In a 19-year run as a no-nonsense, all-elbows NBA forward, former Raptor Charles Oakley occasionally likened his on-court role to that of a butler in a mansion: He did the dirty work.
“I’m just happy to clean up and make sure everything’s all right,” he once said.
Now that the retired butler is the author of an excellent new NBA memoir, “The Last Enforcer,” let’s just say he’s hardly averse to scattering a career’s worth of collected grime around the league’s palatial estate. As much as Oakley’s book charts his inspiring rise from the bleak streets of hometown Cleveland to a life rubbing shoulders with basketball royalty — no less than Michael Jordan venerates Oakley as “my enforcer” in the book’s foreword while fellow Ohioan LeBron James has called Oakley a “legend” — it also checks off a highly readable hit list of enemies past and present.
Ink is spilled on Oakley’s ongoing feud with New York Knicks owner James Dolan, not to mention the list of ex-Knicks who stayed quiet after Oakley was disgracefully removed from Madison Square Garden as he attempted to watch a game in 2017.
Oakley takes a comprehensive inventory of personal feuds that go back further, including blow-by-blow details of Toronto-based run-ins with Tyrone Hill (over money) and Jeff McInnis (over a woman). Raptor fans will appreciate the homage paid to the likes of one-time Raptor teammates Vince Carter and Tracy McGrady — whom Oakley insists would have rivalled Lakers duo Shaquille O’Neal and Kobe Bryant for basketball supremacy if they’d stayed together in Raptorland. Still, Oakley at times takes aim at Carter and former Raptors coach Lenny Wilkens for their various sins against the good of Canada’s NBA team.
“There’s a lot of love in this book. People showed me a lot of love in my career,” Oakley said in a recent interview. “And for those that didn’t show me love — I let ’em have it.”
Never holding back is nothing new for Oakley, who racked up fights and fines in quantity during his playing days. But as much as he’s best remembered as a bringer of NBA pain, sitting fourth on the all-time NBA personal fouls list, he’s also an accomplished maker of notable pals. He tells readers he’s old chums with Oscar-winning actress Halle Berry, who’s also from Cleveland. He writes that he knew James was taking his free-agent talents to South Beach long before even Pat Riley, the Miami Heat president, was wise to James’s landmark 2010 decision. And he relays an anecdote about Dolan refusing to shake his hand during a meeting at the 2014 all-star weekend that ends with James, again on the road to free agency, proclaiming: “This is why I’m never going to New York.”
It’s tough slogging for downtrodden Knick fans. But thanks to Oakley’s sense of humour and the deft touch of co-author Frank Isola, the long-time New York hoops reporter, even the grinding of axes is mostly delivered with a twinkle in the eye and a chuckle after the fact.
“It’s like they say: If you get shot and live, you ain’t dead. So be blessed,” said Oakley, providing some helpful perspective to the targets of his score settling. “It could be worse.”
It could be worse. Tell that to Patrick Ewing, Oakley’s New York teammate, whose failings as a player and a friend get a comprehensive dismantling.
“It did hurt when (Ewing) didn’t stand up for me with Dolan. You play with someone for 10 years, I had his back,” Oakley said. “(Ewing) always said, ‘I’d go to war for Oak.’ I mean, there was a war. He didn’t go.”
And tell that to Charles Barkley, the Hall of Fame player turned TNT analyst, who gets worked over perhaps more roughly than anyone not named Ewing and Wilkens (the latter of whom Oakley accuses of being “on vacation” as the Raptors attempted to chart their path through the Eastern Conference playoffs in 2001 and beyond). Along with setting the record straight on the long-told story of Oakley’s fight with Barkley at a late-1990s players’ association meeting — “I did not punch Charles Barkley,” Oakley clarifies in the book. “I did, however, slap the shit out of him” — Oakley refuted Barkley’s recent public claims that their relationship has since become cordial.
“He’s not close with Michael (Jordan) no more. I don’t know who he’s really on (good) terms with now,” Oakley said of Barkley. “So I know he wants to come to the cookout and play 18 holes with us. But we’re not inviting him no more. He’s out. You act up, you go stand in the corner with one leg in the air .... That’s Charles, in the corner of the playground by himself. You can see him, because he’s kind of big.”
Oakley’s philosophy on fighting is simple: “Someone starts it. I end it,” he writes. As for his career as a coach — he spent a year as an assistant coach in Charlotte, where Jordan owns the team, and some time in the Big Three league — Oakley acknowledges his blunt-force style wasn’t well-received.
“When I coached those couple of years everybody said, ‘Be easy on the guys.’ OK. My easy isn’t 60. My easy is 85. If you’re doing below that, (the players are) going to take advantage of you,” Oakley said. “It’s a players’ league. Players don’t like it, they call their agents, they don’t talk to the coach. They go straight to the GM. It’s just sloppy, the way owners and GMs let these guys do stuff. There’s too much control with the players.”
Never shy about airing his opinion on the state of the sport — Oakley has long been of the mind it’s in decline — he’s appalled by the current generation of load-managed entitlement.
“Guys are so sensitive. Like now in the game, everybody wants to talk to the officials ... You’ve got the 12th man talking, the ball boy talking, the cousin in the stands talking,” Oakley said. “There’s too much talking to the officials. I don’t know why the league allows it. Everybody complains. They’re flopping. It’s taking away from the game. And the game ain’t great as it is. It’s just crazy.”
Now 58, an age when plenty of his hardwood brethren show the signs of the NBA grind with pronounced limps and seizing joints, Oakley said he remains mostly free of such maladies.
“When I get up in the morning, I try to do 200 or 300 sit-ups and go to the gym four or five times a week. So I’m good,” he said. “I did a lot of diving on the floor, chasing balls, jumping in the stands. But God, he helped me through all of that.”
The lone exception are his aching toes.
“My toes are sore,” he said. “I went into the league wearing size 14 (shoes). I came out wearing 16. I might have to go to 17. Because I need my toes to breathe.”
You know what they say about guys with big feet: They’ve got big chips on their broad shoulders. Wrapping up a wide-ranging chat with the 416 area code, Oakley said his first book of score-settling might not be his last.
“I went easy on (Ewing). The next book I’m going all out,” Oakley vowed. “This is just the layup-line book. Wait ’til the game starts.”

Opinion | Charles Oakley tells all in new book on feud with Knicks owner James Dolan, time with Raptors
The 19-year NBA veteran checks off a highly readable hit list of enemies past and present in an excellent new memoir “The Last Enforcer.”