The Six Biggest Trades in Toronto Raptors Franchise History

Toronto Raptors Trades

The Toronto Raptors have been a model franchise in the 2010s. A big part of that was the trades they made within the last 10 years. Therefore, five of the top six trades in Raptors’ history are from the last 10 years. These trades ended up winning an NBA Championship. The other trade would shape Canadian basketball forever.

The Toronto Raptors and the Six Biggest Trades in Franchise History

6 – Toronto Raptors Trade Terrence Ross for Serge Ibaka in 2017

In the last stretch of the NBA season, the Raptors were struggling to get wins. The Raptors then made a hard choice. They traded long-time Raptor Terrence Ross and a first-round pick to acquire the services of Serge Ibaka according to Mike Prada of SBNation.

He would average 14.2 points, 6.8 rebounds, 0.7 assists, 0.3 steals, and 1.4 blocks per game in the 2016-17 NBA season. This was good enough for the Raptors to get third place in the Eastern Conference. A position that may not have been possible if the Raptors did not get Ibaka. They would end up getting swept that year by the Cleveland Cavaliers in the Eastern Conference Semifinals.

Ibaka would have a disappointing 2017-18 season but bounced back in 2018-19. In that season, he averaged 15 points, 8.1 rebounds, 1.3 assists, 0.4 steals, and 1.4 blocks per game. He would improve on that in 2019-20. There he averaged 16 points, 8.3 rebounds, 1.5 assists, 0.5 steals, and 0.8 blocks per game.

He also stepped up in the NBA Playoffs. For example, in Game 3 of the NBA Finals against the Golden State Warriors, Ibaka made history.

5 – Toronto Raptors Trade Fan-Favorite Jonas Valanciunas for Marc Gasol in 2019

Jonas Valanciunas was one of the Raptors’ best players. He was drafted fifth overall in the 2011 NBA Draft. Valanciunas played for the organization from 2012-19. According to Alec Nation of Bleacher Report, the Raptors gave up Valanciunas, Delon Wright, C.J. Miles, and a 2024 second-round pick to the Memphis Grizzlies. In exchange, the Raptors acquired Marc Gasol.

Gasol played an instrumental role in the Raptors winning the NBA Championship. According to Owen Phillips of FiveThirtyEight, Joel Embiid was held to 21 points per 100 possessions in the NBA playoffs against the Toronto Raptors. This is much lower than Embiid’s season average in the 2018-19 NBA season for the Philadelphia 76ers. In that season he averaged 37 points per 100 possessions. This even continued to the NBA 2019-20 regular season, where Embiid scored 0 points on eleven attempts against Gasol.

Then in the Eastern Conference Finals, Gasol, along with the Raptors star player Kawhi Leonard, was tasked with guarding Giannis Antetokounmpo of the Milwaukee Bucks. This is what Antetokounmpo said according to Bruno Manrique of ClutchPoints:

“Now, every day in my head, I’m seeing Gasol double-team me,” Antetokounmpo said. “You think I’m joking, but I’m not. I’m not seeing anybody else. I don’t care who’s guarding me. Give me a name. Thaddeus Young. All I’m seeing is Kawhi, Gasol coming because I know that. When I get to that situation, it might not be them.”

4 – Toronto Raptors Trade Antawn Jamison for Vince Carter on 1998 NBA Draft Night

How the Trade Happened

Glen Grunwald, who was then general manager of the Toronto Raptors at the time, made one of the biggest trades in Raptors history. However, what made this trade so interesting was the way it was done according to Brian Boake of Raptors Rupture.

The Raptors, in reality, believed that Vince Carter was the best player in the 1998 NBA Draft. However, that was not the universal opinion of everyone on draft night. The Golden State Warriors, for example, wanted Antawn Jamison. The Warriors had the fifth pick and were scared the Raptors would take him a pick ahead of them at number four. This is the main reason why the Warriors approached the Raptors organization. The owners of both the Warriors and the Raptors (Larry Tanenbaum) made the deal official through a phone call.

Luckily for both the Raptors and Warriors, no one drafted either Carter or Jamison in the first three picks. The Raptors picked Jamison fourth while the Warriors picked Carter fifth. They then swapped players. The Raptors, in addition, would get “standstill” money from the Golden State Warriors.

Significance of Vince Carter

Carter played with the Toronto Raptors from 1998-04, making it to the NBA All-Star Game five times. He was the Raptors first-ever NBA All-Star in the 1999-00 season. In that season he averaged 25.7 points, 5.8 rebounds, 3.9 assists, 1.3 steals, and 1.1 blocks per game. He followed that up with a career year in the 2000-01 NBA season. He averaged 27.6 points, 5.5 rebounds, 3.9 assists, 1.5 steals, and 1.1 blocks per game.

However, his biggest impact was probably off-court. Tristan Thompson of the Cleveland Cavaliers said this according to Danielle Cadet of The Undefeated.

“Vince was our Michael Jordan,” he said.

When Carter was acquired by the Toronto Raptors, there were only three Canadian NBA players. They were Bill Wennington, Rick Fox, and Steve Nash. A fourth one would come in 1999. A player named Todd MacCulloch was drafted 47th by the Philadelphia 76ers in the 1999 NBA Draft, becoming the fourth active NBA Canadian player at the time.

However, this number increased four-times by 2019 NBA Opening Day. According to the Canadian Press of Sportsnet, 16 Canadian players were on opening day rosters. This is the second-most players of any nationality, only behind the US.

Carter played a big role in that. Now, there are several Canadians playing in the NBA. This trend will continue in the 2020s as the rise of basketball in the Greater Montreal Area is also taking place.

3 – Toronto Raptors Trade Fan-Favorite DeMar DeRozan for Kawhi Leonard in 2018

DeMar DeRozan’s Legacy in Toronto

This is probably the most famous trade to make the list. One of the Raptors’ all-time greats DeMar DeRozan, Jakob Poeltl, and a first-round pick was traded for Leonard, and Danny Green, according to Adrian Wojnarowski, a senior NBA insider of ESPN. There was a lot of talk about this trade. DeRozan, like Valanciunas, played for the Toronto Raptors for the entirety of their careers before getting traded.

Furthermore, DeRozan made it to the NBA All-Star Game four times as a Toronto Raptor and was considered the best Raptors player of all-time before getting traded. He was with the organization for the good and the bad times. From 2009-13, the Raptors failed to qualify for the NBA Playoffs. He then with Kyle Lowry led the team to six-straight NBA Playoff appearances.

This includes a first-ever Eastern Conference appearance for the Toronto Raptors in 2016. No matter what people say, DeRozan led the team to the Eastern Conference Finals and two Eastern Conference Semifinals. Chris Bosh was never able to accomplish that with the Raptors, and Carter only took the Toronto Raptors to the Eastern Conference Semifinals once in 2001.

Reasons for the Trade

Kawhi Leonard

However, the Raptors most notably came up short in the NBA Playoffs. This is especially true in 2015 where they were swept by the Washington Wizards and 2017 and 2018 where they were swept by the Cleveland Cavaliers and LeBron James.

The Raptors then decided to go all-in. Leonard, who won the 2014 NBA Finals MVP trophy, was their main piece. It has already been mentioned in this article how he and Gasol guarded Antetokounmpo, which showed his defensive prowess. However, he is also well-known for his offensive game. Most notably, his playoff series against the Philadelphia 76ers, where he scored over 30 points in five of the seven games.

This included scoring 45 points in Game 1 and 41 points in Game 7. The points in Game 7 included the game-winning shot that allowed the Raptors to advance to their second-ever Eastern Conference Finals appearance.

He represented the Toronto Raptors as a starter in the 2019 NBA All-Star Game. Leonard averaged 20.6 points, 9.8 rebounds, and 4.2 assists per game in the NBA Finals. This was good enough to win NBA Finals MVP as the Raptors captured their first-ever NBA Championship in six games against the Golden State Warriors.

Danny Green

The second player received from the NBA trade; Green also made an important impact with the Toronto Raptors. In the 2018-19 NBA season, he had a three-point shooting percentage of 45.5 percent. This is the highest shooting percentage in his career. He also performed well in the NBA playoffs. For example, in Game 3 of the NBA Finals against the Golden State Warriors. In that game, he scored 18 points, grabbed five rebounds, dished out one assist, had one steal, and he had one block.

2 – Toronto Raptors and Sacramento Kings Make Massive Trade in 2013

Before the trade transaction happened, the Toronto Raptors had a record of 6-12. Masai Ujiri thought his team needed a change, and the trade was made. According to Christopher Walder of Bleacher Report, Rudy Gay along with Quincy Acy and Aaron Gray were traded to the Sacramento Kings. In exchange, the Toronto Raptors received Greivis Vásquez, Patrick Patterson, John Salmons, and Chuck Hayes.

The Raptors finished with a record of 48-34 in the 2013-14 NBA season and made their first NBA playoff appearance since 2008. The Raptors went 42-22 for the rest of the season. They would lose to the Brooklyn Nets in seven games.

The Raptors, however, would never look back and qualify for the NBA playoffs seven straight times afterward. This includes booking a spot in the 2020 NBA playoffs before the NBA season was suspended because of the coronavirus pandemic.

This trade also allowed the Toronto Raptors to obtain Norman Powell according to Fox Sports. In the 2015 NBA Draft, the Toronto Raptors traded Vasquez. The Raptors in return received Powell and a 2017 NBA first-round pick.

1 – Toronto Raptors Acquires Kyle Lowry from the Houston Rockets in 2012

This is a very underrated trade made by then-president and general manager Bryan Colangelo, which did not get the hype or attention that the previous two trades on this list got. Lowry, who would become the face of the franchise was traded to the Toronto Raptors. In exchange, the Houston Rockets got a protected first-round pick from the Toronto Raptors according to Jonathan Feigen of Chron.

The Raptors were disappointed at the time as they failed to acquire Steve Nash in free agency. He would wind up with Kobe Bryant and the Los Angeles Lakers. Furthermore, Lowry came to Toronto as back up to Jose Calderon at the time.

However, Calderon was traded a year after to the Detroit Pistons in a three-team trade according to This gave Lowry the keys to the starting point guard position he always craved. He would then make the NBA All-Star Game six straight years in a row and played a pivotal role in the Raptors playoff and championship run.

He is now the current longest-tenured Raptors player. Lowry has had some big performances in the NBA Playoffs. In the 2016 Eastern Conference Semifinals, he finished with 33 points, two rebounds, and one assist in a tight four-point win over the Miami Heat. He would also have a big Game 7 with 35 points, nine assists, and four rebounds.

This win clinched the Toronto Raptors’ first-ever NBA Eastern Conference appearance. Finally, in 2019, Lowry had 26 points, 10 assists, and seven rebounds in Game 6 of the NBA Finals against the Warriors. This proved vital as the Raptors won their first-ever NBA Championship.

Overview of the Top Six Trades in Toronto Raptors History

Four of the six trades on this list came from Masai Ujiri and Bobby Webster. They are the current president and general manager of the Toronto Raptors. This is because of the success the Raptors have experienced since 2014. They have experienced much more success than previous Toronto Raptors teams, which only made it past the first round once before 2016.

However, this is not to say that general managers or presidents like Bryan Colangelo and Glen Grunwald did not contribute to the Raptors eventual success. Carter is the main reason why so many Canadians are playing in the NBA and Lowry has established himself as the greatest Toronto Raptors player of all-time. Both players made it to the top five players in franchise history. Without these two players, the Raptors’ history would not be complete.

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