Top 15 Worst Management Mistakes In Toronto Raptors History

Much like the Toronto Maple Leafs over the past 20 years, the Toronto Raptors franchise has struggled mightily. The method of this slump is a little different than that of the Leafs and has focused around terrible draft picks and not being able to keep their stars in Toronto.

Also the expectation of the Raptors is also a lot less than with the Leafs but with the recent hiring of Masai Ujiri, he has brought a new optimism to the team and the entire city has grown behind his moves. Success has followed his hiring but in the past the Raptors have been known to hire management that simply did not know what they were doing and this list is scattered with moves that will make you scratch your head.

The Raptors are clearly headed in the right direction and are a perennial Eastern Conference contender, but they still have only won one playoff round in their 20-plus year history. Until they have success in the playoffs the moves that put this franchise in the position that it is in will continue to haunt them.

I am confident as a Toronto Raptors fan that this team will have playoff success in the near future and is perhaps the team in Toronto that is built the best to maintain some sort of consistency with their current management and roster. Let’s hope so because the city of Toronto most definitely deserves a championship team and the Raptors just might be the team to provide it.

Continue scrolling to keep reading

Click the button below to start this article in quick view

Start Now

15 Trading Damon Stoudamire for Kenny Anderson

via hoopsaddict.com

In 1998 Glen Grunwald traded the first draft pick in Toronto Raptor history Damon Stoudamire for a guy that voiced his displeasure of playing in Canada and as such Kenny Anderson never played a game for the Raptors. Anderson was then in turn traded to the Boston Celtics for Chauncey Billups which was a great trade but the Raptors would not witness the great player and winner that Billups became because of a terrible misjudge in talent by Grunwald. Anderson was a solid NBA point guard but not someone that should have traded for an icon such as Stoudamire.

14 Drafting Terrence Ross

Tom Szczerbowski-USA TODAY Sports

There is nothing wrong with Terrence Ross as a player other than that he is a tease of a talent. Very athletic and able to hit the three pointer on top of being a versatile defender, Ross just has never been able to put all of his abilities together and be an NBA starter. His best game was on January 25, 2014 when he scored a staggering 51 points including 10 three-pointers but sadly Ross’s best statistical season was only shadow of this standout performance when he averaged 10.9 points during that same season.

13 Drafting Jonas Valančiūnas

Tom Szczerbowski-USA TODAY Sports

Like Ross, Valanciunas is a good player but not a player that is worth a top five draft pick selection as he was in 2011. Valanciunas puts up solid numbers and has averaged close to a double-double in limited minutes in his career, but he is not a star player and continues not to play during crunch time in the fourth quarter of games. So why the Raptors invested their pick and even were willing to wait a year before he played in North America is beyond me. The likes of Klay Thompson, Kahwi Leonard and Jimmy Butler, who are all All-Star talents were available after Valanciunas.

12 Tracy McGrady Exodus

via complex.com

I understand that in sports, when athletes become free agents they are free to sign wherever they want, but I would like to imagine what could have been if McGrady had decided to stay in Toronto after the 2000 season. Vince Carter and McGrady were best friends and everything was looking towards building a long-lasting relationship with the Toronto Raptors. Sadly, all that went astray and McGrady decided to go back home and sign with the Orlando Magic. It makes you wonder if the Raptors could have or should have done more to keep McGrady.

11 Drafting Michael Bradley

via windsorstar.com

Michael Bradley is the first in a list of painstakingly awful draft picks by the Raptors. His NBA career lasted only 173 games and he averaged an embarrassing 2.8 points per game. He was selected with the 17th overall pick in 2001 and never started more than 11 games in a single season which he did for the Raptors in 2003. All Stars Zach Randolph and Tony Parker were selected after Bradley.

10 Drafting Rafael Araújo

via nba.com

Araujo epitomized what was wrong with the Raptors in the mid 2000s. His career numbers were awful averaging a similar 2.8 points per game as Bradley but what makes Araujo stand out was that he clearly was not an NBA player and he looked lost on the court most of the time. How any organization could draft such an obvious non talent in the first round when players such as Andre Iguodola, Josh Smith and Al Jefferson were still available is beyond me!

9 Firing Sam Mitchell

Sam Sharpe-USA TODAY Sports

Mitchell was hired as the team’s coach in 2004 and won the coach of the year during the 2006-07 season. He is the franchises all-time leader in wins and also led the team to its first division title during the 2006-07 season. Regardless, Mitchell was fired at the start of the 2008-09 season after the Raptors started the year 8-9. There is no rational reason why management pulled the trigger on Mitchell so quickly and the Raptors went 25-40 the rest of the season. Mitchell’s successor Jay Triano lasted three years and only won 87 games.

8 Marcus Camby Trade

via thestar.com

Marcus Camby is the only player that is on this list twice. During the 1998 season he was traded to the New York Knicks for Charles Oakley. Oakley was a great Raptor and was a key to their playoff success when the team won their first round in franchise history, but Camby went on to be one of the best defensive players of his era. Camby won the NBA Defensive Player of the Year in 2007 and led the league in blocks per game on 4 different occasions. He also averaged 10 rebounds per game in his 19 year NBA career.

7 Drafting Alex Radojevic

via triangleoffense.com

There are terrible draft picks and there is Alex Radojevic. Radojevic’s time in the NBA was so plagued with injuries and disappointment that one can not even justify him having an NBA career. He played only 3 games for the Raptors during the 1999-00 season and managed only 3 points per game. He was also on the roster of the Denver Nuggets and Milwaukee Bucks but did not play a single game for them. The 1999 draft was not loaded with talent and Andrei Kirilenko is the only big name that was drafted. Regardless, Radojevic was picked 17th that year and was not even worth of that mid-first round selection with his lack of playing time in the NBA.

6 Firing Butch Carter

via torontosun.com

Butch Carter took on the coaching reigns of the Toronto Raptors during the 1997-98 season and in less than three years he changed the team from a perennial doormat in the NBA to a playoff team in 1999-00. However, Carter was fired in the same offseason by Glen Grunwald because of his problems with the media in Toronto and other irrelevant reasons. Butch Carter also had a great relationship with Vince Carter, a superstar in the NBA at the time and there is without a shadow of a doubt that Vince stopped caring and playing basketball in Toronto because Butch Carter was no longer there.

5 Drafting Andrea Bargnani

via wetalksports.sportsblog.com

Bargnani did not have a bad career with the Toronto Raptors and averaged close to 15 points per game including a career high 21.4 during the 2010-11 season. The reason why he is on this list is because of where his career is at now and that he was first overall pick in the 2006 NBA Draft. Since being traded to the New York Knicks in 2013 Bargnani has had an injury riddled career and not played in more than 42 games. He is now hanging onto his NBA life and all bets are that he is out of the league very soon.

His selection in 2006 becomes more painful to Raptors fans because with the second selection of that draft the Portland Trailblazers took LaMarcus Aldridge who is an NBA All Star and exactly what the Raptors have been and are currently still looking for.

4 Trading Chauncey Billips

via pinterest.com

Chauncey Billips is as high as he is on this list because he became an NBA Finals MVP and one of the clutch performers of his generation. He was traded at the end of the 1997-98 trade deadline for next to nothing other than Jonathan Bender who in turn was traded for Antonio Davis who became a nice piece with the Raptors. Billups would go on to help the 2003-04 Pistons win an NBA championship.

3 Drafting Marcus Camby

via raptorsrepublic.com

Somehow, Camby makes it on this list twice. While trading him was the wrong move, the big mistake was really back in 1996. The 1996 NBA Draft was filled with a host of future NBA hall of famers and unfortunately for the Raptors, Camby will most likely not be one of them. As already mentioned Camby had a really nice NBA career but NBA superstars such as Kobe Bryant, Ray Allen and Steve Nash were still available after Camby was selected with the 2nd overall pick.

2 Hiring Rob Babcock

via thestar.com

Babock may not be responsible for the most moves on this list but be is infamous for making the worst move in Raptors history which will be talked about in the number one entry. A couple of the other terrible moves by Babcock include signing Rafer Alston and drafting Joey Graham in the first round, but the trading of a Toronto icon for a bunch of spare parts is why hiring Rob Babcock is the second worst move in Raptors history.

1 Vince Carter Trade

via sportsnet.ca

Acquiring Vince Carter in a draft day trade in 1998 was the best move in Raptors history and subsequently when Rob Babcock traded Carter to the New Jersey Nets in 2004 for a diminishing Alonzo Mourning, Erik Williams, Aaron Williams and a pair of first-round picks which amounted to nothing, the franchise took a major hit. Reasons for Carter being traded circle around him not liking the hiring of Rob Babock from the get go and in today’s sports market you need to keep your superstars happy. Carter put Toronto on the basketball map and part of the success the Raptors are experiencing now are largely due to what Carter brought not to only Toronto, but the entire country of Canada as well.

Vinsanity was alive and well during his time here from 1998-2004 and he also revitalized the NBA witch his eye-popping performance during the 2000 NBA Slam Dunk Contest. That it went from this extreme high to him vowing to never dunk again at the end of his Toronto Raptor career is highly unfortunate. Carter may have been an immature player during his time in Toronto, but as a NBA veteran now he knows what he owes the city of Toronto a lot and I hope sometime in the near future Raptors management gives a worthy tribute to Vincent Lamar Carter because he truly deserves one.

More in NBA