on the market – but do so at a cost that will allow the team to maintain its coveted cap flexibility for next summer. If a team, likely the Knicks or Pistons, make a big offer – and Antetokounmpo is indeed off the board for next year – perhaps the Raptors are more inclined to spend a bit more to match or compete with it. However, this will still be a balancing act.

League sources still consider the Raptors the frontrunners in the VanVleet sweepstakes. They’ve built a strong relationship and mutual respect over the past four years, and they understand each other’s short and long-term ambitions, which is important going into any negotiation.

But it’s clear VanVleet – a savvy businessman, who has earned the right to seek the significant pay raise he’s worth – won’t take a substantial hometown discount to stay in Toronto, and the Raptors know that. It will come down to whether they’re able to find a number – and term – that makes senses for both parties. The good news for Raptors fans is that both player and team seem highly motivated to find that number and move forward together.


“We’ve said it publicly, privately, every which way, he’s our top priority,” Raptors general manager Bobby Webster said of VanVleet over a videoconference on Tuesday evening. “The biggest priority for the off-season is bringing him back. We’ve had a great run for four years and we fully expect that to continue, and everything’s been positive.”

Although reports of Marc Gasol’s departure from the NBA were premature, the veteran centre appears primed to finish his career back home in Spain. If that’s the case, re-signing Serge Ibaka – and perhaps Chris Boucher, a restricted free agent – should become an even bigger priority.

Ibaka will be in high demand. Reported interest from contenders like the Lakers, Clippers and Nets shouldn’t come as a surprise. Those teams would love to add a quality veteran and NBA champion, who is coming off a career year, but here’s the catch: they can’t offer more than the smaller mid-level exception, south of $7 million annually.

Is he willing to take a big pay cut to chase another ring? Would he join a younger rebuilding club that can give him more money and longer term? Or, will he choose to stay with the Raptors, who’ll likely make a generous one-year offer, but (outside of VanVleet) probably can’t commit long-term money?

Once the dust settles on the draft and free agency, the Raptors have another big decision to make, and one that should be even more telling in terms of their plans for next summer.

OG Anunoby is eligible for a rookie scale extension up until the start of the regular season. If they extend him now they can probably do so at a more reasonable cost than if they wait and let him become a restricted free agent in 2021.

The benefit to waiting – and it’s significant – is he would only be on the books for his cap hold of $11.62 million, which could allow Toronto to use their space before re-signing Anunoby (or matching any offer sheet he signs).

The Raptors have plenty of business to attend to over the coming weeks. All the while, they’ll have an eye on the developing situation in Milwaukee. Whenever he makes it, Antetokounmpo’s decision will send shockwaves around the league. The question the Raptors – and several other teams – face is how much they let it affect the important decisions that they have to make.​