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5 Worst Free-Agent Signings in Toronto Raptors History

Christopher WalderContributor IIJanuary 10, 2017

5 Worst Free-Agent Signings in Toronto Raptors History

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    Money is the root of all evil. The Toronto Raptors know that all to well.

    For several years, this franchise has blatantly squandered their team bankroll in ways that just boggle the mind. Signing mediocre free agents to large contracts has been an all too common trend with the Raptors.

    There's plenty of blame to go around. On occasion, the newly signed player will fail to meet the lofty expectations set by their outrageous deal. 

    The opinion that past management had no clue how to spend their money wisely also exists, as well. Perhaps they saw something in said individual that simply wasn't there.

    The Raptors are constantly looking for that next big name on the open market to help put them over the top and back in the playoff hunt. 

    That has yet to occur. 

    Looking back at the history of this team and some of the more egregious signings they've made and heinous contracts they've handed out, it almost makes you want to cry.

    *No contract extensions or new deals for players who had been a part of the team the previous season were included in this list

    *sign-and-trade deals are allowed

    *All statistics/salary information provided by ESPN, Yahoo Sports! and HoopsHype. 

(Dis)Honorable Mentions

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    Rafer Alston, PG, 2004-05 (six years, $30 million)

    "Skip 2 My Lou." From a Streetball legend to a starting point guard in the NBA, Rafer Alston attempted to make the difficult transition as seamlessly as possible.

    In the end, Alston proved to be more flash than substance during his second go with the Raptors. Attitude problems and an apparent feud with the head coach sealed his fate with the team. 

     

    Fred Jones, SG, 2006-07 (three years, $11 million)

    An overrated shooting guard who struggled to create his own shot. Winning the 2004 NBA Slam Dunk Contest was his big claim to fame in the NBA. That's fine and all, but slamming the ball through the basket only matters if you can find ways to get to the net. The Raptors learned the hard way that Jones was incapable of making that happen.

    After just 39 games with the team, Jones would be dealt to the Portland Trail Blazers for guard Juan Dixon. 

     

    Michael "Yogi" Stewart, PF, 1998-2002 (six years, $24 million)

    This was a tough call to make. On one hand, Michael Stewart's insane contract could easily put him as one of the two or three worst deals in team history. On the other hand, Stewart had received a one-year, $1 million contract from the team in his second year in the league. A longer, more handsome sum of a deal was promised to him for the following season.

    At the very least, he's worth mentioning on this list, not only because of the money he cashed in on, but for his distinction of being one of the lousiest players to ever suit up for this team. The most points he ever averaged in a Raptors uniform was 2.0.

    That says it all. 

5) Linas Kleiza, SF, 2010

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    Contract: four years, $20 million

    Tenure with Raptors: 2010-present

    2010-11 statistics (best season): 39 games played, 26.5 minutes, 11.2 points, 43.8 percent from the field, 4.5 rebounds, 1.0 assists, 0.5 steals, 0.2 blocks, 1.7 turnovers, 10.1 PER

    In three full seasons with the Toronto Raptors (includes the 2011-12 lockout season), Linas Kleiza has played in just 108 games, including 20 in 2012-13.

    Serious knee issues have put his career at a standstill. Kleiza hasn't been the same player since suffering a meniscus tear in his right knee in 2010-11, and after undergoing arthroscopic surgery in 2011. 

    His 33 percent shooting from the field this past season was the worst of his career, while his 7.4 points per game was his lowest scoring output since his rookie year.

    It's hard to pile on a player who's truly experiencing some bad luck with injuries, but the power of the almighty dollar rears its head once again. 

    Even if he were healthy, Kleiza is far too inconsistent and erratic to be making that kind of coin. He has stretches where he looks brilliant and well worth the money, but the bad has far outweighed the good. 

    Kleiza is set to make $4.6 million in 2013-14, unless the Raptors decide to amnesty him. 

    That's something they should strongly consider doing, if they haven't already. 

4) Jason Kapono, SF, 2007

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    Contract: four years, $24 million

    Tenure with Raptors: 2007-09

    2008-09 statistics (best season): 80 games played, 22.9 minutes, 8.2 points, 42.8 percent from three-point range, 2.0 rebounds, 1.3 assists, 0.3 steals, 0.0 blocks, 0.9 turnovers, 8.9 PER

    Jason Kapono is a sharpshooter from three-point range. His 43.7 shooting percentage from behind the arc ranks him fifth all-time in NBA history. 

    Other than his ability to shoot the basketball at a highly efficient rate, there isn't a lot more to Kapono's game.

    He's fairly one-dimensional to say the least. 

    Yet, despite his fairly limited skill set, the Raptors decided to throw caution to the wind and pay Kapono their entire mid-level exception early that offseason.

    The team needed players to space the floor, as to give All-Star Chris Bosh more options when working in the post. In that sense, Kapono was a perfect fit.

    Unfortunately, when it came to producing in other facets of the game, Kapono was a huge liability. 

    On June 9, 2009, Kapono was traded to the Philadelphia 76ers for forward Reggie Evans. 

3) Landry Fields, SF, 2012

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    Contract: three years, $19.5 million

    Tenure with Raptors: 2012-present 

    2012-13 statistics: 51 games played, 20.3 minutes, 4.7 points, 45.7 percent from the field, 4.1 rebounds, 1.2 assists, 0.6 steals, 0.2 blocks, 0.8 turnovers, 10.3 PER

    It seemed like an all-too-perfect plan.

    The Toronto Raptors were going to sign Landry Fields to an expensive offer sheet that the New York Knicks would consequently have to match. The Knicks didn't want to let Fields walk for nothing, so of course they were going to match any offer thrown his way.

    Right?

    Wrong. 

    During the 2012 offseason, the Raptors were primed and ready to make a strong push for two-time NBA MVP and Canadian hero Steve Nash. The Knicks would be theoretically taking themselves out of the Nash sweepstakes by matching the Raptors offer for Fields. 

    Well, the Knicks didn't match the offer, thus forcing the Raptors to acquire a talent who saw major drops in production from his rookie to sophomore year. 

    Fields' inaugural season in Toronto left a lot to be desired. He missed 31 games with an elbow injury that was triggering spasms in his shooting hand. 

    There's still plenty of time for Fields to one day play up to the money he's making, but as of now, his overly generous contract is looking rather dejecting to Raptors' fans. 

2) Hakeem Olajuwon, C, 2001

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    Contract: three years, $17.4 million (sign-and-trade)

    Tenure with Raptors: 2001-02

    2001-02 statistics: 61 games played, 22.6 minutes, 7.1 points, 46.4 percent from the field, 6.0 rebounds, 1.1 assists, 1.2 steals, 1.5 blocks, 1.6 turnovers, 14.4 PER

    Hakeem Olajuwon left "The Dream" in Houston. 

    From the moment he arrived in Toronto to the time he "left," Olajuwon was simply a nightmare.

    It's not entirely his fault, though. Olajuwon turned down a three-year, $13 million deal with the Houston Rockets, a team that he won two NBA Championships with, to take a larger deal ($17.4 million over three years) with the Raptors. 

    That would be quite a lot of money to turn down for a 38-year-old center nearing the end of his storied career.

    The Raptors bit. They truly believed that Olajuwon would be one of the final pieces to the puzzle in order to become championship contenders. 

    That never panned out.

    Olajuwon averaged career-lows in points (7.1) and rebounds (6.0) in Toronto. He retired after just one season with the team due to a back injury. His health issues would have been easily detected prior to signing him if the Raptors had been more thorough in their medical evaluations. 

    Despite not being an active member of the roster, the Raptors kept paying Olajuwon the remainder of his contract, which counted against the salary cap. 

    Olajuwon's No. 34 was retired on the night of a Raptors vs. Rockets game in Houston, Texas. Toronto was still paying him as his jersey was being hoisted to the rafters for another team.

1) Hedo Turkoglu, SF, 2009

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    Contract: five years, $53 million (sign-and-trade)

    Tenure with Raptors: 2009-2010

    2009-10 statistics: 74 games played, 30.7 minutes, 11.3 points, 40.9 percent from the field, 4.6 rebounds, 4.1 assists, 0.7 steals, 0.4 blocks, 1.7 turnovers, 13.3 PER

    Pizza

    Ball.

    In all fairness, it's hard to blame former GM Bryan Colangelo for acquiring Hedo Turkoglu.

    Was he worth $53 million over five years? Absolutely not.

    However, Turkoglu was coming off a successful playoff run the previous season, having averaged 17.5 points, 6.4 rebounds and 5.5 assists for the Orlando Magic.

    Colangelo was willing do whatever it took to convince Chris Bosh to re-sign with the team, rather than lose him in free agency in 2010 (which happened anyways).

    At the time, it looked like an excellent move. Even if he were overpaid, if Turkoglu's presence on the Raptors were to keep Bosh in the city, then it would all be worth it.

    How wrong they were.

    In Orlando, Turkoglu was able to be a facilitator with the basketball, despite playing small forward. His role changed drastically with the Raptors, as starting point guard Jose Calderon was the one who controlled the offense. 

    Turkoglu was unable to adapt and mesh with his new teammates. He became lazy, lethargic and basically half the player (perhaps less) he was with the Magic.

    At one point during the season, Turkoglu was benched and fined by the team for going clubbing after a loss to the Denver Nuggets, a game he didn't play in because of an apparent stomach virus. 

    On July 14, 2010, Turkoglu was traded to the Phoenix Suns for Leandro Barbosa and Dwayne Jones. 

    The madness was finally over. 

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