Antetokounmpo remains the white whale for Ujiri, Raptors

TORONTO – For Raptors fans, the 2025 NBA postseason has been a trip through memory lane.

It’s hard not to get nostalgic watching Fred VanVleet hit big shots against the Warriors, OG Anunoby go toe-to-toe with Boston or Pascal Siakam lead his team to the Finals, even if it’s bittersweet to see them do it for other teams. Oh, what could have been.

In fairness, it’s not like Toronto rushed to dismantle that group. If Masai Ujiri and Bobby Webster are guilty of anything, it’s taking too much time to acknowledge that their talented core of championship holdovers was no longer gelling.

Among the reasons they kept it together for as long as they did was the landscape around them. Whenever Ujiri would consider breaking those guys up and hitting the reset button, he would look around the league and see nothing but opportunity. 

We’re living in an era of unprecedented parity across the association – over the next couple weeks, Oklahoma City or Indiana will become the seventh different team to win a title in seven years since the Raptors won it. The East, long been considered the inferior conference, felt especially wide open. 

If you can stay competitive while accumulating and developing talent, you should always be within striking distance of the teams at the top. The right move at the right time could vault you into contention. That’s the way Ujiri saw it then and that’s the way he continues to see it now. And why wouldn’t he? He’s already proven it to be true, albeit under unique circumstances back in 2019.

In the time since he reluctantly launched Toronto’s rebuild last summer and then expedited the process with the acquisition of Brandon Ingram in the winter, the balance of power has become even more imbalanced.

Cleveland, the East’s top seed, is at a crossroads after consecutive second-round eliminations. The reigning champion Celtics, who were already facing a tax crunch and some tough decisions this summer, have lost Jayson Tatum to a torn Achilles. The Bucks are going into the off-season with an injured Damian Lillard and without cap space, most of their draft picks or a clear picture of where their best player stands. The Sixers, ever a wildcard, are coming off a disastrous season and Joel Embiid is coming off yet another knee surgery. Outside of the conference finalists, Indiana and New York, that leaves the likes of Detroit and Orlando – fun young teams on the rise, to be sure, but hardly a murderers’ row.

Once again, opportunity knocks and Ujiri wants to be in a position to take advantage. Over the weekend, on The Hoop Collective podcast, ESPN’s Brian Windhorst identified the Raptors as a team that is “starting to make some noise within the league about looking for a big fish.”

It shouldn’t come as a surprise. This is not the first time that Ujiri’s front office has gone star hunting. There’s a reason why they’re one of the first teams to come up as a potential landing spot whenever a so-called big fish is perceived to be on the block. At minimum, they’ll always make the call to do their due diligence, gauge the player’s availability, and get a price check. Internally, there’s almost always a discussion – is this the right player and is this the right time?

After 25- and 30-win seasons the last two years, the Raptors have essentially put the rebuild behind them. Growth isn’t always linear, and they know that, but with Ingram set to debut as part of a new core group that will earn north of $156 million next season – roughly the value of the league’s salary cap – they expect to take a considerable step forward. The current state of the Eastern Conference allows them to dream even bigger.

Notably, Ujiri is going into the final year of his contract, and with the recent ownership changes at MLSE and the decision to part ways with (and not replace) former Maple Leafs president Brendan Shanahan, you can understand why he seems highly motivated to turn things around quickly.

If he’s looking to make a big splash, this might be the summer to do it. Many league insiders are anticipating an active off-season. This is the calm before the storm, with the June 25 draft considered to be a major inflection point. With several underperforming teams in need of a shakeup, there could be multiple star players on the move.

After a brief resurgence in the loaded Western Conference, the Kings are back in no-man’s land. They’ve got an all-star centre in Domantas Sabonis to shop, as well as former Raptor DeMar DeRozan and the recently acquired Zach LaVine. The disappointing Suns have made three coaching changes in three years, so, naturally, there are eyes on Kevin Durant and Devin Booker. Jaylen Brown is a name to watch if the Celtics decide to switch gears. It feels like Utah has been flirting with the idea of moving Lauri Markkanen for years. Is Cleveland ready for a change? How about Memphis or Atlanta (who just replaced its general manager)?

Then there’s Giannis Antetokounmpo, who has been perpetually linked to the Raptors.

First, pump the breaks. 

If you’ve been on the internet over the last couple days, you’ve probably seen a report citing “mutual interest” between Antetokounmpo and Toronto. It’s not a report, so to speak. It’s an aggregation. Aggregation is common in this business but it’s often misleading because it takes a piece of information, consolidates it into a headline, and strips it of context.

The context, in this case: In his weekly mailbag column, venerable Toronto Star beat reporter Doug Smith was answering a fan question about the likelihood of the Raptors acquiring Antetokounmpo in a trade. It was the fourth item in the column, sandwiched between a question about Shai Gilgeous-Alexander’s case as the NBA’s best Canadian player ever and television coverage of the Conference Finals. Hardly the packaging for breaking news, but it’s taken on a life of its own on social media.

“I don’t know if it will happen but I do know there is mutual interest between Antetokounmpo and the Raptors,” he wrote. “The wild card is cost.”

There’s always been mutual respect between Antetokounmpo and the Raptors. Could you also call it mutual interest? Yes, that would fit too. 

Certainly, it’s been well documented on the team’s side. Ujiri has been chasing Antetokounmpo since his first year in Toronto, when he tried desperately to trade into the 2013 draft only to watch Milwaukee select the raw prospect from Greece with the 15th-overall pick. From the moment Kawhi Leonard left in the summer of 2019 until Antetokounmpo ultimately signed his extension with the Bucks 17 months later, every decision the Raptors made – big and small – was made with him in mind. The plan was to create and maintain enough cap space to make a run at the superstar forward in the summer of 2021, when he would have become a free agent. So, yes, they’re very interested.

As for Antetokounmpo, it’s worth noting that he and his family have a long-standing relationship with the Raptors president and vice chairman, who helped them get Greek citizenship. If Antetokounmpo had hit free agency in 2021 and if he decided to leave Milwaukee, multiple league sources close to the Bucks star believe that Toronto would’ve had as good a chance as anybody. The sense is the same holds true today. If Antetokounmpo is made available, the Raptors would surely be in the mix.

But is he available? The entire league, not just the Raptors, is waiting on pins and needles to find out. The Bucks are in disarray, without the resources required to get out of it, so few would blame Antetokounmpo for deciding it’s in his best interest to move on. That said, he’s fiercely loyal. He’s also a professional and very private person, so however this plays out, it’s unlikely that it plays out publicly in the way that it would with several other stars of this era.

That is the first of many variables that will determine Antetokounmpo’s future. The Bucks might also be better off moving on and recouping some of the assets and draft capital they’ve lost over the years, and you could make that argument, but it’s hard to see them trading a generational talent until and unless he wants out.

Let’s play out this hypothetical scenario, where he asks for a trade. They could honour his request and send him to his preferred destination, purely from a sense of loyalty, but with Antetokounmpo under contract through 2026-27, it would behoove them to gauge the market, create a bidding war, and ultimately accept the most lucrative offer. 

The Raptors are well positioned to put together a compelling offer, but the pertinent question is whether they would be willing to include Scottie Barnes. On one hand, the organization believes wholeheartedly in the 23-year-old former fourth-overall pick, Rookie of the Year and all-star. They’ve committed to him, to the tune of a $225 million max contract extension. They declined to make him available in trade talks for Durant during the summer of 2022, and he’s their only player that has consistently been off limits. On the other hand, this is Antetokounmpo – a top-three player in the league, two-time MVP, NBA champion and Ujiri’s white whale.

If it comes down to it, it’s safe to say that any preliminary offers from the Raptors wouldn’t include Barnes. They would almost certainly try to get it done with a package of picks, prospects, and salary filler, not unlike the deal they offered Portland for Lillard in the summer of 2023. Would something like, say, RJ Barrett, Jakob Poeltl, Gradey Dick or Ja’Kobe Walter, and a handful of future first-round picks be enough to entice Milwaukee? Probably not, especially considering the Bucks don’t own their own picks and aren’t incentivized to completely bottom out. Assuming their plan is to remain competitive, and they intend on negotiating with more than one team – hello, Dallas – there are a bunch of clubs that could easily top that offer; Houston, San Antonio, and Orlando, just to name a few. Unless, of course, Barnes is on the table. 

Again, lots of variables, not the least of which are Antetokounmpo’s uncertain – or at least unknown – intentions. Could he end up in Toronto? It’s not impossible, but for now, it remains little more than a pipe dream. What we do know is that the Raptors are lurking because they’re always lurking. The clock is ticking on Ujiri’s contract, and perhaps his iconic tenure. Will he take a big swing this summer? If there’s a way of landing his man and delivering on his long-standing promise to the organization and its fan base – “We will win again in Toronto” – rest assured, he won’t strike out looking.