Which Raptors season deserves a “The Last Dance”-style documentary?

Multi-part documentaries are all the rage, and now they’ve infiltrated the NBA, thanks to ESPN’s The Last Dance, the 10-part series that breaks down the end of the 1990s Chicago Bulls dynasty.

Since we all have lots of time on our hands to daydream, I can’t help but wonder: Which Raptors season would make a good multi-part documentary series?

The Last Dance, of course, seeks to capture more than just what happened on the floor; it’s a look “behind the curtain” at the players, personalities and subplots that make up a team and a memorable season. So our Raptors doc would have to be the same: you’d need a great backstory, some cool unknown stories, some villains, some twists and some larger-than-life people to make it interesting.

Given the short history of the Raptors, it wasn’t too difficult to narrow down the options; really, the only four candidates are the four main eras of Raptors basketball; we can call them The Isiah Years, The Carter Years, The Bosh Years, and The Lowry Years.

Let’s look at the following categories for each of these eras, and provide some ranks on a scale of 1-10, and add ‘em up to see which era would make the best docu-series, for a final score out of 70. (For the purpose of this exercise, we’ll assume that we get full co-operation from all the relevant people involved each era.)

• Main plot: The “A” plot of the The Last Dance is the Jordan-era Bulls and their last title run. What is the main story driving our Raptors documentary forward, and how compelling and interesting is it?
• Focal point: The 1997-98 season is the focal point of The Last Dance; it grounds everything and all of the storytelling works back from there. What is the focal point of our Raptors documentary, from which our story flows?
• “B” Plots: What are the cool and interesting mini-stories that come out of the doc, that are connected to the main plot, but don’t necessarily drive it? Think about Jordan punching Steve Kerr, or Pippen refusing to re-enter the Knicks game, or Jordan’s “gambling problem.”
• Personalities: Jordan is an interesting guy. Phil Jackson and Dennis Rodman sure are too. Scottie Pippen has a great backstory, and there are plenty of interesting side characters, from Jerry Krause to Scott Burrell to Charles Oakley. So for our Raptors doc, who’s gonna be good on camera, who do people want to get to know more, who’s got great stories to tell?
• Background: The Last Dance has taken us back to the early days of all the main players and personalities of the 1990s Bulls, and to the history of team itself. If we travel back with our Raptors personalities, are the stories deep and interesting enough to sustain interest?
• Villains: Even a good doc needs a counterpoint! Jerry Krause and Bulls management provide the blueprint, so who’s gonna be the dissenter and get the finger pointed at them in our Raptors doc?
• Outcome: We know the end of the The Last Dance already, yet it’s still compelling. We know how these Raptors stories end, too, but is it good enough to keep us tuned in?

Let’s get to the eras:

1994-1997: The Isiah Years

Main plot: The creation of the team and commencement of NBA basketball in Toronto. Some scrappy Canadian tech and media moguls scratch and claw and fight to bring an NBA franchise to Toronto, the first one ever outside of the United States. And then it all blows up when the team’s GM — former NBA star Isiah Thomas — tries to take a controlling interest in the team, fails, and walks away from it all. 8/10

Focal point: June 1997 - February 1998. From the draft of a promising high school player, Tracy McGrady, through a lacklustre 1-10 start to the season, up to Isiah’s failed takeover bid and ousting and the trading of Damon Stoudamire. 6/10

“B” plots: Plenty of little side trips to make from this era, including playing basketball in a baseball stadium; the expansion draft; the draft night booing of Stoudamire; the highs and lows of the initial season, including when the Raptors beat the 72-10 Bulls; the firing of Brendan Malone; the perception and reality of players not wanting to come to Toronto (B.J. Armstrong, Kenny Anderson); the risk of taking McGrady out of high school. 7/10

Personalities: Isiah is certainly a huge personality, and maybe we can crack through that smiley veneer and get to see the real guy? Beyond that, we have Damon Stoudamire, who I find fairly interesting; Marcus Camby, who was always outspoken; McGrady, who now looks back at his Raptors days with rose-colored glasses; and vets like Alvin Robertson (certainly a colourful guy) and Tracy Murray. I’m sure it’d be interesting to see what they thought of the city and those early days. Oh, and Oliver Miller! Jimmy King telling Fab Five stories!

Behind the scenes, we have John Bitove and Allan Slaight, as well as Larry Tannenbaum. Unfortunately, David Stern is no longer with us, but league execs like Russ Granik and Rod Thorn can also talk to the process of bringing the NBA to Canada. And I would love to hear what Brendan Malone and Darrell Walker think of those days too. 7/10

Background: We can dig into Isiah’s NBA career and his personality, and the same for key players Stoudamire, McGrady and Camby. We can dig into what it took to get the NBA to Canada, including Toronto’s failed 1987 bid to get a franchise, a story that I don’t believe has ever really been told (apparently, Wilt Chamberlain was involved!); we can also dig into Larry Tannenbaum’s simultaneous 1993 bid, which failed, and how he and MLSE eventually became the owners anyway. We can go back to the Huskies, and I even think we can spend some time on the 1994 world championships, and Dream Team II (ugh), and what that event meant to basketball in Toronto. 7/10

Villains: As in many great stories, Thomas is both the hero and the villain of the piece; he drafts well, says all the right things, but makes some odd moves (like firing Brendan Malone and hiring Darrell Walker) and then sets his own house on fire. Another low-key villain: Kenny Anderson, for refusing to report following the Stoudamire trade. 5/10

Outcome: Thomas leaves, Stoudamire leaves, and the Raptors suffer their worst season in NBA history. But it leads to the drafting of Vince Carter, so it’s not all bad! 6/10

Final score: 46/70

1998-2004: The Carter Years

Main plot: A superstar emerges from a draft night trade and puts the Raptors on the map, giving them their first taste of postseason success... until, once again, it all comes crashing down. 9/10

Focal point: 2000-2001. This will be an interesting doc, because the focal point is the middle of the story. The Last Dance, for example, focuses on 1997-1998, and regularly jumps backwards. Can we focus on 2000-2001, jump backward as needed, but also jump forward in time, to the downfall and end of the Carter era? Might be hard to pull off. But regardless, the 2000-2001 season, with Vince Carter playing at such a high level and then a five-game series against the Knicks and the seven-game series against the 76ers? That’s a great focal point. 9/10

“B” plots: Quite a few, in this era! There’s the Antawn Jamison-Vince Carter draft night trade; the 1998 lockout; the Marcus Camby-Charles Oakley trade; Tracy McGrady leaving; the Marcus Camby-Butch Carter lawsuit; the 2000 dunk contest; the hilariously short Mark Jackson era; the Corliss Williamson-Jerome Williams trade, with JYD driving through the night to make it to Toronto to play the next day. And then there’s post-2001: the Carter injuries, the Chris Childs game, the Nelly concert, Kevin O’Neill, Davis’ comments about the Metric system, the Davis-Jalen Rose trade, phew... and finally the Vince trade. 9/10

Personalities: Well, there’s Carter, obviously, who’s always been a bit bland. But you get to counter that with Charles Oakley! Then you’ve got some beloved Raptors like Morris Peterson, Alvin Williams, Muggsy Bogues and Jerome Williams, and some who’ve had their ups and downs with Toronto fans, like Antonio Davis and Mark Jackson. And if we do take this all the way to 2004, we get Jalen Rose and Chris Bosh too!

Beyond the players, we get Butch Carter, and hoo boy, I bet he’s got some stories to tell. (We can probably get Camby for this too!) I’m not sure what Lenny Wilkens would have to say (he didn’t say much when he was here), but Glen Grunwald can talk to us about the Carter trade and all the various moves he made and didn’t make. And then Kevin O’Neill and Sam Mitchell too! 9/10

Background: Is Vince’s backstory all that interesting? I don’t know. Oakley and Davis have interesting stories, coming from successful teams; Alvin’s story is a good one, coming over unheralded and building himself up into a legit starting guard. Certainly Wilkens has a long history, and we can dig into where Grunwald came from. We might have to mine The Isiah Years for this one. 6/10

Villains: Like with Thomas, Vince is both the hero and the villain of his own story. Would the Raptors have pulled a Grizzlies and moved to the States if Carter doesn’t put his stamp on the franchise from 1999-2001? Maybe! And heck, there’s a whole doc already on what his impact meant to Canada. But to call his exit unceremonious would be generous.

A secondary villain might be Tracy McGrady, who flees town rather than team up with Vince. There’s also O’Neill, who didn’t seem to recognize the offensive potential a team with Carter, Rose and Donyell Marshall had. 7/10

Outcome: We get the high of the team’s first playoff success, and then the first real playoff heartbreak. But we get the slow decline into mediocrity, which isn’t going to leave anyone with a good feeling when it’s over. 6/10

Final score: 55/70

2004-2010: The Bosh Years

Main plot: Bryan Colangelo and Chris Bosh attempt to rebuild the team following the disastrous Vince Carter trade. 5/10

Focal point: 2009-10. The great Hedo Turkoglu experiment, and Bosh’s last season with the franchise, culminating in a disastrous home loss to the Chicago Bulls that knocked the Raptors out of playoff contention with two games to go in the season. 6/10

“B” plots: This one is a bit all over the place: So much happened in those seven years! But how much of it is really that interesting? The Carter trade makes its way in here, right at the beginning. And then we have two very bad years to start, before some real hope creeps in with Bryan Colangelo. It ended so badly, but remember, getting Colangelo here was a coup. BC took over the team and immediately set about reinventing it (even the branding, with the claw logo), trading Rafael Araujo and Charlie Villanueva, and signing Anthony Parker and Jorge Garbajosa, all in an effort to build around Bosh. But then, chasing mistake after mistake: TJ Ford, Jermaine O’Neal, Shawn Marion, Hedo Turkoglu etc. And the drafts: Andrea Bargnani and DeMar DeRozan. The TJ Ford injury — and the TJ Ford vs. Jose Calderon battle. Garbo’s injury. Getting “stuck” with Sam Mitchell after he won Coach of the Year, and then replacing him with Jay Triano. I guess there is some pretty good stuff in there!

We also can’t forget the ‘07 playoff run and facing Carter, the ultimate villain at the time... nor can we forget the hiring of Masai Ujiri as lead scout in 2007. And of course, Hedo’s all-too-real Pizza Pizza commercial... and “ball.” 7/10

Personalities: It’s always fun to see Bosh reminisce about his Raptors time, and maybe this time, we can get him to be brutally honest about it: What was it really like, being part of these teams that were constantly being reinvented? And then the counterpoint of Colangelo, a guy who’s never apologized once in his life, trying to defend all these moves. I think there’s some good drama there.

I’m pretty sure Sam Mitchell would have some things to say about this era too, and I’m curious what Jay Triano thinks of it too.

Let’s also hear Garbajosa’s real feelings about the injury and his return; Ford about his role and injury; Bargnani about the expectations and what he thought his role was; same with Turkoglu. And guys like O’Neal and Marion who were in and out in a season? What did they think of this circus? And what did a rookie DeRozan make of it all? 8/10

Background: Getting Colangelo here, and digging into his background with the Suns, and as an NBA lifer, is a good one. The 2004 draft, too, with Bosh. We can also dive into European and international basketball a bit, with guys like Bargnani, Parker, Garbajosa, Jose Calderon and Carlos Delfino. MItchell’s story, being an NBA journeyman and the Kevin Garnett whisperer, is also solid, and then we can get into Canadian basketball with Jay Triano. Even DeRozan’s background, coming to Toronto from California, makes for a good story, and then there’s Turkoglu, one of the only “name” free agent signings the Raptors ever make (as part of a truly bizarre four team trade), coming over after such a successful stint in Orlando. 5/10

Villains: Colangelo, once again, is both hero and villain; he put things on the right path but then just couldn’t stay on it! Bosh is also a bit of a villain, for his departure, not that anyone could really blame him. There’s Vince, still getting routinely booed throughout this era, never more so than the 2007 playoffs. And then there’s Hedo, who came in out of shape and never seemed interested in either getting in shape, or fitting in with the team. 6/10

Outcome: Colangelo’s moves fail to convince Bosh to stick around, and he leaves in free agency in 2010 and the Raptors end up back at the bottom of the barrel. The postscript: Colangelo sticks around for three more years, trying to build around Bargnani... but at least he makes the Kyle Lowry and Rudy Gay trades right before getting forced out in favour of Ujiri. 6/10

Final score: 43/50

2013-2020: The Lowry Years

Main plot: Under the leadership of Kyle Lowry and Masai Ujiri, the Raptors finally develop the winning culture they’ve been searching for, and it leads them to the NBA title in 2019. 10/10

Focal point: 2018-19. The Championship season. Obviously. 10/10

“B” plots: There’s a consistent build up of success throughout this era, which maybe makes for a little less drama. But, there are still some good stories! We have the Andrea Bargnani trade, the Rudy Gay trade, and the Kyle Lowry non-trade to the Knicks. The “We the North” rebranding, and the Kyle and DeMar friendship. We have the great seven-game series against the Nets, and then the disastrous Wizards sweep the next year, and then, finally ,the Conference Finals breakthrough in 2016. And then, “LeBronto.”

We can dive in to how close Ujiri came to blowing the team up, or at least firing Dwane Casey, in 2015 and 2017. And of course, the summer of 2018, when he did fire Casey and traded DeMar DeRozan for Kawhi Leonard. 8/10

Personalities: Ujiri is always wonderful to listen to, and if we’re doing this doc, say, 10 or 20 years in the future, I suspect there are all kinds of behind-the-secenes stories to be told that Ujiri would never mention now.

Guys like Casey, DeRozan and Lowry will always be connected to this time, and it’ll be fascinating to see what Dwane and DeMar have to say about it in the future. And hearing Kyle and DeMar talk about their friendship never gets old. It’d be great to hear from some of the guys involved in the early part of this run, and get their thoughts on whether or not they saw it ultimately building to a title: John Salmons, Greivis Vasquez, Chuck Hayes, Rudy Gay, Tyler Hansbrough, Landry Fields, as well as some of the era mainstays: Jonas Valanciunas, Patrick Patterson, Delon Wright, Terrence Ross, DeMarre Carroll, Amir Johnson. Always curious to get the perspective of guys who put in the time, and then got shipped out right before the big dance.

Finally, everyone involved in the championship team: Nick Nurse, Serge Ibaka, Marc Gasol, Fred VanVleet and Pascal Siakam, Norman Powell... Danny Green... Kawhi Leonard. Let’s say this is five years after Kawhi’s retired. Maybe he’s more comfortable taking in front of the camera? Could we maybe, finally, truly hear what he really thought of his one year here?

Behind the scenes, we also have two more huge personalities: Tim Leiweke, and Drake. If we can get all these folks on the record and honest, it’s an easy 10/10.

Background: Ujiri, Lowry, Gasol, Ibaka, Siakam and VanVleet all have great stories about how they got where they are and what they had to overcome. I could watch an hourlong episode on each for sure (pretty much already have, thanks Open Gym!). DeRozan’s is solid too, and his early Raptors tenure (“I got us”) is also part of the story. We get to dig into Nick Nurse’s background, coaching in the G-League and in England.

I’d like to learn more about Leiweke, what brought him here, what his grand plan was, why he left so quickly. (I’m sure we can dive into Drake, too, although I’m not sure how interesting that is.) And then there’s Leonard, and his personality, and his story, including the championship with the Spurs and the quad injury and that all going sour. 9/10

Villains: Finally, some external villains! It really can’t be anyone other than LeBron James, the brick wall the Raptors kept running into that they couldn’t knock down or climb over. It was, ultimately, the inability to get past James that prompted Ujiri to finally fire Casey. We also get Paul Pierce in the early days, and the Warriors at the end. 8/10

Outcome: The Raptors win the title, dethroning the dynastic Warriors — following one of the greatest sports moments of all time (you know the one) and digging deep to win four straight against the favoured Milwaukee Bucks. Then the parade! Of course, we also have to talk about Leonard leaving in free agency, but we get the happy postscript of the amazing and unbelievably fun 2019-20 Raptors, and their coronavirus-shortened championship defense. 10/10

Final score: 65/70

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All right, so it’s not really even close: The Raptors 2018-19 Championship season would make the best multi-part documentary series about the Toronto Raptors.

Now, we already have a multi-part documentary series that covers this era: The incredible Open Gym. And if you haven’t watched the past 7.5 years of Open Gym, I mean, what else are you doing right now? Get on it!

But, I’d love a non-team production that truly shows the good and the bad — something not even The Last Dance, sanitized as it is by “Team Jordan,” has been able to give us. If, 20 years from now, we’re all watching a 10-hour series called “The North Rises” — and hopefully not during another pandemic! — I will be a very happy Raptors fan.