So, where do the Raptors go from here? 

It turns out Giannis Antetokounmpo likes breaking hearts just as much as he likes breaking rims.

The 26-year-old Nigerian phenom signed a 5-year supermax contract extension worth $228.2 million on Tuesday, making him the highest-paid athlete in NBA history. The extension marks the latest peak in a remarkable journey that took Antetokounmpo from the streets of Athens, Greece to a two-time MVP idolized by children throughout the world. It also means Antetokounmpo will remain a Milwaukee Buck until at least 2025 — should he not get traded (he has a player-option on the final year and a 15 percent trade kicker throughout, per Shams Charania) — and therefore not become a Toronto Raptor, as many fans hoped. 

The deal comes as a surprise to many around the league who thought that Antetokounmpo might hold off on signing a deal and instead become a free agent next offseason, when teams like the Raptors, Miami Heat, and Dallas Mavericks were thought to have a chance at landing him.

It is no secret that Antetokounmpo was the Raptors’ No. 1 target next offseason. The Raptors prioritized cap flexibility for the past two years in the hopes of signing a max free agent in the once-loaded class of 2021, letting Marc Gasol and Serge Ibaka walk after only offering them one-year deals this offseason. In fact, Raptors’ President of Basketball Operations Masai Ujiri has a longstanding relationship with Antetokounmpo: he helped his family secure Greek visas after migrating there illegally from Nigeria and has become a role model for Antetokounmpo since he was a teenager.

The Raptors even made a point of letting their longtime fascination with Antetokounmpo be known in a recent episode of “Open Gym,” going out of their way to include a clip of the Raptors’ front office trying to trade up for Antetokounmpo in the 2013 draft.

https://twitter.com/TSN_Sports/status/1336870799236534272

Ante-Toronto is officially dead, however (for now), and so Ujiri and Co. will have to figure another way to lead this Raptors team back to championship contention. The core is set: Pascal Siakam (26), OG Anunoby (23), and Fred VanVleet (26) are all entering the primes of their careers and will likely be Raptors for a long time. 

But what can the Raptors do to give themselves the best chance at competing for a title in the coming years while their championship window is still open? Let’s explore some options. 

Extend OG Anunoby

Anunoby is extension-eligible until December 21st. The 23-year-old forward is coming off the best season of his career where he averaged 10.6 points, 5.3 rebounds, and 1.6 assists on 51/39/71 shooting. He also got better as the season went along, tightening his handle and becoming more comfortable putting the ball on the floor to create his own shots, leading to a break-out series against the Boston Celtics.

Anunoby is exactly the type of versatile wing/forward that modern NBA teams covet because he can guard every position on the court including point guards and centers, making him versatile enough to play in almost any lineup, anywhere from the two to the five. 

The Raptors were most likely not going to extend Anunoby before the season prior to the Antetokounmpo signing because they were prioritizing maintaining a max cap-slot next offseason, but they might want to reconsider now that Antetokounmpo is off the board. While there are still many solid free agents remaining (which we will get into later), the only surefire max free agent is Kawhi Leonard, and a reunion with The Claw seems unlikely, so the Raptors could hypothetically eat into that max slot by extending Anunoby. 

The Raptors’ frontcourt depth took a big hit this offseason with Gasol and Ibaka leaving, meaning Anunoby is primed for a breakout season. He will likely have a much bigger role on the team on both sides of the floor and could become a very costly player if he excels in that role (think $22-25 million per year), which is why the Raptors should consider locking him up before the season starts for something like $80 million over four years. It could save the Raptors a lot of money in the long run and give Anunoby the safety net he might desire.

However, the Raptors might want to maintain cap flexibility next offseason, and extending Anunoby for anywhere over $18 million per season makes a max cap slot much more complicated. Why might the Raptors want to maintain a max cap slot now that Antetokounmpo isn’t coming, you ask? Because the 2021 free-agent class has plenty of other helpful players, and the Raptors are optimistic that they can become the free-agent destination that no one else thinks they can be. 

2021 Free Agents

Even with Antetokounmpo off the board, the Raptors’ plan to maintain cap flexibility still makes a lot of sense. After all, the 2021 free-agent class is full of good players who fit the Raptors’ identity and would make sense for the right price including Jrue Holiday, Rudy Golbert, Victor Olidipo, LaMarcus Aldridge, J.J. Redick, PJ Tucker, and many more.

Here, however, is where a lot of peoples’ opinions of the Raptors as a free agent destination vary. The Raptors have never been able to land major free agents in their 25-year history. Many fans think that this is still the case: that no free agents want to come to snowy Toronto, Canada. But Ujiri and Co. are optimistic that the opposite is true: they believe that the Raptors have positioned themselves as an attractive market for players who want to win. They have a history of developing talent and their core has proven that they can fit around a superstar (hello Kawhi Leonard) and win (hello Larry O’Brien). 

The Raptors could try to re-sign the GROAT Kyle Lowry along with a solid free agent or two, building around the core with high IQ players who can ideally play on both sides of the ball. The Raptors will have a much better idea of how close they are to championship contention after this season, when their core players will have a chance to show exactly how big of a load they can efficiently carry.

There’s also the case of the only surefire max player remaining in 2021: Kawhi Leonard. While it seems unlikely that Leonard would return to Toronto, he might look to move on from the Clippers if they flunk out of the playoffs two years in a row. Leonard wanted to go home, but he also values winning. There is a chance he comes to the conclusion that he made a mistake by going to Los Angeles and leaves for a franchise that he knows he can win.

I would be shocked if Leonard came to Toronto, but the Raptors have positioned themselves as a solid free-agent destination, nonetheless.

Trade Market

Time to have some fun.

The Raptors have several expiring contracts this season including Norman Powell (player-option), Chris Boucher (non-guaranteed), Aaron Baynes (non-guaranteed), Stanley Johnson, Patrick McCaw. Terence Davis, and Kyle Lowry. They also have all of their future first-round picks. If they want to get aggressive on the trade market ahead of the February 6th trade deadline, they can.

Whether the Raptors are buyers or sellers at the deadline will depend on a lot of things: how well they are playing, how good the rest of the Eastern Conference looks, the market for their assets, and who is available to trade for.

One option that makes a lot of sense is to try to retool through the draft, trading off expiring assets like Powell, Boucher, and Davis to get first-round picks that they can quickly develop into future contributors (like ROTY-hopeful Malachi Flynn). However, if it turns out that the Raptors are close to contention now, that strategy might be too long-term for them. 

Another option — a more exciting one — is to buy. I’m not sure if you have heard, but James Harden is available. Yes, the Harden that’s one of the greatest and most unguardable scorers of all time. That one.

If Harden’s market depreciates to the point where the Raptors can get him for Lowry and picks or, if they wait until the trade deadline, VanVleet and picks, they should jump on that opportunity. Superstars like Harden very rarely become available. You might not like how he plays, and he might have trouble adjusting to a system that isn’t all about him, but Harden is an offense onto himself and has shown a willingness to not want the ball in his hands all game. If you can surround Harden’s offense with defensive-wings like Siakam and Anunoby, the Raptors could give themselves a good shot at winning a title despite shortening their contention window (Harden has two years left on his deal).

Wild speculation thinking of the day: Houston will almost certainly try to keep Harden for this year, but if they are looking to move him, there are three ways I could see the Raptors making an offer on him.

— Daniel Hackett (@dhackett1565) December 3, 2020

Even if Harden’s price point is too high, there will be other players that will become available that the Raptors can try to pursue.

Rudy Golbert is yet to sign a contract extension with the Utah Jazz. Ditto for Victor Olidipo and the Indiana Pacers. If you want a more cost-controlled asset, what about a guy like Wendell Carter Jr. on the Chicago Bulls? Or John Collins with the Atlanta Hawks?

The point is, the NBA in constant flux, with different players always being made available in trades. If the Raptors are willing to sacrifice future cap space now that Antetokounmpo is off the board, they could get aggressive in the trade market, one way or another.

Front Office

As long as Masai Ujiri and Bobby Webster remain in the Raptors’ front office, there is no reason to be pessimistic. However, both of them are on expiring contracts, and while Ujiri said that his “staff” is almost all signed, he said there was no timetable for his new contract with MLSE.

Ujiri is the best executive in the NBA. As long as he is leading the Raptors, they will remain competitive and eventually take that next step towards contention through internal development and savvy moves: Ujiri has demonstrated that he is bold enough to go after superstars when the opportunity arises. He has shown the ability to draft gems in the late first round of the draft and has developed all types of talent.

This is a person who drafted Pascal Siakam 27th overall, after all. Recency bias might have you down on Siakam, but appreciate that the Raptors have a 2nd-team all-NBA forward who has taken dramatic steps forward each season who is just now entering his prime. Is he an efficient No. 1 option on a title team? The jury is still out on that. But Siakam is elite and still getting better.

While it’s nice to hypothesize about Anunoby’s handle or VanVleet’s floater, Siakam is already an elite two-way player with a growing array of moves. And while Raptors’ fans tend to devalue scoring despite the current iteration of the team needing it so badly, Siakam is the one guy on the team who has proven to be somewhat efficient while carrying a big load, doing so in just his first try as a No. 1 option. 

Raptors’ fans still have a lot to be optimistic about despite Antetokounmpo’s extension. Don’t let the dark days of Raptors’ past bog you down: the franchise has turned a corner and has kept their options open for the future. And there are plenty of options still available.