Charles Oakley is amazed at how far basketball in Toronto has come

One of the most telling anecdotes in Charles Oakley’s candid new memoir, The Last Enforcer, involves the 1993-1994 New York Knicks, popcorn, Pat Riley, and the Val Kilmer and Kurt Russell Western, Tombstone.

Oakley recalls a losing stretch in late-January of that season when the team, exhausted and with morale at a perceptible low, climbed wearily onto their bus one grey morning while on the road in Seattle. They were expecting to head right to practice — this was the team known for its physical dominance and all-consuming defence in an era where the Eastern Conference was stacked with hard-nosed competitors — but the bus made a detour and the team soon found themselves at a local movie theatre which Riley had readied for them, making sure plenty of popcorn, candy and soda were waiting.

It was a rare day off for that Knicks team — the same group that would go on to challenge Hakeem Olajuwon’s Houston Rockets for the Championship that season — as it was for Oakley, a dogged worker and consummate competitor, but the memory stands out because of how surprising it seems at the surface.

“If we lost our game, we’d be on court practicing the next day,” Oakley tells Yahoo Sports Canada over Zoom. “He kept us focused. He prepared you. He always had something prepared, no matter what. He had something positive for the team.

Dig deeper, as Oakley spends the bulk of this retrospective story doing, and the thoughtfulness underlying Riley’s decision to give his team a day off is a mirror example of the thoughtfulness in which Oakley attempts to live his life, on and off court.

“I don’t think I put this one in the book, but [Riley] used to bring us over to his house for a Christmas parties as a team,” Oakley recalls, “He tried to get that core group of guys to bond together, and that’s how you win, that’s how you build.”

“One thing I try to show in the book is that my life has been consistent on the floor and off the floor, with people especially,” he adds.

The Last Enforcer follows a loose chronology of memory from Oakley’s childhood, growing up the youngest of six children under the care of their single mom, the sharp and driven Corine, in Cleveland, and grandparents, Julius and Florence Moss, in York, Alabama. Oakley wasn’t close with his father, who he remembers in the book as a familiar presence in the neighbourhood more than in his immediate life, and who died of a heart attack at thirty-five when Oakley was nine. He credits his grandfather, and the years he spent away from Cleveland and his mom in the south, with giving him the perspective he’d adopt and apply to his life and his game — sacrifice, with a big side of compassion.

For all the laugh out loud (there’s a lot) and wild in-game moments Oakley recounts with his signature, very direct style, his moral compass is never in doubt. When Oakley got physical in games, it was because he saw it as his job to defend his teammates, and when Michael Jordan and Patrick Ewing were your teammates, there were a lot of guys coming for them. The rare occasions Oakley took umbrage off the court came when someone ignorantly stumbled over his straightforward approach to most altercations: if you’ve done something wrong, own it and apologize.

Oakley doesn’t leave out the bad in favour of the good. The book is full of re-lived close losses that still ring with the sound of 20,000 people’s held breaths collectively leaving their lungs, like they did over two decades ago in Madison Square Garden, as it is with bumpy relationships with former teammates and a critical eye turned on NBA front offices, and himself.

In an early chapter, Oakley recalls two incidents that raised ire with former Chicago coach Doug Collins, and were what he believes got him traded away from Jordan’s Bulls. First, recognizing that opponents put the most pressure on Jordan, he asked Collins to run some plays for him and his teammates, noting, “How are we going to score if there are no plays run for the rest of us?” After that, when the Bulls lost their Christmas Day game by one point to the Knicks, Collins stormed into the locker room fuming, reneging the promise he’d made to the team that guys could take a day off to head home for the holidays. Oakley, who notes he was fine being alone for the holidays, just didn’t think it was right to go back on a promise.

There would be similar instances with his coaches in New York and, when he was traded north to an expansion franchise fighting an uphill battle against hockey, Toronto. Oakley would offer valid insight from his position on the floor, whether it be running plays for big men or where he thought young stars, like Vince Carter and Tracy McGrady, could use some help, and be considered difficult. In that way Oakley was ahead of his time in player empowerment, his willingness to be a vocal leader, and edging toward the kind of positionless play now proliferating in the league.

Oakley has been critical of the modern NBA before, and while that perspective was certainly a driving force behind the book (look no further than the title), his judgements fall along the same clean lines as his principals. His criticisms aren’t cruel or for clicks as much as they are engaging with a game he understands has grown into something different.

“The game changes,” Oakley says, “The game went outside. Three pointers, a lot of pick and rolls. Not saying it pushed me out, but there was more of a younger spirit. They didn’t want veterans around. You gotta know when someone is trying to push you out the door.”

A point that Oakley comes back to in The Last Enforcer often is the willingness to do whatever it takes to win, whether through the physicality of his game or working to create a close-knit group off court. There are only a few of his contemporaries — Riley, Jordan, Olajuwon — Oakley assigns this winning character trait to, with most former, and current players falling short. But what does it actually entail, now or then, to win, especially when you’re losing?

“Learning to win is sacrifice,” Oakley stresses, “Sacrifice, knowing that your team needs you every night, knowing that when you’re in the game who you’re playing with and what his strengths and weaknesses are. It’s just a lot of details.”

He draws on a relevant comparison, “It’s like putting this book together. You’ve got 270 pages. We didn’t go from one to 270,” Oakley laughs, “it’s a lot of work. You’ve got to be mentally tough. Some guys can’t do it.”

With a player — and person — like Oakley, who’s been mythologized for so long, it can be a little jarring to realize that the parts of his career that seemed especially formidable, or foundational, were also so fleeting. In his book, Oakley recalls that when he finally arrived in Toronto after being delayed at the Canadian border he settled into his hotel room at the Royal York and tried to flip to ESPN, but only found hockey. His time as a Toronto Raptor spanned just three seasons, but impacted him and the popularity of basketball in the city deeply.

“It’s amazing,” Oakley says when asked if it feels surreal to see how huge basketball is in Toronto, or Canada at large, “When they won the championship, I came to three games up there. Once they got Kawhi Leonard, he was just like the lead singer in the Temptations. He just did so much. And that one shot from the corner, when the ball just,” he smiles, voice slowing, “bounce, bounce, bounce, bounce — that was all in god’s plan.”

The city is still close to his heart. Oakley compares the ubiquity of Raptors fandom to that of New York — “Everywhere I go, I see a Toronto Raptors fan” — and he sees bright flashes of that rare quality of his kind of toughness in the team.

“Kyle [Lowry] is a little bulldog,” Oakley chuckles, recalling a pickup game the two played in Vegas, “Kyle definitely could play back in our era because he’s cut like that. When he played with Toronto, he showed a lot of heart and courage.”

Oakley also credits the team’s current leader, Fred VanVleet, for his “mental toughness, desire, a lot of work and effort put in” and says he’s proud of him for making the All-Star team.

“He came in playing backup and now he’s the starting point guard. Him and Kyle were the one and two punch last year, now he’s making the All-Star team. That’s showing how much work he put in,” Oakley says of VanVleet, “I don’t think he’ll ever be sidetracked because he gets it. He built himself up to the point of where he is today and it goes to show you, he’s still working.”

Oakley is still working, too. A lot. He’s a passionate chef, he credits his grandmother and mom (“she’s not picky as me, but she’ll let me know if it ain’t right” ) for fostering that love in him. He’s host of a cooking show, cooks often for friends and charity events through his own Charles Oakley Foundation, and is working on a cookbook. He was a recent contestant on Dancing With The Stars, which he points out was another thing his mom loved “because they would sit around laughing at me,” but his reason for doing the show ran deeper.

"I’m not a great dancer, but the only reason I did that was because the last time I was on television, it was in Madison Square Gardens, and what happened was bad. So I said, you know what? Let me show people that I’m not scared to try things.”

The incident he’s referring to happened in 2017, when Oakley, in his seat courtside, was suddenly swarmed by security at a charity event at Madison Square Garden and forcibly removed from the building at the puzzling and abrupt behest of Knicks owner, James Dolan. Dolan put out several hasty statements in an attempt to explain, and then reconcile, but the damage was done. Oakley gives the event and the fallout surrounding it a late, somber chapter in his book, not mincing words for Dolan but not attempting to mask his feelings at how much the entire thing hurt.

“I don’t know where all the negative energy comes from,” Oakley says. “When you play for someone for ten years, give your heart and soul and your sweat and tears every night, and someone does you like that, that’s bad.”

But it was a quieter sleight that stuck out in The Last Enforcer, and seemed to best encapsulate the complexities of its author. Oakley recalls that when he returned to Madison Square Garden with the Raptors for the first time, the tribute video the Knicks made for him ran at halftime, while he was in the locker room. He didn’t see it. Asked if he’d ever got to, and Oakley says he hasn’t, but more than that he’s not sure he wants to, “just because of how they did it.”

What makes Oakley so intriguing is what makes him so principled. A sense of fairness over pride, of looking out for those closest to you while being willing to open that circle up at any time to those in need. Compassion, in other words. He might be the last enforcer, but for what he’s advocating there should be hope that this book isn’t his last, because his story isn’t over.

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