An Ode to a Giant of Africa: Masai Ujiri & his legacy with the Toronto Raptors
To quote Masai Ujiri: Today is not a good day.
Being black in Canada is not easy. It is a challenge I can't speak on due to it not being something I can experience, but it is one I am aware of the historic racism that stems from the deep colonialist roots that Canada has spawned from, how it informs the statistics & experience Black Canadians go through across the country. How systemic racism plays a role in black Canadians having to work harder compared to their non-Black counterparts and how much harsher their work is critiqued in that same comparison. Segregation in the Maritime provinces, one of the many blemishes on Canada’s historic mistreatment of visible minorities. Racial profiling & statistically harsher sentences for the same crimes, to say nothing of serious issues like carding which disproportionality affect Canada’s black community or anti-black racism permeating Canada’s healthcare.
The injustice stands in contrast to the “Fair & Just Society” Pierre Elliott once espoused. Anti-black racism affects all walks of life for Black Canadians, no matter the wealth one may have at their disposal under capitalism.
Case in point: You can work your way up from scout to the most successful Toronto sports executive of the 21st century & fired by a man with a fraction of the capabilities and incomparably less visionary, someone who never once had to work a day in his privileged life solely due to his family’s name & the ground laid by those who came before him.
You can deliver a championship to one Rogers-owned team & only hold your job for 4 more years than another whose leadership has mired in mediocrity despite the talent the Blue Jays have had under Ross Atkins, the latter of whom is still employed while the Jays are in a perpetual purgatory of chasing a wildcard spot. The former of the two? Slandered as “not worth it” by a maple MAGA owner when exceeding Ross’s performance in all metrics one measures success.
You can have more years of success than failure but somehow have those failures drown out the discourse despite the glimmer of the Larry O’Brien & 50+ wins you ushered in with the talent you accumulated, to say nothing of how inflated the failures are compared to your success or how many franchises would kill to be on that same level.
You can have your legacy questioned, derided the very day you’re let go despite the demonstrable impact you had on the organization from top to bottom by spineless businessmen lacking your vision for a winning team or your passion for a sport that the entire nation loves even if its feelings for the city of Toronto are far more complex.
This is the story of Masai Ujiri, the Toronto Raptors most recent Vice President and the man responsible for Canada’s greatest sports success outside of the Winter Olympics. His tenure had its share of mishaps but it was transformative all the same. It turned an expansion franchise of chortle-worthy renown into one of the most respected in the league.
But let’s not jump too far ahead just yet. Let’s go back to prehistoric times!
B.C. - Before Competence
Before we get into Masai Ujiri's historic turnaround, it's important to give some context for the Raptors before he came through the doors for the younger fans - or even older fans who’ve forgotten the dark days after Masai Ujiri ushered in the most successful era of the Toronto Raptors in their history. 13 years of the franchise’s 30 years of existence is a long time, after all.
During the years before Masai, the Toronto Raptors management were, in a word, an embarrassment. Despite having some notable names drafted to them in the 90s like future Defensive Player of the Year Marcus Camby, future All-NBA Vince Carter and future Most Improved Player & “reason the Magic weren’t a complete joke in the 00s” Tracy McGrady, the teams around these players were lacking in worthy supporting casts, not helped by management’s ability to retain what talent they acquired via the draft was inept.
Stars didn’t want to stay there, players who would become impactful wouldn’t stick around to develop into them and the teams trotted out were never able to support the draft success stories they had. It didn’t help that, while one can point to a handful of decent trades like moving the pick that became Johnathan Bender for 2002’s savior Antonio Davis, most of their moves either immediately blew up in their face or the bomb would go off in future years like the prospect moved for Jermaine O’Neal becoming All-Defensive 2nd Team Roy Hibbert.
You can trace a lot of this instability regarding stars not wanting to stick with the Raptors back to the precedent Damon Stoudamire set when he infamously called out then-GM Glen Grunwald after a failed trade to the Rockets. But if Stoudamire started this sentiment, Vince cemented it with an exit that no superstar has ever come close to, with both player and organization exuding a toxic level of vitriol at one another including a now infamous revoking of a parking spot that once belonged to Vince’s mom. At the end of the day, Vince got his way and the franchise got pennies on the dollar for someone who once could have commanded Dirk Nowitzki and Canada’s own Steve Nash - the latter being a player the Raptors would go on to fail signing in free agency way down the line.
The less said about how the franchise squandered the few assets they got from moving the then-most important player in franchise history, the better. With such instability & incompetency, it’s no surprise that the franchise’s high up to 2013 was winning 47 games and a 7-game slugfest with the 76ers in the 2nd round - and even than series has its share of controversy surrounding it. From the early days Isaiah Thomas to the final days of Bryan Colangelo, fans had little to hang their caps on.
A few divisional champion banners in a league where divisional rivalries are of little consequence & even less intensity.
A whopping four seasons where the team broke over 0.500 (They were an even 41-41 in 2007/08).
A Dunk Contest.
What few moments of triumph Toronto could claim from the 90s to the early 00s like a late turnaround for their 2001-02 season sans-superstar Vince Carter was marred by the reality that they failed to make much of any noise in the postseason. The front office couldn’t construct a roster worthy of the talent they managed to acquire in the draft - at least when they were able to hit on players in the draft.
The Bosh era in particular is bleak. A single winning season. 3 playoff wins across 2 berths. Chris being a perennial All-Star and resembling the mascot more than any player in franchise history. While there’s some intrigue to be had over what could have been if the team drafted better during the Chris Bosh era, the reality is the team during CB4’s time with the team was marked by one mistake after another.
Choosing Andrea Bargnani over LaMarcus Aldridge in 2006 (Picked right after him)? going with Rafael Arujao over Andre Iguodala (Picked right after him)? Selecting Joey Graham over Danny Granger (Picked right aft- noticing a pattern)? The Jermaine O’Neal trade? Not confidence inspiring for any salvaging this particular time for the franchise.
So grand are the franchise’s early woes, so stark in contrast are the names on the court with the clownishness of those off it that one can’t help but look back at the old days wondering how things might have played out with a different captain at the helm. Frankly, we’ll never know what that young Raptors core of Vince, Camby, Stoudamire and McGrady could have been if they were able to keep the team together; Tracy was infamously inefficient before he broke out in Orlando so who knows if he ever becomes the Hall of Famer we know him to be today. Ditto Marcus Camby who had his noted bouts with then-Coach Carter.
Yet, one can’t help but let the mind wander & be optimistic that talent would triumph over any adversity a young expansion team may have faced along the way. Tracy McGrady himself has stated that the Raptors with him and cousin Vince could have made the Finals, even expressing regret over leaving. That regret isn’t an uncommon sentiment amongst the early Raptors legends, as both him and Damon have said something to the effect that they would have stayed had the same leadership & organization existed back in the day - that they would have won if they kept it all together.
Let’s meet the man who made like Optimus Prime & transformed Toronto’s image across the league.
The Masai-ah
On May 31st, 2013, the Raptors made what would become the most consequential signing in franchise history when they landed a man by the name of Masai Ujiri as their new General Manager/Vice President of Basketball Operations. The scout-turned executive was not new to the NBA’s managerial side, having successfully navigated a paradigm shift in trading away a franchise star in 2010 & coming off a freshly constructed 57 win roster that led him to winning him Executive of the Year. The team he’d join had already done the former, having moved Bosh in a sign and trade to Miami that returned their own first round pick and a future first.
It may seem in retrospect bizarre for Masai to have left for a Raptors team that won 34 games the season prior but there was a kernel of history between the two; Ujiri’s aforementioned scouting background included being the Raptors Director of Global Scouting & Assistant General Manager to Bryan Colangelo in 2008. Coincidentally, 2008 onward was when the Raptors drafting success in the Bosh era managed to turn around as they selected two future All-Stars Roy Hibbert 17th and DeMar DeRozan 9th during Ujiri’s decidedly shorter tenure with the team.
However, DeMar wasn’t an All-Star when Masai had joined & the roster he inherited decidedly less talented than the one he left behind. His first major move? Sending away the former #1 overall pick Andrea Bargnani to the New York Knicks in a move that yielded, among the players that came back to Toronto, a first-round pick. An unfathomable thought given Bargnani’s reputation as the stereotypical soft European with lowlights aplenty & rebounds so few.
Though it wasn’t the move that turned the franchise around, it was a sign of things to come. Out was the aimlessness of Colangelo’s building during and post-Bosh, in was surgical precision & a stern evaluation of the talent of the previous regime. No one was sacred & not one player on the roster was above being traded. Kyle Lowry, so shortly after being given a stern talking to by Masai about what was & wasn’t under his control, was nearly dealt to the Knicks in a deal that was nixed at the final moment.
But while that move falling through wasn’t under Masai’s control, at least not directly as the veto by Knicks owner James Dolan was in part due to James’s disdain for the Bargnani trade, there was one move where Ujiri was in full control of & its impact is still felt to this very day.
On December 9th, 2013, the team’s leading scorer Rudy Gay was sent to the Sacramento Kings for a handful of players, most notable among them being Greivis Vásquez. The Gay trade marked a turning point for the franchise’s fortunes and the Vásquez trade tree is still yielding dividends to this day as the pick he would eventually be traded for would become O.G. Anunoby who in turn was turned into two current starters in R.J. Barrett and Immanuel Quickley, not to mention bench big man Johnathan Mogbo.
Such was the brilliance of Masai in the 2010s. Always meticulous with setting the team up for success in the moment, always making moves to fuel future success. The Raptors of 2013/14 would see their first All-Star since Bosh had left them & more importantly, a record of 48 wins - the most the franchise had ever seen.
The playoff series that spawned from this was memorable. More than the dynamics of old stars vs. a young hungry 3 seed, more than the continued animosity of the Nets & Raptors rivalry than first began with Vince’s infamous trade to them in 2004, it was an outburst by Masai before the bloodbath began that endeared him to the public.
On April 19th, 2014, the general manager of the Toronto Raptors uttered two words: Fuck Brooklyn. In the moment, it felt like the top brass & fans were on the same page. Both passionate about this team. Both committed to winning. Though the Raptors would lose in 7, this bout would come down to the final possession with Paul Pierce blocking Kyle Lowry’s game winning attempt.
Clearly, there was still work to be done beyond hoping for improvements from the young DeMar & an emerging Kyle - the latter of whom was extended for 4 years after the thought of sticking around in Toronto previously prompted Lowry to say “You can kiss my ass”.
Stay Winning
The 2014 season was the beginning of a new identity for the team. The “We the North” era was defined by its All-Star duo of Kyle Lowry and DeMar DeRozan on the court but off the court, it was most notable for the careful crafting by one Masai Ujiri.
Masai had a dream: Win a championship in Toronto. He had a vision he’d share with fans & he had the charisma to sell even the most jaded amongst them on his plan. His actions matched his ambitions. Never idle, he would tweak the roster with meticulous consideration and with sublime results throughout the mid and late 2010s.
Though not all of these moves were successful in trade or draft - Bruno Caboclo anyone? - the success stories far outweighed anything one could consider a blemish when the results were multiple 50 win seasons and frequently topping the previously held record of most regular season wins. We don’t have the time to go over every single one but here’s but a few of the more notable moves made during the most winningest era of Raptors basketball:
Even though it became something of a commonality for Masai, finding value in late first-round is rarely easy. The Raptors did just that when they picked arguably the best player left on the board in Delon Wright 20th overall during the 2015 NBA Draft. A 6’5 guard who would be a key contributor for The Bench Mob in years to come & one of the many solid additions that made future Raptors teams so deep with the different options at coach Casey - later Nick Nurse’s - disposal.
Speaking of the 2015 draft, the aforementioned Vásquez trade tree would sprout its first branches when he was traded & the first of the two draft picks selected with it - Norm Powell in 2015 - made a pivotal play with a steal & slam dunk to tie a nailbiter of a series against the Paul George-led Pacers in the playoffs. There’s an argument to be made that Powell’s dunk saved this era of Raptors basketball, preventing it from going down a very different path & he’d play a critical role in the years to come.
He managed to get MLSE to invest $30 million in the construction of a practice facility around the same time the NBA awarded Toronto the honor of hosting its first ever All-Star game in the city, an investment in the franchise’s long-term future & one lauded by the players after being previously subjected to a miniscule training room.
Internally, he elevated women in MLSE, promoting an equitable & diverse organization that reflected the city whose slogan is “Diversity Our Strength”
The 2016 NBA Draft is the best the Raptors have ever had, bar none. 2 All-Stars (Albeit one of whom was technically an undrafted free agent), one of whom being 2x All-NBA in Pascal Siakam & current starting center Jakob Poeltl who himself was in the trade that famously brought Spurs superstar Kawhi Leonard. Did I mention the pick that became Jakob Poeltl was from the Bargnani trade?
Moving a bottom-5 first round pick & one fan-favorite in Terrence Ross to acquire new fan-favorite Serge Ibaka during that 2016/17 season added a tenacious defender in the backcourt that further fleshed out the Raptors depth and added something of an enforcer to the team that they lacked.
The Raptors squads he assembled were winners. Increasingly deep and never lower than the 4 seed, they made their first ever Conference Finals 15 years after Vince’s failed buzzer beater. Though they lost in 6 games, they did so to the eventual champions so there was reason to be patient with this team. To build further on a seemingly steady foundation.
But at some point, it became clear that changes needed to be made. 2017 & 2018 both spawned 50+ win with 2018 standing as the franchise’s best regular season outing at 59 but both resulted in a sweep against the LeBron-led Cavs. As long as LeBron was in the East, Toronto’s status as a contender would always be in question no matter how many wins they had in the regular.
That changed in 2018 when LeBron moved conferences to join the Lakers and the East? It was ripe for the taking.
It was also time to make a very difficult, very painful decision to take the Eastern Conference. Because with or with LeBron, changes needed to be made.
Dynasty Slayer
2018/19 is a season that speaks for itself. It almost feels disrespectful to say that but let’s be frank: You watched it, I watched it. From East coast to West, sports fans saw their team, the Toronto Raptors, win it all in one of the most memorable Finals run of the past 20 years, with one of the deepest teams to ever go all the way.
Masai was the architect of that Mariana Trench team, up to and including making the late season acquisition of Marc Gasol. The team’s success was the culmination of Ujiri tirelessly toiling & tinkering with the roster, adding just the right pieces for a superstar when the moment came for it if they didn’t find someone to develop into one. His seasoned eye for scouting gave them a solid supporting cast & the pieces to eventually make an all-in push that yielded Kawhi Leonard doing his best Michael Jordan impression, giving up DeMar DeRozan and Jakob Poeltl in the deal that few fail to recap also saw Danny Green come to the Raptors. It’s doubtful a lesser exec would have given up as little as they did and even more doubtful Toronto would win it all if Masai hadn’t correctly evaluated Gasol as that final piece.
A less decisive leader likely would lack the fortitude to so quickly cut the most winningest coach in Raptors history Dwane Casey so soon after he won Coach of the Year nor promote internally the perfect madman of a rookie coach to head a contender.
Moreover, it’s doubtful a lesser executive would dare trade away the face of the franchise in DeMar DeRozan for a player like Kawhi who was not only seen as a rental but actively did not want to be in Toronto. It’s easy to say the results speak for themselves when we have the benefit of hindsight but this move? At the time, it was a a calculated risk that could have gone horribly wrong if a lesser manager or president fumbled the opportunity such a talent presented to a team.
Masai was of course no lesser executive & while Jon Horst won Executive of the Year, Ujiri’s Raptors beat Horst’s Bucks in 6 in their 2nd Conference Finals appearance before taking home the O’Brien & ending the Kevin Durant Warriors era. A win is a win, but the decision that preceding said win was not an easy one for him to make.
A Moment Ruined, A Half-Decade in the Wilderness
Context matters. It paints a full picture of a period in time. It helps to inform one’s interpretations of future events.
In this case, the context to view much of the post-championship/pre-Scottie Barnes era comes from a moment that ruined what should have been Masai Ujiri’s greatest moment.
On June 13, 2019, the night the Toronto Raptors won 114-110 to reach basketball’s El Dorado, Masai Ujiri was assaulted by a police officer when Ujiri tried to cross the floor to celebrate with the team he meticulously created, supposedly for “lacking the credentials”.
Said pig’s department would later lie about Ujiri striking them in the jaw - even threatening charges of battery - before body cam footage would detail the incident & make it abundantly clear that, indeed, the county’s cops were lying through their teeth.
This incident robbed Ujiri of what should have been his highest high, transforming this moment of triumph, the payoff to the years he devoted to running the Raptors into a painful reminder of the system racism that black people face from law enforcement across North America.
Masai has spoken about how he wasn’t able to enjoy the championship because of this moment along with the swift need to negotiate with Kawhi so what’s the best way to rectify that? Win another championship, of course!
Problem is, winning a championship is hard. As we saw this very year, even a historic season like the 68-win OKC Thunder is no guarantee of one being able to lift the Larry O'Brien trophy. It’s that adversity which makes winning at the highest level all the sweeter, the narrative all the richer. It’s why the 2019 Raptors are as beloved as they are by fans of all walks of life. Coming back down 0-2 to beat the Bucks in 6? A grinded out 7 game series where it comes down to the most iconic game winner since Jordan’s final shot as a Chicago Bull? Duking it out with the dynasty of this generation of basketball? It’s a compelling story from start to finish of an underdog that came out on top.
It was also a story that would be hard to write a direct sequel to. However much one wants to debate Kawhi Leonard leaving was inevitable or not, whether the Raptors were or weren’t serious about that proposed Westbrook/Paul George trade or being used as leverage against the team that Kawhi ultimately signed with, the fact remains that replacing superstar production when it’s lost, either internally or externally, is extraordinarily difficult. The 2019/20 Raptors still had depth, Siakam continued to rise as one of the NBA’s newest stars alongside fellow 2020 All-Star Kyle Lowry but beyond the age of their supporting cast and declining production, a literal pandemic postponed the season and upended the entire NBA.
And yet…they won 53 games. They were on pace for 60 games before the pandemic interrupted event after event across the globe & shortened the season after resuming it in The Bubble. Perhaps they’d mount a more tenacious title defense had a literal global pandemic not derailed Pascal’s first All-Star season’s routine to the point where he hadn’t touched a basketball in some time.
The core was aging but still competitive with some of the best teams in the East, something on full display with the Raptors dragging the Celtics to a pivotal Game 7 in the Bubble in spite of a poor showing from Spicy P. They were competitive and more importantly, they had continuity from their championship core.
And therein lies the conundrum of this particular era. They were closer to being a contender than they weren’t and thus trying to justify the chase for that elusive 2nd championship with the current core that came up short instead of tearing it down & rebuilding after they lost Kawhi.
Every basketball executive wants to be the next Spurs. They want to be this pristine, everlasting dynasty that seamlessly transitions from one superstar, one era to the next. Endlessly in contention, avoiding the dreaded grasp of the rebuild ghost that awaits almost all sports franchises. Problem is, building a dynasty the Spurs saw requires the sort of generational luck San Antonio has to go from David Robinson and Tim Duncan to the Spurs Big 3 to Kawhi Leonard with 5 rings from beginning to end. In other words, you need one of the greatest players of all time to be your tether. No one on this Raptors team came close.
Masai’s courting of Giannis Antetokounmpo in 2020 was well noted for actions both subtle and overt - it’s frequently pointed out how Fred VanVleet’s contract was structured in such a way to free up as much cap space as possible to sign the Greek Freak and one of Ujiri’s first moves is a now infamous attempt to trade back into the 2013 Draft to acquire Giannis - he could have been the player to bridge the gap from Kawhi to their new bright star. But that’s not how history played out.
More importantly for this story, having the sort of endless winning San Antonio saw from 1999 up until Kawhi’s final full season with the Spurs in 2017 brings with it job security. It’s hard to fire anyone who’s doing their job well & no one would dare deny Masai was one of the top executives in the league in 2021.
No one but Dishonest Ed, that is.
An Aside to the Asinine & Capitalism
Edward Rogers, Canada’s least loved telecom nepobaby & noted friend of fascist Donald Trump - a person who Masai Ujiri rather famously critiqued the then-president of the United States for racist remarks Trump had made about African countries being "shitholes" - was a minor figure in the story of Masai & the Raptors until 2021 where it emerged that Ed didn’t want to pay Masai Ujiri the $15 million dollars he would eventually be re-signed for.
$15 million sounds like a lot of money because it is…if you aren’t one of the most notoriously profitable, deservedly hated telecommunication companies in all of Canada & in ownership of one of the most valuable franchises in the NBA - one whose valuation had ballooned into 2.5 billion at the time this standoff became public knowledge (Now $4.4 billion, for the record).
But somehow, $15 million? That’s too much.
For those outside of Canada, it cannot be overstated how inescapable Rogers is as a company or how thoroughly despised the brand is between their atrocious customer service, price gouging, hidden fees & false advertisements, not helped by the family behind the company. They’re the equivalent of Comcast only arguably more evil & with Canada’s telecom trio of Bell, Rogers & Telus forming an oligopoly of heinous proportions. Relative to other countries, Canadians pay more for less in data for their phone plans, internet speed & in general have less alternatives to avoid the terrible trio than the likes of Australia, India, Finland and several other countries.
Rogers in particular somehow manages to be the worst of the three while simultaneously the most thoroughly entrenched in more day-to-day matters than your average Canadian may be aware of. Building a toxic work culture that encourages employees to lie to customers in order to meet sales quotas comes to mind, as does the infamous service outage that left 12 million people unable to withdraw money from the bank or pay for their most basic needs. But we’re not here to talk about why we need stronger anti-trust laws to break these three up or that we should be nationalizing Canada’s telecommunication infrastructure…even if we should be doing that.
Let’s get back to the dynastic family behind the infamous Rogers name. Part of how Ed rose up as the head of his father’s company was through what can only be described as a corporate coup. Constant interference in the work of then-CEO Joe Natale while Ed misled his own mother by providing her with false information about Joe not meeting targets to oust Joe in favor of Ed ally & butt dialer Tony Staffieri as Ed installed board members loyal to Ted Rogers’ deservedly unloved son to secure control as chairman of his father’s company and in control of his family’s trust.
If that sounds familiar - interfering in operations, attempting to assert more control & a focus on profit above all else in a time where amenities have become less affordable than ever - you’re not alone. For some time, Ed Rogers was reportedly trying to sabotage Masai Ujiri in a manner that drew comparisons to the then-ongoing struggle for control of the Rogers company at the time when initially reported:
New details have emerged suggesting that behind the scenes Edward Rogers tried to sabotage a high-performing executive with whom he had grown disenchanted — & ultimately failed in his bid because he appeared not to fully understand the governance structure of the NBA franchise.
…
The sources said some time after the meeting, Rogers called Ujiri & told him he wasn’t worth the money he was being paid. The NBA source said the call left Ujiri feeling so angry & disrespected by Rogers that he considered taking a year off as president of the Raptors.
A quick aside to this already lengthy tangent: At the time of this purported sabotage, MLSE - the organization that controls, among other teams, the Toronto Raptors - was owned by three companies, those being Rogers, Bell & Kilmer Group, the latter being owned by then-governor for MLSE Lawrence “Larry” Tanenbaum. That is no longer the case as Bell have sold their stake in the company (Giving Rogers & thus Ed 100% control with a 75% share in the company) & Tanenbaum - who ultimately overrode Ed’s brazen & bizarre - sold off a small portion of his own stake to OMERS to help start up the WNBA team that Ed Rogers was also opposed to.
Still, Tanenbaum was able to override Eddie’s nonsensical requests & provided Masai Ujiri the contract he deserved despite Ed’s sound of fury failing to get the NBA to intervene. Ujiri was only two years removed from a championship and the pandemic had a dramatic effect on team operations across the NBA. The Raptors were uniquely affected by the pandemic with how they were stranded from their home given they were playing at away from home even when at home every night in front of fans who were at best ambivalent to the team and at worst, more excited to cheer for roleplayers on the opposing team rather than their stars. Being exiled to Florida & the indignant “fans” of Tampa Bay who’d flatout boo the team in their home stadium makes it easy to overlook them missing the playoffs for the first time in almost a decade, even if didn’t make the season overall any easier to stomach.
Toronto is My Home
You know what makes it even easier to get everyone to forget your first failure to make the postseason since becoming head of the team? Making it back to Canada & the playoffs with a shiny new Rookie of the Year.
2021 was a miserable season but it had a bright spot between Aron Baynes various lowlights in the Raptors having the 7th best odds in the lottery: Those odds and a dash of luck propelled them to jump up to 4th overall. Masai’s eye for scouting shined once more as he went against consensus to select Scottie Barnes over Jalen Suggs, a decision that made an immediate impact when Scottie dropped a 25 point double-double in a win against the Boston Celtics.
Scottie would of course go on to win Rookie of the Year, only the 3rd Raptor to ever do so & the first since Vince Carter. Unlike those two, this selection saw Scottie & the team make the postseason as the 6th seed though Barnes missed much of the playoffs due to an injury caused by Joel Embiid. The Raptors lost in 6 games but 48 wins and making the postseason counts as success.
And yet, buried in that year lay a seed that would grow into a troublesome weed that the franchise failed to uproot: The Thad Young trade, itself the result of the Kyle Lowry sign and trade which brought back a very grump dragon in one Goran Dragic.
Remember when I said every team wants to be the Spurs? Well in the same way that the two threepeats of Jordan’s Bulls papers over the mess they were behind the scenes, so to were the wins of San Antonio in spite of plenty of mistakes & messes that San Antonio needed to clean up. Granted, said mistakes weren’t generally on the level as “a teammate has an affair with another teammate’s spouse” but they were made, buried underneath the sea of success of 5 championships and several more Finals trips over literal decades.
No dynasty is without its share of skeletons or missteps. What distinguishes them from other team is how management manages to navigate the seas when they become particularly choppy. What separates the 2010s and 2020s for the Raptors thus far is one managed to bandage its minor while the latter would go through small slit after small slit to limb after limb.
Drafting Bruno Caboclo was a proverbial gamble that didn’t pay out but it didn’t cause the franchise to go bankrupt since they had a solid foundation of reliable roleplayers and two promising stars in DeMar DeRozan and Kyle Lowry in 2014. They managed to bounce back in 2015 with one of the many marginal hits in the late draft by selecting Delon Wright before going a solid 3/3 in 2016 with Pascal Siakam and Jakob Poeltl along with undrafted free agent Fred VanVleet. That’s a good organization making smart decisions after a minor setback.
Yes, the DeMarre Carroll signing was bad & it very well may have cost the Raptors the chance to get Shai Gilgeous-Alexander due to being out of the 2018 Draft. It didn’t crush the franchise because the team in 2017/2018 was incredibly deep & once more reaped the rewards of the past; Greivis Vásquez yearly dividends came in the recently drafted O.G. Anunoby who was good enough that coach Casey felt confident enough to have him guard LeBron James. Same verse, same as the first: Good management led by Masai righted the ship and kept them on course.
Like the Spurs going from one long postseason run to the next, Masai at his apex would rebound from a minor mishap with aplomb. In contrast to the 2010s…well there wasn’t any one move one can point to as that during the 2020s. Drafting Scottie Barnes was franchise-altering in many ways & it would be uncharitable & untruthful to paint the 20s as one failure after another.
Similarly, focusing too much on the missteps of Masai &the Raptors during this time risks exaggerating the failures of Ujiri’s late tenure. However, it is undeniable that mistakes were made & at the heart of it was clinging to that desire for a 2nd championship based on the performance of a team that wildly overachieved in 2022
Once again we won’t go over all the mistakes so consider the following a short sample:
Toronto wasn’t the only team to miss out on Desmond Bane in the 1st round and the 2020 NBA Draft is rather infamous due to how scouting was affected that year by CO-VID 19 i.e. the cancellation of March Madness but they were the team that selected Malachi Flynn one spot before Bane would go one to be a key contributor to the Grizzlies up and down but nevertheless rising from the Grit N’ Grind ashes rebuild before being moved in a haul to the Orlando Magic. Flynn, on the other hand, is on the outside of the league looking in after his rookie contract came to a close.
Losing Marc Gasol & Serge Ibaka in a vacuum may not have seemed like it as big of a talent drain as it was due to declined played & both having two of their worst seasons with the Lakers & Clippers respectively, but replacing their play in the paint with center Aron Baynes would be seen as even more disastrous were it not for that lottery luck that brought Scottie Barnes to Toronto.
The other center of this Siakam-led era, Khem Birch, had his moments during Tampa Bay but injuries & an overpay hampered one of Canada’s own & the team’s bench production as a whole.
Moving Norman Powell for Gary Trent Jr. wasn’t initially seen as a mistake; Trent’s 30 bombs & propensity for successful gambling on steals made it seem like the Raptors swindled the Blazers during that bounceback in 2021/22. In the long run, Trent Jr. failed to make the improvements expected of him, never really living up to the contract given to him (the one which had the exact same dollar amount as Powell got paid, minus the years Norm had on his own). Put another way, Norm exceeded his contract that he’s still under - now with the Clippers - while Gary was on a minimum with the Bucks last year to recoup his value in free agency.
That aforementioned weed seed of trading away the team’s 2022 first-round pick to get rid of the moody Goran Dragic in favor of a player the Spurs planned to waive in Thad Young effectively moved the team out of drafting Andrew Nembhard and Walker Kessler - either one of whom offered the Raptors something the team was in dire need of and one of which the team was reportedly interested in.
In general, the Kyle Lowry sign and trade was a miss - the aforementioned Dragic cost them draft capital to dump instead of bringing some in and it’s an open question if the other piece of the Lowry return in Precious Achiuwa will be in the league next season - but it was a miss that a franchise who traded its franchise leader in points & presumed Raptors lifer had to take to salvage some goodwill despite it ultimately being the right call in 2018.
The Jakob Poeltl trade in a vacuum seems like good value, a first-rounder and a pair of seconds for a starting-caliber center is a bargain in today’s market where injury-prone Mark Williams commanded two firsts, but when a team out of the playoff picture (At the time the Raptors were 7th in odds for the 2023 NBA Lottery) trades away its own future first with lightly protections, it can’t come as a surprise when that move came back to bite the team or their eventual rebuild when they were without the pick that would become Rob Dillingham in 2024, owed to some bad luck in that year’s lottery.
On a similar note, signing Otto Porter Jr. seemed good on paper for a team in need of shooting but Porter’s inability to stay healthy during his short stint with the team relegated him to being a footnote in the Pascal Siakam trade.
Speaking of Pascal, while Masai and Bobby ultimately did a good job managing the few assets they got out of the deal, effectively turning him and a future second into Ochai Agbaji, promising rookie Ja’Kobe Walter and an All-Star-caliber wing in Brandon Ingram, one can’t help but imagine the assets they’d have to work with would have been greater had they been more forward with extending Pascal for what he’s worth rather than dangling him as an expiring when the 2x All-Star’s agent had the ability to dissuade any suitors from giving up a haul by saying his client preferred to stay in Toronto.
Losing Fred VanVleet can be spun however one wants but at the end of the day, there was a deal on the table for a future first & players they could have rerouted for future assets or potentially kept as depth pieces, possibly as veteran voices in the locker room for a new young core, which is more than what they got when Fred walked. If Masai and company were more decisive at the 2023 NBA trade deadline, it’s doubtless that their rebuild would be much further ahead than it is at the end of the 2024/25 season - and there is something to be pondered about whether having Fred as a Buck would have changed where Damian Lillard landed the offseason he requested a trade if Milwaukee lacked that pick.
Some of these moves being so consequential was wholly unforeseen - no one expected Fred to sign with the Rockets for $128 million in the offseason nor 2022 rookie Christian Koloko to develop blood clots & if he managed to cut it as a reliable backup big or even showcase starter-level material, perhaps the Thad Young trade would have left a less bitter taste. Some of them look worse due to the benefit of hindsight like moving Norm Powell for Gary Trent Jr. Some of them were bad due to context like the Jakob Poeltl trade, most especially at the time because of Toronto losing games to the guy they effectively traded out of in the Jazz’s center rookie Walker Kessler.
Some of them weren’t in the team’s control; scouting for the 2020 NBA Draft’s prospects was an endeavor for even teams acclaimed for finding talent so late in the draft due to the pandemic transforming more than just sports, even if Masai missed in a range he previously excelled in drafting roleplayers and All-Stars alike.
What they all share in common is that they were minor. They were not overtly consequential when viewed individually or in a vacuum. But much like a chequing account with some single digit monthly fee, they add up over time, leaving the team in purgatory, the players in a state of discontent and the team lacking major assets to move around.
Missing on one draft pick is manageable. Losing one or two rotation players - even with the benefit of hindsight with how Ibaka and Gasol fell off a cliff after leaving the Raptors - can be managed if there’s someone who can step up to replace them or a trade to fill in that void. But having one mistake after another left the team adrift at sea and at risk of drowning when its biggest success story pre-Scottie was G-League MVP Chris Boucher becoming good enough to crack the rotation yet inconsistent enough that he was never seen as the second coming of The Bench Mob™.
It would be one thing to lose Fred VanVleet for nothing in the 2023 offseason entering the 2023/24 season. But not owning your 2024 1st when said pick was sent out with light protections in a shortsighted attempt to chase a playoff seed, a notoriously lengthy coaching search and two key pending free agents trying to play for their next big contract concocted a season most foul for a rebuild that felt impossible to avoid and yet one where the team couldn’t even reap the benefits of its own failures via a high lottery pick as the results of previous mistakes to build on a new young core.
We can argue all day about if or when the team should have blown it up, if they should have traded for Kevin Durant back in 2022 or whichever offseason one wants to mark as the inflection point. The fact of the matter remains that retaining continuity of the 2019 Raptors failed to translate into replicating any sort of success and the decisiveness of old was replaced with far more patience than the current core perhaps deserved.
Still, if Toronto was to rebuild, it had a young cornerstone in Scottie Barnes whose All-Star appearance was one of the few bright spots of that 2023/24 season. And in all likelihood, it still had the right man for the job - even if recent years may have shaken some confidence in the fanbase’s collective consciousness.
Legends Never Die
In 2023, the Denver Nuggets made their first ever Finals, winning a title for the city of Denver in 5 games against the Miami Heat. It was a moment of triumph after several years of bad luck and worse health.
One of the people that had an indirect hand in that championship? 2013 Executive of the Year Masai Ujiri.
Like the Bargnani trade that came after it, Masai made a habit of fleecing the Knicks when he traded pending free agent Carmelo Anthony to New York in 2011 for, among other pieces and players in that haul, the pick which became the Robin to Nikola Jokić’s Batman in Canadian guard Jamal Murray. Granted, Masai didn’t make that pick as he was long gone by the time it conveyed.
I don’t want to do a disservice to those that came after Masai in Denver - it took some serious gall for Tim Connelly to decide that the 41st pick would be the Nuggets cornerstone over the more coveted Jusuf Nurkić, especially when the post-Masai Nuggets were struggling in an ultra competitive Western Conference. Moreover, the 2013 squad he put together that won 57 games was unrecognizable to the one a decade later that won less games but went all the way.
That being said, it goes to show the impact that one timely move can have on a franchise in the long run, even if you’re not around to see the house project that began with previous management come to fruition under your watch. Without the pick that became Jamal Murray, Denver probably have a much harder path to a title run than they do in 2023 if any of the years between Bubble Murray & his return from an ACL tear are anything to go by. Indirect or not, Masai Ujiri made his mark on the Nuggets - albeit not the same one he did with the Raptors.
Masai’s firing - and let’s be blunt about it, Ed Rogers through invertebrate mouthpiece Keith Pelley fired Masai Ujiri - came off the heels of the NBA Draft, of which Ujiri was present & involved in the decision-making. His last mark left on the franchise is the pair of picks made at 9th and 39th with Collin Murray-Boyles and Alijah Martin respectively.
There’s been some recent contention about the selection of Collin owed to a report that Masai was interested in Khaman Malauch but however one wants to interpret that tidbit or weigh it against a selection for a player whose profile matches the lengthy, defense-first players Masai has been known for, the fact remains he’s left the franchise in the midst of a rebuild with some interesting young pieces in an Eastern Conference that remains wide open for this Raptors team to make an unexpected playoff push much like the unforeseen march to a Top 3 seed in the East that kicked off Masai’s time in Toronto.
Ujiri said Toronto will win another championship and if they do so in the next decade, we’ll be quick to look back at the moves that paved the way for the Raptors next ring - but we won’t have to look very far to see the legacy Masai has left for himself nor any of the pieces that may play a part in that story. Ja’Kobe Walter showed a lot of promise as a rookie and Gradey Dick’s sophomore season started out with him looking like a borderline All-Star far ahead of schedule. Let’s also not ignore the sorcery that he managed to unleash in somehow eking out assets from one of the worst Raptors to ever don the dinosaur in Jalen McDaniels via Jamal Shead and the recently drafted Alijah Martin via an early 2nd round pick. That plus a Lakers 2nd in 2026 is nothing to sneeze at.
If the Raptors are competitive next season, we can all point to the savvy drafting and meaningful moves on the marginal Masai built a name off of as a huge reason why, up to and including pulling Brandon Ingram out of the bargain bin known as the New Orleans Pelicans.
Masai Ujiri’s impact goes beyond Toronto. Beyond Canada. Beyond borders. His work with Basketball Without Borders has been profoundly positive, leading to players and staff alike finding a spot in the NBA over a shared love of the sport.
During his time at the helm, Masai lead the Raptors to the 5th highest winning percentage in the NBA.
He brought the first championship that Toronto, that Canada, had seen in decades.
He gave sports fans across the nation a reason to cheer together between their shared laughter at the Leafs & beleaguered sighs at the Jays.
Most of all, he fulfilled Larry Tanenbaum’s vision of Canada as a whole being a basketball nation while fulfilling his own personal ambition of winning a championship.
He saw the Toronto Raptors win it all and though he may never be able to appreciate the glory the championship he brought due to a racist police officer ruining his achievement, banners hang forever. The memories created along the way will remain in the fanbase’s collective memory with fondness in all the years to come, the championship forever hanging in Scotiabank Arena regardless of what fortune has in store for the team’s future.
He may have had his share of hiccups in the final years, his team lacking in success in that same time. Still, there goes the best sports executive that Toronto has ever seen.
Here’s to the Giant of Africa and a man whose name should very well hang via a jersey in the rafters along with the legends of Toronto who won it all in 2019, Masai Ujiri.
