The Toronto Raptors are about to begin their 29th NBA season, and there are plenty of questions surrounding the team. Pascal Siakam is entering the final year of his contract, and there has been no shortage of trade rumors. Toronto has missed the playoffs in two of the last three years, but they are closer than fans think to be being serious contenders.
Will the Raptors take a risk to get into title contention? It is not an easy decision, and Toronto may be eager to see how the roster fits after Fred VanVleet’s departure in free agency. Can they make a serious run in 2024? They will need some upgrades before February’s trade deadline if that is the franchise’s goal.
The Toronto Raptors are no strangers to taking chances on talent and watching it blow up in their faces. They have gambled on up-and-coming prospects and established veterans only to watch both backfire. What players do they regret taking a chance on?
Players the Toronto Raptors shouldn’t have gambled on
12. Fred Jones
Jones was the Pacers’ first-round draft pick in 2002, but he struggled to find playing time early on. His breakout moment came when the 6’4 guard won the Slam Dunk Contest in 2004. His production improved in the second half of his second NBA season, and Jones helped Indiana make three straight playoff appearances.
He was a restricted free agent in 2006, but the Pacers rescinded his qualifying offer, which cleared the way for the Toronto Raptors to sign him to a three-year deal worth $11 million. The 27-year-old should have been in the middle of his prime, but things did not work out.
Fred Jones lasted just 39 games with the Raptors before being traded to Trail Blazers. His minutes and production dropped off in Canada, and he was traded for Juan Dixon, who lasted just one year with the Raptors. Jones played two more years in the NBA before finishing his career overseas.
Giving the 6’4 guard a three-year deal immediately backfired on the Raptors, but it is far from the worst gamble they have taken in their first 28 years as a franchise.
11. DeMarre Carroll
Carroll was a late first-round draft pick in 2009, but he struggled to find a consistent role early on. The 6’6 wing showed flashes during his first four seasons in the league, but it was not until he joined the Hawks in 2013 that he blossomed. Carroll was a starter on the wing on back-to-back playoff teams, including in 2015 when they reached the conference finals.
Carroll became a free agent after that run. He was right in the middle of his prime, and he agreed to a four-year $60 million deal with the Raptors. The 6’6 wing was a key rotation option, but his new contract made him the 41st highest-paid player in the 2015-2016 season.
He struggled to stay healthy in year one, and his efficiency dropped off significantly. Still, the Raptors reached the conference finals. Carroll did not make the same impact in Toronto. In year two, his production slipped further, and it became clear the Raptors needed to move on.
Toronto had to trade one first-round draft pick and one second-rounder to Brooklyn for the Nets to take on Carroll’s contract. It was a disastrous signing, and the 6’6 admitted to not fitting into the Raptors’ iso-heavy offense after his departure. It was a move fans would love to forget happened.
10. Rafer Alston
Alston is a New York City legend that spent many days dominating at Rucker Park. The 6’2 guard made the transition from streetball to the NBA, but it was a slow start. He spent his first three years in Milwaukee but never played more than 13.4 minutes per game. After a brief stint with the Warriors where he never appeared in a game, Alston signed a rest-of-season contract with the Raptors in 2002.
He was the team’s backup point guard for 47 games, and it opened more opportunities. Alston was in his prime and signed with the Miami Heat in 2003 where he averaged over 21 minutes per game for the first time and proved he could be a key rotation piece. The following offseason, the Raptors needed a point guard, so they inked Alston to a six-year contract worth $29 million.
His second stay only lasted one season. The Raptors won seven more games than the previous year, but they still missed the playoffs. Alston had arguably the best statistical year of his career as he started 78 of his 80 games played and averaged 14.2 points, 6.4 assists, and 1.5 steals in 34.0 minutes per game, but there were behind-the-scenes issues that prompted his short stay.
Rafer Alston was traded for Mike James in October 2005. James lasted just one season in Toronto, but he too had arguably the best year of his career with the Raptors. It was disappointing to see the streetball legend exit so quickly after signing a massive contract, and Toronto likely regretted the deal.
9. Michael Stewart
The original gamble on Stewart was worthy. He went undrafted in 1997 after four years at Cal. The 6’10 big man was an elite shot-blocker in college, and he had a strong rookie season with the Sacramento Kings before becoming a free agent. The Raptors were coming off a 16-win season in 1998 when they signed Stewart to a one-year $1 million contract.
The 23-year-old barely played, but Toronto won seven more games. They believed in his talent and rewarded him with a six-year deal worth $24 million. The Raptors hoped Stewart would blossom into a key piece of their first playoff team, but the contract turned into an absolute disaster.
The 6’10 forward never played more than 24 games in a season and his 9.4 minutes per game in his first season in Toronto turned out to be his best. He never scored more than 2.0 points each night before he was traded to the Cavaliers in a six-player deal in 2003.
Michael Stewart was on the roster for the Toronto Raptors’ first three playoff appearances but only played a total of 14 postseason minutes in his career. The franchise took a shot on a young talent, and it did not pan out. Toronto regretted it as they agreed to pay $25 million for 174 points and 999 total minutes over four seasons.
8. Jermaine O’Neal
The Raptors were coming off back-to-back first-round playoff exits when they traded the 17th overall pick in the 2008 draft, T.J. Ford, Rasho Nesterovic, and Maceo Baston for O’Neal and the 41st selection. It was a massive gamble, but Bryan Colangelo dreamed of Bosh and O’Neal being the perfect frontcourt pairing that pushed Toronto to new heights.
The six-time All-Star lasted just 41 games with the Raptors. He was starting to decline but still produced strong numbers as he averaged 13.5 points, 7.0 rebounds, and 2.0 blocks in 29.7 minutes per game. The frontcourt fit was not ideal and the Raptors were near the bottom of the Eastern Conference standings when they traded O’Neal to Miami in February. It cost them two draft picks and Jamario Moon to get Shawn Marion and Marcus Banks.
Jermaine O’Neal played five more years in the NBA before retiring in 2014. His time with Toronto was certainly forgettable, but it was just the beginning of a rough stretch for the Raptors. Chris Bosh left in free agency in 2010, and the franchise missed the playoffs five straight years.
Toronto Raptors fans are more scorned by this trade because the Pacers selected Roy Hibbert with the 17th pick, who was arguably a better fit next to Chris Bosh and could have changed things in Toronto.
7. Linas Klieza
Klieza was a first-round draft pick in 2005 out of the University of Missouri. The Lithuanian forward became a key role player and helped the Nuggets reach the Western Conference Finals in 2009, but he decided to return to Europe where he helped Olympiacos reach the EuroLeague Final Four the following year.
The Raptors had just watched Chris Bosh leave in free agency, and they needed talent, so Toronto signed Klieza to a four-year contract worth $20 million to bring him back to the NBA that quickly turned sour.
The 6’8 forward struggled to stay healthy and his production steadily declined when he was on the floor. Klieza’s best season in Toronto was his first where he averaged 11.2 points and 4.5 rebounds in 26.2 minutes per game. He never played more than 49 times in one season, and things got so bad that the Raptors used the amnesty clause on him before the final year of his deal.
Linas Klieza played his final NBA game with the Toronto Raptors. He returned to Europe after being let go where he played two more seasons before hanging up the sneakers. The 6’8 forward was an overpaid role player that could not stay healthy during his time in Toronto, which made cutting ties with him and avoiding the luxury tax an easy decision in 2013.
6. Jason Kapono
Kapono was the second pick in the second round of the 2003 draft, and it took a few years and three different teams before the 6’8 forward broke out.
He was playing for the Heat in his fourth season where he averaged 10.9 points in 26.4 minutes per game while shooting 49.4 percent from the field and an absurd 51.4 percent on his 3-point attempts. The Heat were swept by the Bulls in the first round of the playoffs, and Kapono barely played, but that did not stop him from scoring a life-changing contract in the 2007 offseason.
The 6’8 forward earned a four-year $24 million, which was the full mid-level exception back in 2007. He continued to be an elite shooter, but he did not fill a need in Toronto. Kapono’s defense was porous and his offensive production dropped off. He played his best in the 2008 playoffs, but the Raptors were bounced by the Magic in the first round.
Toronto dipped in the standings in 2009 before trading Jason Kapono to the Philadelphia 76ers in the offseason. He shot the 13th-best 3-point percentage in NBA history, but his contract was a regret for the Toronto Raptors. They needed shooting, so it made sense for Bryan Colangelo and the team. Sadly, Kapono was just so one-dimensional that things did not go as planned.
5. Jerryd Bayless
The Raptors made a regrettable trade in Nov. of 2010 as they shipped out Jarrett Jack and two role players for Bayless and Peja Stojakovic. Jack was the team’s starting point guard, but Toronto was ready to move on after Chris Bosh departed for Miami in free agency. They got Stojakovic, who lasted just two games with the Raptors before being waived only for the 6’10 forward to play a key role on the Mavericks title squad later that season.
Bayless was the prize of the deal for Toronto, but he was primarily the backup point guard behind Jose Calderon. The 6’3 guard had flashes of brilliance and plenty of head-scratching moments during his season and a half with the Raptors. He had two 30-point games and 18 times where he scored two or fewer points.
Bayless was never short on confidence, and it was clear that it was time to move on. An oblique injury limited him to just 31 games in the 2011-12 season, and the Toronto Raptors let him walk in free agency the following offseason. They were ready to get off the roller coaster ride that was the 6’3 guard’s play.
Giving up Jarrett Jack to get Jerryd Bayless was a regrettable move for the franchise. Over the next five years, Jack averaged 12.2 points and 5.2 assists in 29.7 minutes per game as his team made two playoff appearances. Bayless produced 9.1 points and 3.1 assists in 23.6 minutes per game but was the Grizzlies’ backup point guard during their 2013 run to the conference finals.
4. Landry Fields
Fields was a second-round pick by the Knicks in 2010, who immediately cracked the starting lineup and was a key rotation player on back-to-back playoff teams. The 6’7 wing entered free agency at 24 years in 2012. Most expected him to return to the Big Apple where he had become a fan favorite, but the Raptors came in with a massive offer sheet.
Toronto’s three-year contract worth $20 million was too much for the Knicks to match, but the Raptors quickly wished they had. Field’s production slipped in his second year in the Big Apple, and the drop off continued after he arrived in Toronto. His first year with the Raptors was his best as he averaged 4.7 points, 4.1 rebounds, and 1.2 assists in 20.3 minutes over 51 games.
Fields played just 107 games over the three years. A nerve issue cost him most of the time, and he is still dealing with (subscription required) it. The 6’7 wing’s jumper vanished and so did his playing career. Fields was just 26 years old when he played his final NBA game as he went from a promising prospect to out of the league over his three years with the Raptors.
Landry Fields is currently the general manager for the Atlanta Hawks, but the Toronto Raptors certainly regretted signing the restricted free agent back in 2012.
3. Alonzo Mourning
The Raptors traded Vince Carter to the then-New Jersey Nets in 2004. In return, they got two first-round draft picks, two bench players, and a future Hall of Famer. Mourning was a seven-time All-Star and one of the most dominant big men in the league before missing the 2002-03 season with kidney disease. He only played 12 games the following season, but there was still hope the 34-year-old would be an impactful option.
Mourning wanted out of New Jersey, but he was unwilling to come to Toronto. The two-time Defensive Player of the Year did not play one second for the Raptors. Toronto tried for two months before eventually waiving him. He returned to the Miami Heat and helped them win the championship in 2006.
The Raptors got fleeced in the Vince Carter trade. They gave up one of the league’s best players, and Alonzo Mourning refusing to report made it worse. The return shrunk to two bench players and two first-round picks. Yes, Vinsanity wanted out, and Toronto had to trade him, but Mourning made the return even more disappointing and quickly became a villain to Raptors fans.
It was not the first time the Toronto Raptors gambled on an aging center only to be filled with regret.
2. Hakeem Olajuwon
Olajuwon is an all-time great and one of the best centers in NBA history. The 12-time All-Star led the Rockets to two championships as he twice led the league in rebounds and made nine All-Defensive teams. The Dream was no longer an elite big man when he arrived in Toronto, but nobody expected the sign-and-trade to completely blow up in the Raptors’ face.
Olajuwon got a three-year $17.4 million from Toronto as a 38-year-old in 2001. Vince Carter was in his prime, and the Raptors had made two straight playoff appearances. They thought The Dream could help them get over the hump, so they gave the Rockets two draft picks, including a first-rounder for the future Hall of Famer.
Olajuwon only played one season with the Raptors where he averaged a career-low in points, rebounds, and blocks per game. He was clearly past his prime and only able to play 22.6 minutes per game. The Dream struggled mightily in the playoffs as the Raptors exited in the first round. Those would be his final games as a back injury forced him to retire in 2002.
The Toronto Raptors dreamed of having an elite defensive anchor that could help push them to the next level, but Hakeem Olajuwon did not have enough left in the tank. The three-year deal turned into a disaster and one that haunted the franchise as they began a rebuild in 2002.
1. Hedo Turkoglu
Turkoglu was a first-round draft pick in 2000, but it wasn’t until he arrived in Orlando in 2004 that he broke out. The 6’10 forward quickly became a starter and key contributor as the Magic became a force. They reached the NBA Finals in 2009 with Turkoglu as their third-leading scorer and top playmaker in the postseason.
The 30-year-old became a free agent after that run, and the Raptors were eager to improve their roster as they tried to convince Chris Bosh to stay. It resulted in a four-team sign-and-trade that brought Turkoglu to Toronto for Shawn Marion, Kris Humphries, Nathan Jawai, and one second-round draft pick. The newest Raptor also got a fresh five-year $53 million contract, which instantly turned into a disaster.
Turkoglu’s production dropped off across the board as the Raptors missed the playoffs for the second straight year. The 6’10 forward quickly asked to be traded, and he was sent to the Phoenix Suns for Leandro Barbosa and Dwayne Jones just one year after arriving in Toronto.
The Toronto Raptors quickly regretted signing Hedo Turkoglu, and matters quickly went from bad to worse when Chris Bosh left in free agency in 2010. It was one of many unfortunate moves by the team’s front office. Who will be the next player to make this list? Stay tuned to find out.
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