Toronto Raptors: 5 Best/Worst Trades In Team History

The Toronto Raptors have been very active in the trade market since joining the NBA for the 1995-96 season. The team has only made five playoff appearances in 18 years, but there have been many attempts to shake up the roster in hopes of becoming a perennial contender.Toronto Raptors

There were many trades to sort through, however I was able to narrow down my top five best and worst deals in team history.


5. The Raptors trade David Andersen, Marcus Banks and Jarrett Jack to the New Orleans Hornets for Jerryd Bayless and Peja Stojakovic, Nov. 20, 2010.

In July 2009, the Raptors signed Jack to a four-year, $20 million offer sheet that was not matched by the Indiana Pacers. The deal reunited Jack, who had averaged 13.1 points in the 2008-09 season–at the time a career high–with former college teammate Chris Bosh and gave the Raptors an up-tempo point guard to contrast the steady hand of starter Jose Calderon.

Jack provided the offensive spark that was expected, averaging 11.4 points and five assists in 27.4 minutes per game while appearing in all 82 contests for the Raptors in the 2009-10 season.

Jarrett Jack

Jarrett Jack is averaging 17.1 points per game in the 2013 NBA Playoffs (

However, the move ignited a point guard controversy, a common theme in Raptorland over the years, with Jack making 43 starts to Calderon’s 39. Furthermore, it turned out to be the last season in Toronto for Bosh, the face of the franchise at the time.

Bayless possessed a skill set similar to Jack and appeared in 91 games for the Raptors over two seasons. In the summer of 2012, the Raptors chose not to retain the right to match offers for Bayless and he signed with the Memphis Grizzlies, where he is now contributing on a playoff team.

Andersen and Banks were not significant pieces in the deal that also brought in Stojakovic, who was hampered by injuries and only appeared in two games for the Raptors before he was waived two months after the trade.

These days, Jack is playing a significant role for the Golden State Warriors and finished third in voting for the Sixth Man Award behind Jamal Crawford and winner J.R. Smith in 2012-13.

4. The Raptors trade Maceo Baston, T.J. Ford, Roy Hibbert and Rasho Nesterovic to the Pacers for Nathan Jawai and Jermaine O’Neal, July 9, 2008.

This trade was a classic example of general manager Bryan Colangelo going for a home run that ends up as a swing-and-miss.

The idea was that the front-court tandem of O’Neal and Bosh would be a nightmare at both ends of the floor for opposing teams, but it turned out to be an awkward pairing and one that did not ultimately convince Bosh that the franchise was going to surround him with enough talent to compete for a championship.

Ford’s durability had been called into question because of various back and neck injuries and the Raptors again felt more comfortable moving forward with Calderon, but the name that sticks out like a sore thumb in this deal is Hibbert.

How the Raptors could not see that the 7’2″ Hibbert would have been a perfect fit for the team is anyone’s guess.

The O’Neal experiment did not even last an entire season as he was shipped to the Miami Heat for Shawn Marion in February of the 2008-09 season.

3. The Raptors trade cash to the Orlando Magic; the Raptors trade a 2016 second-round pick to the Memphis Grizzlies; the Raptors traded Kris Humphries, Nathan Jawai and Shawn Marion to the Dallas Mavericks; the Mavericks trade Jerry Stackhouse and cash to the Grizzlies; the Mavericks trade cash to the Magic; the Mavericks trade Devean George and Antoine Wright to the Raptors; the Grizzlies trade Greg Buckner to the Mavericks; and the Magic trade Hedo Turkoglu to the Raptors, July 9, 2009.

This massive four-team trade represents the lengths that Colangelo went to for the purposes of acquiring Turkoglu, whose value was in a state of euphoria after the Magic made a run to the NBA Finals in 2009.

The sign-and-trade arrangement that landed the versatile 6’10” forward in Toronto carried a price tag of five years and $52.8 million–money not well spent by the Raptors.

Turkoglu, who often appeared disinterested, lazy and became notorious for appearing in a local pizza commercial, was not the missing link for a team that still featured Bosh and Andrea Bargnani. Despite finishing with a record of 40-42, the Raptors failed to make the playoffs in 2009-10, Turkoglu’s only season with the team.

I will, however, give Colangelo credit for fixing this mistake and somehow convincing the Phoenix Suns to take Turkoglu in exchange for Leandro Barbosa in July 2010.

2. The Raptors trade Carlos Rogers, Damon Stoudamire and Walt Williams to the Portland Trail Blazers for Kenny Anderson, Gary Trent, Alvin Williams, two 1998 first-round picks and a 1998 second-round pick, Feb. 13, 1998.

I’m not going to complain about what the Raptors received in return for Stoudamire–the 5’10” point guard known as “Mighty Mouse” and 1995-96 NBA Rookie of the Year. Alvin Williams became the centerpiece of this deal for Toronto and went on to appear in 417 regular season games and 18 playoff games over an eight-year span with the Raptors.

The problem was that the franchise player was essentially quitting on the team and demanding a trade because he was tired of losing. Years later, Stoudamire said he regretted the way he handled the trade, but the damage was done and so from very early on in the franchises’ existence, there was a perception that the team could not hold on to its star players.

1. The Raptors trade Vince Carter to the New Jersey Nets for Alonzo Mourning, Aaron Williams, Eric Williams and first-round draft picks in 2005 and 2006, Dec. 17, 2004.

Jason Kidd

Carter teamed up with Jason Kidd in New Jersey. (Photo Credit: Mark Runyon, Basketball Schedule)

Easily the worst trade in franchise history and the lasting legacy of former general manager Rob Babcock.

This trade was such a monumental moment for the Raptors that I can actually remember where I was when news of the trade broke.

Although it was no secret that his time in Toronto was winding down, there was still a belief that some talent could be yielded in return for Carter who, like Stoudamire before him, pouted his way out of town.

Mourning never reported to the team, which surprised no one, and Aaron and Eric Williams were, at best, fringe NBA players. The first-round picks looked good on paper, but they amounted to Joey Graham and Renaldo Balkman.

Jalen Rose, a Raptor at the time, summed it up perfectly when he implied, sarcastically, that the team must have received Richard Jefferson in return, but unfortunately that was not the case.


5. The Raptors trade Charlie Villanueva and cash to the Milwaukee Bucks for T.J. Ford, June 30, 2006.

In a somewhat surprising move, Villanueva was dealt after averaging 13 points and 6.4 rebounds per game in his rookie season with the Raptors. However, Bosh was already cemented as the the starting power forward and Bargnani had just been drafted first overall.

The move paid off for the team as Ford averaged 14 points and dished out 7.9 assists in 2006-07 and the Raptors captured the Atlantic Division title by winning a franchise-high 47 games.

4. The Raptors trade Jose Calderon, Ed Davis and a future second-round pick to the Grizzlies; the Detroit Pistons trade Austin Daye and Tayshaun Prince to the Grizzlies; the Grizzlies trade Calderon to the Pistons; and the Grizzlies trade Rudy Gay and Hamed Haddadi to the Raptors, Jan. 30, 2013.

Calderon, a pending free agent, and Davis, a third-year forward whose value was at an all-time high, were packaged in a trade which finally brought the team a franchise-quality player that was lacking since the departure of Bosh.

Rudy Gay

The Raptors chances of success now rest on the shoulders of Rudy Gay. (Photo Credit: Keith Allison,

After starting the 2012-13 season 4-19, the raptors went 30-29 the rest of the way, finishing just four games back of the eighth-seeded Milwaukee Bucks.

The core group of Gay, DeMar DeRozan, Kyle Lowry, Jonas Valanciunas, and Amir Johnson should be able to end a five-year playoff drought for the Raptors next season.

This may end up being the last significant move for Colangelo because it has not yet been confirmed by the organization if he will return as general manager in 2013-14, a role he has held since February 2006.

3. The Raptors trade Marcus Camby to the New York Knicks for Sean Marks, Charles Oakley and cash, June 25, 1998.

The franchise gave up on Camby very early. He played just two seasons with the Raptors after they selected him second overall in the 1996 draft, but the team was in need of veteran leadership and toughness to complement a young nucleus that included Tracy McGrady and Vince Carter.

Even though Camby went on to have a successful career as a rebounder and shot blocker, the trade was beneficial to both teams. The Knicks advanced to the NBA Finals in 1999 and Oakley has received credit for motivating Carter during the team’s glory years (1998-2002), as crazy as that may sound.

2. The Raptors trade Jonathan Bender to the Pacers for Antonio Davis, Aug. 1, 1999.

Bender was drafted in 1999 by the Raptors and traded before he ever played a game for the team. While fans were intrigued by Bender, a 6’11” forward who made the jump from high school, not many complained when he was sent to the Pacers for Davis, an established NBA forward.

Davis’ time in Toronto did end on a sour note; however, he performed very well during his four full seasons as the team’s center.

1999-00 TOR 79 31.4 8.8 1.3 11.5
2000-01 TOR 78 35.0 10.1 1.9 13.7
2001-02 TOR 77 38.7 9.6 1.1 14.5
2002-03 TOR 53 35.7 8.2 1.2 13.9
Provided by View Original Table
Generated 5/14/2013.

Davis even earned a trip to the 2001 NBA All-Star Game.

1. The Raptors trade Antawn Jamison to the Golden State Warriors for Vince Carter and cash, June 24, 1998.

All along the Raptors wanted Carter, but they saved a little bit of money by selecting Jamison with the fourth pick in the 1998 draft and then trading him on draft day for Carter, who the Warriors had chosen with the fifth pick.

Jamison may have actually had the higher profile of the two University of North Carolina standouts, but Carter quickly established himself as an elite player and was named NBA Rookie of the Year in 1999.

Yes, Carter is still booed every time he touches the ball when he visits the Air Canada Centre as an opposing player, but there is no denying he put the Raptors on the map in the NBA and will always be associated with the early success of the franchise.

Tags: Jarrett Jack Nba Draft Nba Trade Deadline Raptors Trades Roy Hibbert Toronto Raptors Vince Carter

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