The Toronto Raptors don't have the same long and storied history as teams like the Los Angeles Lakers and New York Knicks. They are one of the league's youngest teams, joining the NBA as an expansion team in 1995. They have logged just 29 of the NBA's 78 seasons.
Unfortunately, that hasn't spared the Raptors from a lot of heartache and betrayal over the years. One of the worst parts of sports fandom is when a beloved player turns their back on a team. That commonly looks like walking in free agency, but it also includes trade demands and suspensions. It's not limited to players, either; coaches and general managers can hurt a team as well.
Let's illustrate the point by taking a stroll through Raptors history, highlighting 10 times a player or executive turned their back on the team, whether that move was merely hurtful or outright devastating. Buckle up, for those 29 seasons have generated a lot of painful memories for the Raptors and their fans.
No. 10: OG Anunoby
Let's ease into our list with the mildest example of a player turning their back on the franchise. OG Anunoby was an unquestioned draft success by the Raptors' front office, who snagged the Indiana forward one pick before the Denver Nuggets in the 2017 Draft; imagine the "what if" if the Nuggets had landed an All-Defense Candidate instead of Tyler Lydon, a forgettable draft bust.
Anunoby developed into a strong two-way forward with a consistent 3-point stroke and all-league defense; his combination of size, speed and strength made him perfect to deploy on all manner of opponents. At 26 years old the Raptors could have kept him around this year and made him a key part of their core moving forward.
Yet as the Raptors pondered their options during trade season, Anunoby reportedly was ready for a change of scenery, and he let management know how he felt. Toronto proceeded to move him in a trade to the New York Knicks in a move that brought back a pair of young players but no first-round picks.
A quiet trade request is not as painful as it could be, but he was yet another player ready to move on from the 905. If he had communicated that he wanted to be a part of what the Raptors were building, he would almost certainly be on the team right now and forming a dynamic pairing with Scottie Barnes. Instead, he is out the door, another departed Toronto player.
No. 9: Jalen Harris
The Raptors drafted Jalen Harris late in the 2020 NBA Draft. He had something of an inspiring story, bouncing back from a broken back to establish himself as one of the best players in his conference at Nevada before entering the draft and joining Toronto for the COVID-delayed 2021-22 season.
The 6'5" shooting guard shot the lights out in the G League and earned some late-season run with the top squad. That included four consecutive double-digit scoring outings late in the season, including a 31-point explosion against the Dallas Mavericks. The young rookie looked like the latest draft find for the organization.
Then it all came crashing down. That summer he was suspended by the NBA for violating the NBA's anti-doping program. He was out of the league for a full year, then when he returned he could never catch on with a team; he wouldn't play another NBA minute after that breakout rookie season. His 31-point game, in fact, would be the last one he would ever play in the league.
The pressure on players that often push them to PEDs is a complicated conversation, but Harris went from an exciting rookie on the rise to being entirely unavailable to the team. Whatever the cause, the outcome was a player unable to help the team.
No. 8: Serge Ibaka
The Toronto Raptors made a big swing to upgrade their frontcourt in 2017, trading the sharpshooting Terrence Ross and a first-round pick to the Orlando Magic for Serge Ibaka. The 6'11" big man had excelled alongside Kevin Durant and Russell Westbrook on the Oklahoma City Thunder for years and was one of the league's premier shot-blockers. The hope was that he could bolster the backline and make up for shaky defense on the wing from players like DeMar DeRozan.
The results were perhaps not as dominant as the Raptors had hoped, but Serge Ibaka certainly made an impact. The Raptors ranked 25th, 11th and 11th in defensive rating in the three seasons preceding his arrival; they ranked 5th, 5th and 2nd the next three seasons. While he ultimately came off the bench by the time Toronto's Finals run began in 2018-19, he played a critical role on the only championship team in franchise history.
Ibaka hit free agency a year later, and the Raptors made it clear that they wanted to bring both Ibaka and Marc Gasol back to maintain their veteran big rotation. That ultimately did not happen, as Serge Ibaka signed a two-year contract with the LA Clippers.
Why did Ibaka leave? It wasn't due to playing time, or a fracture with the front office or head coach. In fact, Ibaka claimed that "he didn't want to leave" but had to. The reason? The Clippers paid him more money.
Ibaka's decline was about to come, so perhaps he was right to secure the largest bag that he could have, but it's a tough move when a veteran player leaves the team he won a title with simply for a slightly larger payday. He chose money (and not even much; he made only $19 million over two seasons) over the Raptors.
No. 7: Isiah Thomas
The Toronto Raptors never had to face Isiah Thomas and the Bad Boy Pistons; they came around after that era of basketball was over. They never had to see their beloved players clotheslined, grabbed, punched or tossed to the floor. The Pistons had a well-earned reputation and it ultimately brought them two NBA Championships and one of the most iconic names of any team in basketball history.
The floor general and best player on those teams was Isiah Thomas, and the point guard didn't end his connection with the NBA when an Achilles injury ended his career. In his retirement speech in May of 1994, he simultaneously announced the end of his playing career and the start of his front office career as the new Executive Vice President of the expansion Toronto Raptors franchise.
Thomas was essentially the "star" of the Raptors when they launched a year later before they could build an on-court identity of their own. Thomas proved himself a savvy evaluator of talent, especially in the draft, and under his oversight the Raptors drafted Damon Stoudamire, Marcus Camby and Tracy McGrady in consecutive years.
Then in 1997, Thomas made a push to gain a controlling ownership stake of the Raptors, seeking to build on his fame and success by becoming one of the NBA's governors. His move didn't work, and it immediately soured his relationship with the team's other owners. Just a few months later Thomas would leave the team, setting off a chain reaction of events. The Raptors had an abysmal season, star guard Stoudamire clashed with the team until he was dealt to Portland, and GM Glen Grunwald became the lead decision-maker and didn't handle his tenure well (more on that momentarily).
Thomas was exactly what the team needed to begin its life, a famous face to draw interest and a keen player evaluator. Yet whether he received bad advice or it was always in his nature to grab for more and more power (his history since suggests the latter) his emotional, complicated and violent departure from the team sent the franchise into a tailspin just when things were looking up.
No. 6: Glen Grunwald
Glen Grunwald was a high school All-American and the captain of an Indiana University team that won the National Championship. That Hoosiers team was led by a dynamic point guard named Isiah Thomas, and years later when Thomas took the job running the Toronto Raptors, he brought Grunwald with him as his No. 2.
When Thomas' power play failed in 1997 and he left the team, Grunwald was left to try and hold things together, and he failed miserably. Rather than find a way to reconcile with star Damon Stoudemire, who was upset at Thomas' departure, Grunwald traded him at midseason. That caused head coach Darrell Walker to quit in protest, and a Raptors team without its leader and coach spiraled to a 16-66 record at the bottom of the standings.
Grunwald completed the trifecta that summer, trading promising big man Marcus Camby, who would go on to be a difference-making defender elsewhere. In just six months the Raptors completely reset, halting their momentum as a franchise and effectively going back to square one. Much of that blame is on Thomas' shoulders, but Grunwald bears a lot as well.
To Grunwald's credit, he then took the pieces of that team and built up the Raptors' first playoff team, adding Vince Carter as the centerpiece and building around him. Toronto even won a playoff series in 2001.
Then he did it again. The Raptors were plagued with injuries in 2002-03 and missed the playoffs, and Grunwald began another frenetic teardown. He replaced the head coach, traded away starting center Antonio Davis and took a good team and sent them spiraling back into the lottery, a chaotic destruction that led to Vince Carter demanding a trade out, and Grunwald being fired before the 2003-04 season even ended.
Grunwald's inability to handle a team in adversity and his propensity to pull the ripcord instead of sitting in the tension of adversity and leading his team out of it, are why he appears on this list of people who turned their back on the Raptors.
No. 5: Fred VanVleet
Fred VanVleet is the ultimate NBA success story. A college star for mid-major Wichita State, VanVleet went undrafted in the 2016 NBA Draft; not a single team thought that his combination of playmaking and shooting was worthy of a draft selection. 5 players selected never played a single NBA minute, while another 13 played fewer than 30 games.
VanVleet, on the other hand, has played 471 games and counting, the first 417 of those with the Toronto Raptors franchise who gave him a shot and quickly empowered him with minutes and possessions. His 16.2 VORP ranks third in the draft class behind only longtime teammate Pascal Siakam and Domantas Sabonis. The Raptors found themselves a gem.
The memorable moments will be forever emblazoned in the memories and hearts of the Raptors and their fans. He and his wife welcomed a child into the world during the 2019 playoffs, and he returned and absolutely destroyed the Milwaukee Bucks, shooting 14-for17 (82 percent) from 3-point range over the final three games, all Toronto wins. Or when VanVleet made the All-Star Game, only the fifth undrafted player in NBA history to do so.
When Fred VanVleet reached unrestricted free agency in the summer of 2023, the Raptors made an offer to retain him, perhaps hoping their shared history would convince him to take a slight discount to remain with the franchise and oversee their retooling. Instead, VanVleet took a greater paycheck to oversee the rebuilding Houston Rockets' step forward.
In doing so, he left the franchise that had believed in him enough to give him a chance, and left behind a lot of shared history. That's a hard reality for Toronto fans to stomach.
No. 4: Kawhi Leonard
Three things can be simultaneously true. First, star players almost never leave a team with which they just won a championship. Secondly, Kawhi Leonard joined the Raptors via trade in 2018 and all parties involved assumed it was a one-year rental, even if most hoped for more. Finally, if given the chance to do it all again, Toronto and its fans would do it all over again.
Leonard and the San Antonio Spurs organization were feuding in 2018 and it led to Gregg Popovich and the Spurs trading the 2014 NBA Finals MVP that summer. With Leonard's health in question and on an expiring contract, the Spurs didn't look for a godfather offer of picks and prospects, instead accepting Toronto's relatively mild trade offer: All-NBA wing DeMar DeRozan, center prospect Jakob Poeltl, and a single first-round pick expected to fall at the end of the draft.
With Leonard (and the sharpshooting Danny Green) in tow, the Raptors surged through the regular season and fought their way through three consecutive difficult foes. They took down the Philadelphia 76ers in seven games, including the most iconic shot of Leonard's career, the buzzer-beating corner 3 that bounced on the rim four times before dropping. Then the East-leading Milwaukee Bucks went down in six. Finally, Leonard led the Raptors over the injury-riddled defending champion Golden State Warriors to win the first championship in franchise history.
The Raptors had a great mixture of established veterans and young rising stars who could keep the window open. Leonard could have returned to Toronto and competed for another title; they may even have been the favorites the following season with Kevin Durant leaving the Warriors. Everyone hoped Leonard would return and defend their title.
Instead, he walked out and joined the LA Clippers, where he has won only three playoff series (one of which he was injured for) and never sniffed the success that he had in Toronto. He always wanted to return home to play, and at the time of writing the Clippers are legitimate title contenders, but it will always be an open question as to what he and the Raptors could have accomplished had they stayed together.
No. 3: Chris Bosh
When the Toronto Raptors fell apart due to injuries in 2003, the consolation prize was the fourth overall pick in the absolutely-loaded 2003 NBA Draft. LeBron James went first to the Cleveland Cavaliers, Carmelo Anthony third to the Denver Nuggets, and Dwyane Wade fifth to the Miami Heat. The Raptors used their pick on Georgia Tech big man Chris Bosh. Those four players would combine for 54 All-Star appearances, including 11 for Bosh.
Bosh was an All-Star by his third season, averaging 22.5 points and 9.2 rebounds per game as he took the mantle of the team fully on his shoulders. The following season he finished seventh in MVP voting and led the Raptors back to the playoffs. He would play seven seasons with the Raptors, averaging 20.2 points, 9.4 rebounds and 1.2 blocks per game.
Bosh ranks third all-time in Toronto in career scoring; only Kyle Lowry and DeMar DeRozan scored more. His 4,776 rebounds rank first in franchise history, as do his 500 blocks. More than just his production, however, Bosh's intensity and dinosaur-like profile made him part of the fabric of Toronto basketball; he looked like a player who could stay with the Raptors for a very long time.
Then came the summer of 2010, when Bosh teamed up with James and Wade with the Miami Heat to form the league's boldest "super team" of three All-NBA players in their primes. Bosh became the perfect complement to his ball-dominant co-stars, reinventing himself as a stretch-big and defender who unlocked the Heat's ceiling, and they would go to four-straight NBA Finals and win two titles, a bittersweet outcome for Raptors fans.
No. 2: Tracy McGrady
Say whatever you want about the Toronto Raptors during their first handful of years in the league, but they absolutely knew how to draft. Damon Stoudemire, Marcus Camby, Vince Carter and Tracy McGrady were the team's first four first-round picks, all hits.
That also was part of the problem, however, as the Raptors in the late 1990s had a pair of shooting guards who both deserved minutes and opportunities. Vince Carter joined the team a year after McGrady and immediately started, winning Rookie of the Year and even receiving an MVP vote, then made an All-NBA team the following year.
That relegated rising star McGrady to a second-fiddle role, and it wasn't one he was comfortable filling. The idea of T-Mac and Vinsanity pairing up and destroying the Eastern Conference was a tantalizing one; both were athletic scoring wings who brought it on defense as well, and the two could have found a way to coexist on the wing. In McGrady's own words, in fact, he believed they could have contended for championships.
Instead, McGrady hit free agency in 2000 and booked it out of town, signing with the Orlando Magic. He became a perennial MVP candidate and twice led the league in scoring, although he never made it out of the first round of the playoffs. Carter and the Raptors would win a series even without McGrady; imagine what could have been if they had stayed together?
Instead, McGrady left for more touches and ended up regretting his Toronto departure.
No. 1: Vince Carter
Kawhi Leonard led the Raptors to a championship. Kyle Lowry's longevity likely makes him the best player in franchise history. DeMar DeRozan and Chris Bosh reached high individual heights. Yet no player in the history of the Raptors reached the same peak as Vince Carter.
One of the best athletes in NBA history, Vince Carter was unstoppable from the moment he stepped on an NBA court. He received MVP votes as a rookie, one of the last players to do so, and averaged 25.7 points per game in his second season. He made six-straight All-Star games (there was no All-Star Game his rookie season), led the Raptors to the playoffs for the first time in franchise history, and averaged 23.4 points per game, the most of any player who played multiple seasons for Toronto.
What's more, Carter wasn't just a star for the Raptors; he was one of the league's most marketable stars, period. His Dunk Contest explosions and in-game detonations made him an easy fan favorite, and he was a nightly part of highlight packages. He also starred for Team USA, famously destroying an opposing player by leaping clear over his head en route to a thunderous dunk.
It was a glorious partnership...until it wasn't. Things got ugly fast between Carter and the Raptors organization. There were public comments, private outrage, and even allegations that he was tipping endgame plays to opponents to sabotage his team's success.
It reached a breaking point when Carter told the Toronto Star newspaper that he wanted to be traded, even posting a letter to his website that he wasn't going to stick around while the team rebuilt. The Raptors blustered like they were going to force Carter to stay, but in the end, the star player got his way, as they almost always do. Early in the 2004-05 season, the Raptors traded Carter to the New Jersey Nets, then pivoted to rebuilding around rookie Chris Bosh.
Vinsanity was a cultural phenomenon and the best player that the Raptors had ever seen to that point. Rather than try to build them up, Carter forced his way out of Toronto and sought out success elsewhere, turning his back on a franchise that absolutely adored him. His messy departure is the most painful desertion in franchise history and tops our list of Raptors who turned their backs on the team.