Charles Oakley

The Ultimate Raptors Rankings are the RaptorBlog editors’ attempt to rank the top 30 Toronto Raptors of all time. These rankings are obviously somewhat arbitrary and endlessly debatable, but they’re based on each player’s contribution, performance and longevity as a Raptor, and on how beloved they are by Raptors fans. We’ll count down a new Raptor every Wednesday on this blog.

Charles Oakley’s Raptors résumé:

  • 113-95 (.543) record in 208 starts as a Toronto Raptor
  • 30 double-doubles and one triple-double (10 points, 11 rebounds, 12 assists)
  • Sixth in franchise history, rebounds (1,655)

There are two players that I feel deserve to be called “icons” in the 16-season history of the Toronto Raptors franchise. I don’t need to tell you who the first one is. The second one is Charles Oakley.

Oakley joined the Raptors in June 1998 when the Knicks traded him, Sean Marks and $8 million in cash (!) for Marcus Camby. Raptors GM Glen Grunwald wanted Oakley to bring toughness, veteran leadership and playoff experience to a team coming off a dismal 16-66 season. One can surmise that Grunwald hoped that Oakley would be a positive influence on the team’s two promising young prospects, Vince Carter and Tracy McGrady.

As we know now, Carter and McGrady are not among the best self-motivators in the NBA, so Grunwald’s instincts were dead on with Oakley’s acquisition. The combination of young athleticism and gritty veteran experience Grunwald put together resulted in the Raptors improving to 23-27 in the strike-shortened 1998-99 season, followed by back-to-back winning seasons and the franchise’s only playoff series win in 2001.

Oakley brought more than just a winning attitude to the team, he was the main reason the Raptors were a squad that was legitimately intimidating in spite of their purple uniforms. You’d be hard-pressed to find a more menacing and ripped frontcourt rotation than Toronto’s trio of Oakley, Antonio Davis and Kevin Willis in the 1999-2000 and 2000-2001 seasons.

Raptors fans love to hold up Oakley as an example of the kind of player this team is sorely lacking these days, and they’re not mistaken. But there’s a downside to having Charles Oakley on your team — he really doesn’t give a shit. I don’t mean that in the “he didn’t give 100 percent effort” way, but in the “he’ll say and do whatever he wants, whenever he wants, without caring about the potential consequences” way. That leads to some entertaining situations of course — such as the time he threw a basketball in Tyrone Hill’s face over a gambling debt and the time he punched Jeff McInnis before a game because Oakley had recently called the house of a woman he was dating and McInnis answered the phone — but that kind of behavior isn’t exactly conducive to winning.

Aside from his pregame altercations, Oakley secured his ticket out of Toronto during the Raptors’ 2001 playoff run by constantly insulting Vince Carter and bickering with Vince’s mother. Oakley was less than heartbroken about being traded to Chicago in the 2001 off-season, and he later said that Canadian basketball fans “don’t know polo from lolo”. I still don’t know what that means, but I would guess that it was not factually inaccurate.

Charles Oakley will always hold a special place in the hearts of Raptors fans, and some local media hacks will tell you that it’s because he brought a “hockey mentality” to the Raptors and Canadian sports fans appreciate that sort of thing. You know who else appreciated Oakley’s toughness? Bulls fans from 1985 to 1988 and Knicks fans from 1988 to 1998. What sports fan doesn’t enjoy having a badass like Oak on his team?

The Oak-man isn’t ranked 12th on this list because he was one of the more skilled players in franchise history. He’s ranked this high because if you polled Raptors fans and measured the approval rating of all the players in this ranking, I guarantee you that Oakley would rate the highest. Why? Because he’s a bad mother… shut your mouth!