1. Isiah Thomas was the first president and general manager of the Raptors and probably the wisest and most conspiratorial basketball man Toronto has ever known. Thomas drafted Damon Stoudamire, Marcus Camby and Tracy McGrady in three short years, and in between that he tried to buy the team, tried to destroy the franchise, and that kind of confusion became something of a Raptors theme in the early years of the franchise.
2. Vince Carter is the most exciting player in Raptors history. There isn’t really debating that. He was half man, half amazing, but if there was another half, it would be half cheat. He brought more attention to the fledgling team than anyone in history, became sure-thing television viewing on ESPN with his array of dunks, and almost brought the Raptors somewhere Almost. And when things didn’t go his way, he did the Isiah and little kid thing — he took his ball and went home.
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3. Kyle Lowry almost quit on himself, but that was before he met Masai Ujiri, who tried to trade Lowry in his early days of running the Raptors. Lowry had NBA talent but needed an adjustment in attitude which was supplied partially by Ujiri. Once, the adjustment was made, Lowry played his way to a key part of a championship team, a certain Hall of Fame career and the next player after Carter to get his jersey retired.
4. Kawhi Leonard is the most accomplished player the Raptors have ever had. But he was here for only one season. One championship season. One amazing, unforgettable, country changing run. And then it was over. Just like that. Life returned to normal. The Raptors have won just one playoff round since Kawhi left for the Los Angeles Clippers, but in fairness, the Clippers have only won three in those five seasons. If only Kawhi had decided to stay. If only.
5. Bryan Colangelo was fired as general manager of the Raptors, essentially because MLSE CEO Tim Leiweke couldn’t understand why a basketball man of any credibility running a weak team would trade its first-round pick for a player such as Lowry. “Who would do that?” Leiweke once said to me. Colangelo did some great things for the Raptors like dealing for Lowry and hiring Dwane Casey to coach, but unlike other Raptors before him, his bigger problems started after he left Toronto.
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6. Andrea Bargnani was the only Raptor picked first overall in the NBA Draft. Nothing was more Raptor than finishing last in a year in which there was no marquee player available. There was no Auston Matthews waiting for the Raps.
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arrived in Toronto from the Denver Nuggets and promised a championship on the day he was introduced as general manager. And he delivered. Who does that? It took huge stones for Ujiri to deal the popular DeMar DeRozan to bring Kawhi to Toronto. Especially not knowing if Leonard would ever report to play here. Leonard did report, made the largest shot in Raptors history, and Ujiri had his championship. Something we may never see again in this city. Ujiri is the impetus behind We The North and so many other causes that matter. At times it has been He The North with Ujiri. He is that strong and forthright a leader.
8. All Chris Bosh did was his job. He wasn’t fancy or flashy or in any way difficult. He was never loved or disliked by fans, somewhere in the middle really and few have a called for his jersey to be retired, even though he spent seven of his 13 NBA seasons here and is in the Basketball Hall of Fame.
9. Charles Oakley only played three of his 19 NBA seasons for the Raptors, but left an impression so large he is still talked about regularly by media, management and some players. Oakley was a tough physical guy of minimal offensive skills who understood what it took to win and what was absolutely necessary. How do you find the next Oakley? May not be possible.
10. Brendan Malone was fired after the first season as the first coach of the Raptors and typical of the early years it was handled badly. Malone, though, couldn’t officially say a word about what happened to him. He signed a non-disclosure clause upon reaching his settlement. About an hour after saying he couldn’t talk, the phone rang at my desk at the Toronto Sun. It was Mrs. Malone calling. “I didn’t sign anything,” she said, going on to detail so much of what went on in Toronto’s initial season.
11. Larry Tanenbaum’s rise to prominence as an NBA owner and sporting magnate is one of the great success stories in Raptors history. He tried to buy an existing NBA team before the league expanded to Toronto and Vancouver, was originally turned down by the board of governors in favour of John Bitove when the team was awarded to the city and ironically, as a minority owner, wound up as chairman of the board of the NBA, where he currently remains.
12. John Bitove found the land where Scotiabank Arena sits, devised a plan for a basketball only arena, and that was before he sold his interests and MLSE was born. Who knows where Toronto’s arena would be today had it not been for Bitove’s foresight?
13. Little known Jack Armstrong brought life to basketball broadcasts with his loud, unusual, raspy voiced, his Brooklyn toned Jack-isms. Every Thursday when we take the garbage out around our house, we say: Get that garbage outta here. He’s one of ours now. Has been that for a long time. Fits like a pair of old comfortable shoes anytime talking hoops.
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14. Pascal Siakam was a fascinating study in his time in Toronto. He wasn’t a star, then he was, then he wasn’t, then he was. It depended on the year, the moment, the circumstance. He loved the team and the city until it was time for divorce. Sometimes even amicable relationships based on love can end badly.
15. Nick Nurse became the accidental coach of the Raptors. Management wanted Mike Budenholzer but he went to Milwaukee to coach. Instead they settled on the career minor leaguer Nurse and he was hired before Ujiri traded for Kawhi Leonard. Nurse coached his way to prominence and an NBA championship as a rookie and will always be remembered for that. That championship win has set him up financially for life.
16. Dwane Casey brought the Raptors from nowhere to somewhere. He wouldn’t tank when they wanted him to tank.
He wanted to teach and coach and get better incrementally. Most of his players over time went on to win an NBA title without him. There may have been finer people associated with the Raptors over the years than Casey, but I can’t think of one at this time.
17. Wayne Embry is a walking, talking encyclopedia of sports and American history. He was the first African American GM in professional sports in North America. He traded Lew Alcindor before he became Kareem Abdul-Jabbar. All that came after he starred as an NBA player, rooming in Cincinnati with the great Oscar Robertson. He has been a Raptors advisor since 204 and he has brought along a conscience and sensibility that is necessary for any franchise. If he had a number here, it would have been retired by now.
18. DeMar DeRozan has played the most games in Raptors history, the most minutes, taken the most shots, missed the most shots, hit the most three throws and brought a sense of professionalism with him every day and every season he was here. It will take years for anyone to come close to his all-time Raptor records. In the future, DeRozan will sign one of those fake one-day contracts to announce his retirement as a Raptor. Unlike so many other stars, he never wanted to leave.
19. Glen Grunwald, who played with Isiah Thomas at Indiana, didn’t draft Vince Carter although there are people who still believe that Carter was a Raptors pick. He was one of those NBA draft flips that happen on draft night and Grunwald traded Antawn Jamison and cash for Carter. The second greatest trade in Raptors history. The cash being important in this case. It paid for a Raptors practice facility they couldn’t at the time afford.
20. Bobby Webster might be the lowest profile general manager in all of sports and he wouldn’t have it any other way. He likes nothing better than to be invisible. But for the past seven years, he has been the Raps GM. His fingerprints involved with acquiring Kawhi, Marc Gasol and the dealing away of O.G. Anunoby. Webster doesn’t talk, he whispers and only to a selective few.
21. B.J. Tyler was selected in the expansion draft from Philadelphia was thought to be someone who get a lot of playing time in the early years of the franchise. Turns out, he got none. Never played a game. Tyler accidentally fell asleep with an ice pack on his ankle in training camp, causing him severe nerve damage and ending his NBA career.
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22. Sam Mitchell coached the Raptors for five seasons, almost fought Vince Carter, argued and cajoled with media, had nicknames for many, and was genuinely a lot of fun to be around on a daily basis. He has since turned to television where he works Raptors games and various U.S. outlets employing his snark and his analysis, political and otherwise.
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23. If there was an all-time Raptors team there would probably be a place for the power forward Antonio Davis. He was a complete NBA player who wasn’t as complete when it came to his lack of understanding of Canadian television and the Canadian schooling system. He was also married to Kendra, best known around here for leaving filthy voice mail messages on the answering machines of some media members.
24. It was late in the afternoon on trade deadline day, maybe trade deadline night, when the Raptors announced in 2019 they had acquired Marc Gasol from Memphis. Gasol had been an NBA fixture before arriving here, but he brought two things to the Raptors. One, an innate understanding of what it takes to win and a defensive acumen that enabled the Raptors to beat Philadelphia in Round 2 of the playoffs. Gasol was more than a basketball player, he was a humanitarian of significance.
25. OK so I’m cheating here. This is five for the price of one here. Butch Carter, Kevin O’Neill, Lenny Wilkens, Jay Triano and Darrell Walker all coached the Raptors, some better than others. Mostly without much notice. The Raptors have made the playoffs in 16 of their 29 seasons, missed in 13.
26. Chris Childs forgot the score. That’s happened before in NBA games. But in a playoff game — late in the fifth game of a best of five playoff series in 2002? Raps trailed Detroit by three points. Childs thought they were four points behind. Needless to say, the game and the series didn’t end up well for Toronto. That was Childs’ last game as a Raptor. He did go on to play 12 more games in New Jersey.
27. The fans in Toronto didn’t want Damon Stoudamire. They wanted Ed O’Bannon. Which is why you shouldn’t often listen to fans. Stoudamire was the first Raptors draft pick ever, went on to win rookie of the year, should have gone on to a long and distinguished career in Toronto. But his time here was poisoned by Isiah Thomas and Stoudamire, years later, regretted orchestrated his departure from the city.
28. There are many ways to describe Scottie Barnes, but the terms Masai Ujiri likes best is gym rat. Raptors fans would prefer something else — Toronto’s next superstar. It’s not yet known if Barnes will become what the Raps need him to become, but his salary says mega-star. Now it’s just a matter of Barnes living up to his large billing.
29. The Raptors have had so-so players and so-so teams and so-so coaching over the years — but what they’ve never had is a so-so mascot. Not for a single night. The guy inside The Raptor outfit has delivered game in and game out for more than three decades. Kids love him. Adults love him. He understands what’s expected of him and brings it every game. If there’s a better mascot in the NBA, I haven’t seen one.
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