What Will the Toronto Raptors Do in 2020 Free Agency?

Adon Moss
7 min readNov 20, 2020


In seven hours from the time I write this, the NBA Free Agency shopping spree commences. And if the last week is a predication of what is to come — get your popcorn and head to your bunker because there’s about to be an downpour of Woj bombs.

When it comes to the Toronto Raptors, though, I suspect a much more mild experience.

A couple of reasons why.

  1. The Eastern Conference Arms Race has Begun

Granted the bottom half of the East is utterly pathetic, again. But the big boys at the top are going full steam ahead.

Milwaukee launched first with two convince-Giannis-that-we-will-do-anything-to-keep-you-here trades — only to have one of those trades voided or rescinded or pretended-it-didn’t-happen. It remains, suspiciously, unclear. Nonetheless, the Bucks landed Jrue Holiday and will likely grab another win-now piece with another (the same?) sign and trade.

Then Brooklyn started getting all crazy with James Harden trade talks — a product of his summer hang-outs with Flat Earther Denier Kyrie “everyone’s a coach” Irving and Twitterverse Star Kevin “I don’t need no burners” Durant, and of his contempt for the Houston Rockets’ Trump-loving Governor.

While having three high usage dudes like that on one team would be…uhh…difficult — that is a scary-ass Big Cranky Three. It could also be the ultimate, super duper fun reincarnation of the Seven Seconds or Less with Steve Nash and Mike D’Antoni at the metaphysically-shared helm. Brooklyn has already traded for sharpshooter Landry Shamet and is likely to continue to upgrading their assets as their window to win opens now.

As expected, Philadelphia immediately got funkadelic on the trade floor by shipping misfits (I say that kindly) Al Horford and Josh Richardson out and bringing Danny Green, Terrence Ferguson, and Seth Curry in. The Godfather of The Process, Darryl Morey, (Sam Hinkie’s idea of you only win with superstars so you tank and tank and tank until you unearth a superstar is an offshoot sect of Darryl Morey’s you-only-win-with-superstars cult), loves to hustle and bustle until he maximizes his superstar potential. We saw him do it many times over for Tracy Mcgrady/Yao Ming and for James Harden and there’s no reason to think he won’t continue to manipulate Philly’s roster until Ben Simmons and/OR Joel Embid’s talents are optimized. So LOOK OUT!

Without a doubt, Miami and Boston also believe they are in win-now mode too. It is only a matter of time until they move to bolster their rosters.

And don’t forget the sweet old mid-western town of Indiana. The Pacers are at somewhat of a crossroads, but, as currently constructed, remain feisty.

2. Giannis Antetokounmpo is Staying Put?

Milwaukee went all-in for GA by sending out a bevy of first picks for Jrue Holiday and, essentially, Bogdan Bogdanovic. It is absolutely the trade you do to convince your superstar talent to stay. And, to be honest, it kind of feels like that’s what Giannis is going to do.

The Bucks probably don’t do these trades without some kind of reassurance of Giannis. Not to mention, Bog Bog is good friends with Giannis too.

Giannis has also proven he is his own archetype. He doesn’t have an AAU or USA Team Basketball crew. Instead, he wants to pour milk on them all, crunch’em up and swallow them all down like a bowl of fruit loops. His mentality says: I do not need to go team up with other superstars (Luka Doncic or Jimmy Butler and the Gang or our hallowed Toronto Raptors) to win. I will prove that I can do it here in the Land of Cheeseheads.


If that is the case, then Masai Ujiri’s dream of recruiting Giannis in 2021 disappears. His timeframe and framework, then, extends further out. He is no longer rushed to build an attractive team in order to lure Giannis from other suitors.

3. No Toronto, No Fans, No Rush

The 2020 NBA season is going to be as unpredictable and unusual as everything else in life in the Pandemic era. For Toronto, this is especially true. The team is likely to have its home arena somewhere in the United States for travel reasons — props to Canada for being…safe. But even if they were to play in Toronto, there would be zero fans. If there was a year to dissatisfy your fan base it would be in a year where selling tickets was irrelevant. It’s a GM freebie. Kind of.

4. Rebuilding the Plane while Flying It

The Raptors are as close to rebuild as it comes. Their mainstays are aging or trying to get paid. Their core is young: the Batman, Pascal Siakam, is 26 and his soon to be Robin, OG Anunoby, 23. Fred Van Vleet has already made it clear that he wants to get paid. And while he is worth a chunk of change, a younger team with more cap space (like New York or Detroit) may offer him a bit more than Masai thinks he is worth. All the power to FVV, but Toronto likely moves on.

So Free Agency

With a financial downturn, a top-heavy East, a fanless, shortened season, and a fledgling new Raptor era, it feels like a year where Masai the Oracle makes some of his famous prognostications by finding value-around-the-edges and, perhaps, making a couple of small taking-candy-from-a-baby trades with teams voraciously desperate to win or shake things up. Though these may happen at the trade deadline if Toronto waits to see where it sits in the playoff-picture.

The only caveat to everything that I have said is Toronto truly thinks it can get out of the east this year. That solely depends on Siakam’s strides as a first-option and OG’s development as secondary creator. I don’t think they are there yet.

Peripheral Acquisitions

They have to fill out a roster regardless. And now is the time to do what Toronto so famously does: grab guys the league is out on or was never in on, and see if they can Rumpelstiltskin them into gold. They did this with FVV, Siakam, Bismack Biyombo, James Johnson, PJ Tucker (a bit), Chris Boucher, and Rondae Hollis-Jefferson. All guys who, at one time, were young, athletic, hard-working, or all of the above.

Names to look out for:

Harry Giles. Bobby Portis. Noah Vonleh. Michael Kidd-Gilchrist. Thon Maker. Glen Robinson III. Emmanuel Mudiay. Nerlens Noel. Deandre Bembry. Gary Clark (RFA). Tremont Waters (RFA). Denzel Valentine (RFA) Bruno Cabocolo (JOKING!).

It’s a trade, but getting something for FVV’s departure through a sign and trade feels right. Ignas is Canadian(!) and Franky Smokes is a raw athlete that SCREAMS the need for the kind of nurturing and development the Raptors can provide.

Young Upside More Expensive Signings

If Toronto wants to start pairing guys with Pascal and OG that are similarly up-and-coming and of the same age, Masai may look to find some value in the market. There are not many this year.

Names to look for:

Christian Wood. Malik Beasley. Kris Dunn.

A Devilish Deal by the Master Himself

If the Raptors were to take one more swing at the fences to honour Lowry’s possible crowning year then perhaps they resign Serge Ibaka to an expensive one-year contract (unless he’s the one traded) and make one of the following deals:

Victor Oladipo is expiring, disgruntled, and still having to prove he can return to form from a major injury. Sounds like a similar situation from not toooo longgg agggooo…If he does return to form, he is a two-way monster. If he doesn’t Toronto’s losses are minimal.

If Harden goes to Brooklyn, Spencer Dinwiddie is likely in that package. If not, the Brooklyn Nets may look to spend more on a shooting big. A sign and trade for Serge Ibaka gives Toronto a downward-trending prospect in Rodions Kurucs and a fairly-paid, dynamic replacement for FVV and complement to Lowry with Spencer Dinwiddie.

Okay, okay, okay. Before you get all up in arms about it. Hear me out. Awkward? Probably. Improvement? A bit. Nostalgic? Yes. Storybook ending? Absolutelllllly!

The thing is, there’s not much out there if Toronto is “swinging for the fences” for only one year. Guys are either on big, long contracts or not going to move the needle much. In this trade you melt Raptors fans’ hearts, you get Lowry’s bestie back for his final adieu, you redeem Masai’s betrayal, you get a creator who can take the load off of Siakam and Lowry, and you get a humbled dude — I think — who will understand that his role is subsidiary to the youth movement. Besides, I liked him running point forward for the Spurs in the bubble. He can be a great facilitator off the bench, if he accepts it.

Whatever happens in seven hours, trust that somewhere up Masai Ujiri’s sleeve is the plan to lead the Toronto Raptors into the glorious future.



Adon Moss

Policy Analyst; Strategic Foresight Analyst; Freelance writer; Basketball Opinionist.