Oakley has never fancied himself anything but a working man. He once described his role with the Knicks as that of "a butler in a mansion. I'm just happy to clean up and make sure everything is all right." That's one of the reasons he has been so loved in the cities in which he has played. He generously tips anyone in the service industry: locker room attendants, hotel maids, even waiters in restaurants where he has sent the food back two or three times (a not uncommon occurrence). "I like to let them know that I respect the job they're doing," he says. "I see them the same way I see myself."
In ways Oakley is not so much the last of his breed, as he is often called, but a breed unto himself. If you understand this about him, it's not so disorienting to learn that when he's not in uniform, he trades in his blue-collar persona for a silk-suit sensibility. Not that there's anything wrong with that—the league is full of clothes-horses—it's just that you don't expect Oakley to be one of them. He is just as comfortable discussing how to coordinate an outfit as how to set a pick. The closets in his spacious house in Toronto are the size of studio apartments, which is about right for a wardrobe that includes more than 200 suits, by his estimation, though the number is in a constant state of flux. "I usually won't wear a suit twice," he says. "If I do, it won't be in the same city. If I wear something in Toronto, the only way I'll put it on again is if I'm on the other side of the country or somewhere I can be sure that not many people have seen me in it."
Once he is done with a suit, Oakley usually finds it a good home. In the past, he sent dozens to players at Virginia Union, and last year he shipped a few to Bulls rookie Elton Brand because he judged him to be roughly the same size. Oakley has hundreds of neckties—he's a Zegna, Hugo Boss man—all tied in neat Windsor knots and hanging from racks. The floors of his closets are lined with shoes of every kind, with the notable exception of sneakers. Almost all those are at the Air Canada Centre, because he rarely puts on his work shoes anywhere other than on the job site. "I wear tennis shoes all year long when I'm playing ball," he says. "I don't want to wear them off the court."
Oakley has his own sense of style, which until recently tended to favor hues not found at Brooks Brothers. He has worn lime-green pinstripes with color-coordinated shoes and fedora, eggplant-colored jackets, bright orange three-piece suits. When Oakley was sidelined with a foot injury for 32 games in 1994-95, while with the Knicks, the Madison Square Garden crowd was treated to some of the most flamboyant pieces from the House of Oakley. Every night was Name That Color. "I didn't dress that way to stand out," Oakley says. "I did it because those colors looked good with my complexion and because that was the style at the time."
Yet he wants to be unique. The Knicks were playing in Miami one afternoon, and Oakley came down to the hotel lobby before the game wearing a suit the color of orange sherbet. Amazingly, he found teammate Chris Childs sporting the same ensemble. Oakley, mortified, went up to his room and returned dressed completely in black, which wouldn't have been unusual—if it hadn't been Easter Sunday.
When his work is done for the season, Oakley hits the road. Again, he sees no reason to take to the air, choosing instead to take long, often solitary drives that crisscross the country. "I drive probably 20,000 miles in the summertime," he says. "Some trips will be 4,000, 5,000 miles."
He will drive from Toronto to his hometown of Cleveland, then south to Alabama, where he has a sister, aunts, uncles and cousins, then anywhere. Chicago to see old friends. Florida to see his son. New Orleans just because. Most of the time, his only company is a collection of rap CDs. "Don't need anybody sitting next to me telling me to take this exit or that exit" he says. "Don't need anybody saying they need to stop to go to the bathroom."
This is Oakley the Grouch, showing that his disdain sometimes extends to human interaction. But then you learn that he throws lavish parties at Little Jezebel, the Manhattan restaurant in which he has a stake; that whenever he has a game in his hometown of Cleveland, he invites the entire team to come to his mother's house for a home-cooked meal; and that when he was a Knick and the All-Star Game was held in Cleveland, he sent a limousine to pick up the New York beat writers and take them out for a night on the town. You think you know me? What do you make of this?
Oakspeak: You know what they say about spilled milk—clean it up, go into the kitchen and get some more.
Julius Moss was 6'3" and barrel-chested, which was fortunate, because a man had to be strong to work a cotton farm in Alabama with not much more to help him than a couple of mules. It was the 1970s, and Moss obviously had more sophisticated machinery available to him, but he didn't see the need to change the farming methods he'd been using all his life. He had his grandson by his side, but there was only so much help little Charles Oakley could offer—he was still in grade school.