The Toronto Raptors are a team that has built a championship out of loyalty and internal development. Rather than chase some of the big names in free agency, the Raptors’ core is often made up of players they drafted, developed, or brought in with a very cheap deal in free agency.
Due to their geographic challenges, the Raptors have often needed to ensure that all of their best players are cared for and kept around longer than most teams would retain them. However, this philosophy has often led to them keeping players past their sell-by date.
Be it keeping veterans to the point where their trade value diminished to nothing or continuing to pray for a youngster to break out and become a star, these players went from integral parts of the Raptors to players the fanbase spurred on over the course of their tenure.
5 players the Toronto Raptors held on to for too long
5. Joey Graham
Selected just one pick before Danny Granger and well before All-Star David Lee and Monta Ellis in the 2005 NBA Draft, Graham never developed into the defensive force on the wing that many were expecting. However, this was by no means due to a lack of trying on Toronto’s part.
Graham managed to stick around for four seasons in Toronto, never averaging over 20 minutes per game or 7.7 points per game in any of those seasons. Still, his athleticism and defense kept convincing some thin rosters to take gambles on him, even if they did not work out.
The Toronto Raptors never made Joey Graham a star.
Graham had his chance to prove the Raptors wrong when he joined the Nuggets in the 2009 season, but he fell flat on his face and averaged just 4.2 points per game. The jumper never came around, though the Raptors certainly afforded him many chances.
Graham is just one name in a long line of mid-2000s Raptors picks that never quite became the stars they were billed as. In Graham’s case, it consisted of watching some gnarly basketball as a defense-first player tries and fails to score consistently in the pros.
4. Malachi Flynn
Flynn has already made it onto this list. After getting thrown into an impossible situation as a rookie due to the delayed NBA Draft and the whole Tampa sabbatical mess, Flynn looked like a very promising rookie after getting his feet under him in the second half of his debut season. Replicating that has proven tough.
Flynn’s minutes have stagnated at around 13 per game, and he is often limited to mop-up duty. A career 37% shooter from the field, Flynn has never been as efficient as he was in college. As such, replacing Fred VanVleet proved to be too difficult of a task for him to accomplish.
Malachi Flynn hasn’t thrived with the Toronto Raptors.
The Raptors could have bailed on him in a trade if they were so inclined, and doing so likely would have helped them get back a piece that could help them win now. Instead, they have let him waste away on the bench to the point where his value has essentially deteriorated into nothing.
When you’re coming into the NBA as small as Flynn, efficiency or excellent passing ability must be a prerequisite. Flynn has offered neither. While his handle is impressive, the Raptors may not be the best place for Flynn when it comes to carrying on his NBA career.
3. Bruno Caboclo
The “two years away from being two years away” draft night dig haunted Caboclo forever. After being picked No. 20 overall despite nary a mock draft even projecting him as a draftable player, Caboclo’s 6-9 frame and 7-7 wingspan was held in high regard by Masai Ujiri.
Even if he was not to contribute early, Ujiri could eventually reap the benefits once he figured things out. Unfortunately, the lightbulb never switched on, and Caboclo’s career stands out as one of the worst in recent memory for a first-rounder in terms of production.
Bruno Caboclo never developed for the Toronto Raptors.
Caboclo scored just 27 points in four seasons with the Raptors. DJ Wilson outscored him in four games with the Raptors, while Armoni Brooks and Goran Dragic can claim to have more impressive Raptors careers than him. Nevertheless, Toronto held onto him every year, hoping he would thrive.
Caboclo has a very brief stint as a rotation player with the Grizzlies before heading back to the international ranks. The Raptors seemed to be the only team in the league that was convinced that he could eventually become something, and they got burned by not getting something for him in a trade.
2. Michael Stewart
The fact that Stewart is not often mentioned among the worst free agent signings in NBA history is baffling, as the Raptors got almost nothing of value from him. After blocking 2.4 shots per game in his rookie season with the Kings, the Raptors signed him to a whopping six-year contract worth $24 million in 1999.
Stewart proceeded to show he was not an NBA player beyond that magical stretch with Sacramento. Averaging 1.4 points per game for that money is bad enough, but doing so while also playing 121 games for the franchise shows how desperate the team was to justify the contract.
Michael Stewart struggled for the Toronto Raptors.
Stewart somehow convinced three other teams to take a chance on him, but neither the Cavaliers, Celtics, or Hawks could get Stewart back to his Kings days. His career fizzled out after that, with his most prominent achievements coming during his first season.
Masai Ujiri might get some heat for keeping the team together too long, but at least he is holding on to remnants of a championship team. Stewart’s tenure with the Raptors was one of ineffectiveness and disappointment, etching him a place in the more infamous corners of the franchise history books.
1. Vince Carter
Carter is one of the greatest players in franchise history and was at the peak of his powers in the early 2000s. The mutual distaste that Carter and the Raptors had between each other at the time (it has since been patched up) became quite venomous, and it helped knee-cap a half-decade of Raptors basketball.
The feud between the two got nasty, and it very clearly bled onto the court, as Carter appeared to be checked out and giving 50% energy on a good day. Toronto inadvertently hurt his value by letting the trade saga spin out of control. The offer the Nets sent them was laughable.
Vince Carter should have been traded at peak value.
Carter was traded for Alonzo Mourning, but he refused to play for the Raptors. Aaron Williams, Eric Williams, and two picks don’t amount to a very good haul for a game-changer that remains all over the Toronto record books. Acting sooner could have helped Toronto get a much better haul.
While the Raptors did start the Chris Bosh era as a result of this trade, the team’s much-maligned depth alongside Bosh can be attributed, in part, to their feud with Carter, as they managed to tank his value, poison the well, and impact the team on the court.