NBA Toronto Raptors

Toronto Raptors: 5 Worst Trades in Franchise History

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The Worst deals in Toronto Raptors' history

Tom Szczerbowski-USA TODAY Sports

In 1995, the NBA decided that it was time to expand into Canada. Despite the traditional difficulties associated with recruiting star players to expansion teams, the Toronto Raptors have actually seen their fair share of talent over the years. Quality role players, future champions, all-star players, and a couple of borderline future Hall of Famers have all once dawned the dino across their chest. Not bad for a franchise that's playing little brother to the Toronto Maple Leafs. So, what has the Raptors' franchise done in its 18 years of existence with its steady stream of talent?

Not much. Five total playoff appearances, one playoff series win and one Atlantic Division title in 2007.

With the likes of Chauncey Billups, Damon Stoudamire, Vince Carter, Antonio Davis, Tracy McGrady, Chris Bosh, Hakeem Olajuwon and Marcus Camby, along with a laundry list of other solid pros who eventually contributed to meaningful championship-caliber teams in the future, how is it then possible that the Raptors' franchise has been sputtering in mediocrity for the majority of its existence?

Well, in the Raptors case, sometimes it was simply bad timing. Raptor fans still vividly remember the infamous sibling rivalry that ensued between McGrady and Carter after McGrady signed with the Orlando Magic openly saying that his older cousin was taking away from his shine. Not much a franchise can do about that when a player is that egotistical and determined to get theirs. Similarly, die hard Raptor fans still probably remember when Stoudamire forced his way out of the Great White North claiming that the franchise wasn't committed to winning, only to then have the franchise trade for Carter on draft night a few years later. What could have been.

Then there's the other reasons for the Raptors run of mediocrity: the general managers. Not only have they made some bad moves, they've made some franchise-devastating moves that the Raptors felt for years after the fact.

Here's a closer look at the five worst trades made in franchise, all of which impacted the Raptors' franchise years after the fact.

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5. Jarrett Jack traded to the New Orleans Pelicans

Jarrett Jack
Evan Habeeb-USA TODAY Sports

When the Raptors acquired Jarrett Jack in the summer of 2009 they were in the "win now" mode as they also took on the hefty contract of Hedo Turkoglu in the hopes of a deep playoff run. Jack provided exactly what the dinos needed at the time: toughness, leadership and scoring. Averaging 11.4 ppg, and five apg in just 27.4 minutes of action that season, fans became enthralled with Jack's uptempo style and gutsy play, something they had not seen at the point guard spot since Alvin "Boogie" Williams. Jack also provided the perfect contrast to Jose Calderon's slow but surgical approach to the game as they proved to be a tough tandem for opponents to deal with that year.

At the time, GM Bryan Colangelo felt as though his hand was forced as he wanted to avoid another point guard controversy which had plagued the team just a few years back with T.J. Ford and the aforementioned Calderon. In the end, apparently, the best offer on the table for Jack was Jerryd Bayless and a broken down Peja Stokajovic. Stokajovic, mired in injuries at this point, appeared in just two games before he was waived. Bayless appeared in just 91 games for the Raptors over the next two seasons as Colangelo didn't match the Memphis Grizzlies offer sheet. Bayless walked in less than a year and half.

Surely for any Raptors fan, it must have been painful seeing Jack just a couple years later torching the 2012-13 playoff scene with the Golden State Warriors. He excelled, averaging 17.1 points per game off the bench while the Raptors continued to rebuild.

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4. Marcus Camby to the New York Knicks

Marcus Camby
Tom Szczerbowski-USA TODAY Sports

On June 25, 1998, the young Raptors traded their promising young center, Marcus Camby, to the New York Knicks in exchange for Charles Oakley, Sean Marks and cash. Raptor fans may be divided on this trade being at the four slot. On the one hand, Oakley certainly wasn't brought into the Raptors locker room for his statistically contributions to the team. Oakley clearly was on the tail end of his career when he headed to Toronto. He was brought in for the intangibles: leadership, toughness and for the mentoring and maturation process of the young Carter and McGrady duo. Oakley certainly did contribute to the Raptors in this regard. Yet, Raptor fans can't look past the accomplishments that Camby went on to string together during his 15-year NBA career. After leaving the Raptors, Camby would go on to become one of the better defensive players of his time. Camby was a four-time member of the NBA All-Defensive Team and recipient of the Defensive Player of the Year Award in the 2006-07 season. Camby regularly was the defensive anchor of his teams; evidenced by him sitting 12th all-time for career blocks and 39th all-time for total rebounds per game. Interestingly enough, the Raptors dealt Camby away in his second year in the league in which Camby swatted away an obscene 3.7 shots per game. In some instances, the intangibles outweigh the stats. In this instance, it didn't. Raptors lost this trade.

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3. T.J Ford, Roy Hibbert, and Rasho Nesterovic traded to the Indiana Pacers

Jermaine O'Neal
Kyle Terada-USA TODAY Sports

On July 9th, 2008, the Raptors traded Maceo Baston, T.J Ford, Roy Hibbert, and Rasho Nesterovic to the Indiana Pacers in exchange for Nathan Jawai and Jermaine O'Neal. Similar to the fifth spot, this trade ended up in the Raptors receiving essentially nothing in return when it was all said and done. Then general manager Colangelo traded away his starting point in Ford, along with the Raptors first-round selection of Hibbert for an aging O'Neal. The O'Neal-Bosh tandem never quite panned out as planned as O'Neal was plagued with injuries throughout the 2008-09 season. He would go on to average 13.5 ppg and 7.0 rpg -- respectable numbers. Yet, that couldn't have been the fearsome twin tower duo that Colangelo was speaking of when he dealt for O'Neal.

O'Neal would go on to be traded to the Miami Heat later that year for Shawn Marion who would have a cup of coffee with the Raptors for the remaining 27 games before signing with the Dallas Mavericks in the offseason. Yet, the worst part of this trade, hands down, has be that the 7-foot-2 center Hibbert was let go for O'Neal in the process. Hibbert would later blossom into one of the premier big men in the NBA and is currently an integral piece of the championship-ready Pacers. In summary, in trading for O'Neal, Colangelo got rid of his starting point (Ford), starting center (Nesterovic), a future All-Star center (Hibbert) and a whole lot of wins.

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2. Raptors trade for Hedo Turkoglu

Hedo Turkoglu
Jeff Griffith-USA TODAY Sports

Hedo Turkoglu landed in Toronto through a massive and complicated four team sign-and-trade scenario which involved the Raptors giving up Shawn Marion, Kris Humphries, Nathan Jawai, cash, and a 2016 second round draft. In return the Raptors received Turkoglu. Turkoglu signed to a five-year, $52.8 million deal; probably the worst contract agreed to in Raptor history. At first, when Turkoglu was sitting out practices and exhibition games because of "soreness" and "exhaustion" from the previous season and the World Championships, Raptor fans gave him the benefit of the doubt. After all, this was the same player who was the orchestrator of the Magic's unlikely Finals run in just the previous season. His season averages of 16.8 ppg, 5.3 rpg and 4.9 apg were exactly what the Raptors needed. Finally, a sidekick to Chris Bosh. All signs pointed toward the Raptors making a serious Finals run in that 2009-10 season.

As Turkoglu poured in mediocre performance after mediocre performance, Raptors fans started to figure it out. Turkoglu wasn't exhausted or sore, he was just fat and lazy. It was a classic example of a player having a great contract year and then resting on his laurels. Turkoglu had gotten his money and he didn't really care after that. The 2009-10 "Turk" season easily has to be one of the more disappointing seasons in the Raptors history as the team failed to even make the playoffs, collapsing down the home stretch of the regular season. For a near $10 million annual salary player, Turkoglu was awful in his lone season with the Raptors, averaging 11.3 ppg on 40.9 percent shooting before being traded to the Phoenix Suns in the offseason.

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1. Vince Carter traded to the Brooklyn Nets

Vince Carter
Jerome Miron-USA TODAY Sports

There's not much about this trade that hasn't already angrily been said amongst Raptor fans. In trading the cornerstone of the franchise, a perennial All-Star, a former slam dunk champion and a revolutionary of Canadian basketball, then general manager Rob Babcock received a lot of nothing in return. The Raptors received two journeymen players in Eric Williams and Aaron Williams (not related). Babcock would then turn the Brooklyn(then New Jersey) Nets' two first round draft picks into Joey Graham and Renaldo Balkman, two borderline NBA-caliber players. To top it off, the main attraction of the deal, Alonzo Mourning, refused to show up to Toronto and was quickly waived thereafter. The effects of this trade would be felt for years to follow. The Raptors were consistently bottom feeders following this deal and have never been able to recapture the Carter glory days, even to this day. The Carter deal is easily the worst trade in franchise history and maybe even takes the cake as the worst move in Raptors' history (although the Rafael Araujo draft pick was pretty bad too).