It’s been a bumpy road, but Dwane Casey has smoothed out every crease in his path to becoming the winningest coach in Raptors history, both on the hardwood and in life.

Four-and-a-half hours before tip-off Dwane Casey heads downstairs, to the basement of his three-story brownstone in midtown Toronto, and lowers the ironing board from the rack on the laundry room wall. The cover is baby blue with vertical stripes, a Christmas present from his wife, Brenda. She also bought him a new iron, a white T-fal, but he still prefers the silver Shark. After positioning the board on a narrow strip of brown carpet alongside his office desk, he grabs the steaming Shark and prepares that night’s ensemble: shirt, jacket, pants, pocket square. For the few minutes he guides metal over cloth, he is not the coach of the best team in the Eastern Conference and not the winningest coach in the history of the Toronto Raptors. He is his daddy’s grandson.

Casey was born to a young couple in Indianapolis and raised by his mother’s parents in northwest Kentucky, apart from his four younger siblings. The grandfather he called Daddy, Urey Miller, worked mornings at Elliott Cleaners in Morganfield and nights at Payne’s Cleaners in Henderson. Urey left home every day at 5:30 a.m. in a crisp T-shirt and creased slacks, dirty laundry under his arm. “I had one suit and he always made sure it was pressed,” Casey recalls. “We didn’t have a lot, but we had that.” On days his grandfather let him tag along to the dry cleaners, Dwane separated lights from darks, and afterward Urey rewarded him. He had one more shift, the graveyard at Bel Air Restaurant, where African-Americans were allowed to clean but not eat. As Urey mopped empty floors, Dwane gorged on ice cream and Coke.

He’d offer to iron sheets for his grandmother, Elizabeth, and later jeans for his wife. “Dwane,” Brenda reminds him. “They’re jeans.” He is not a neat freak. He just likes having something to smooth. As a fourth-grader at Morganfield Elementary, he waded through hostile white parents protesting the desegregation of the school, and then he defended himself against daily attacks from their children. “Those became some of my best friends,” he says, the first wrinkles removed.

He started coaching when he was 13, with the Morganfield Little League Cardinals, who toasted their championship over milk shakes at Dairy Mart. But his career was marked by far-flung detours: to a coal mine, a tobacco farm, a courtroom and a Japanese gym where he tutored both the men and the women. He sold a newspaper, chauffeured a governor, was exiled by college basketball and exalted by the NBA. Seven years ago on Biscayne Bay, he implemented a defense that helped change the sport, forcing teams to reevaluate conventional lineups, stilted sets and the definition of a good shot. This season he finally joined the freewheeling movement he spawned, and the Raptors sit atop the East.

Getty Images

Casey arrived in Toronto as head coach in 2011 after failed interviews with a third of the league. He nearly missed his introductory press conference, having left his passport in a suit jacket that wound up in a Dallas storage unit, but he sweet-talked an understanding customs agent at the border crossing north of Buffalo. Newspaper clippings helped his case. Casey and Brenda moved into a downtown apartment on the 52nd floor of a 54-floor high rise with a three-year-old, Justine, and a newborn, Zachary. Fire alarms sounded all night, and Diapers.com didn’t deliver. At Justine’s preschool drop-off, they saw only Maple Leafs sweaters. The Raptors ranked 30th in defensive rating, 20th in offensive rating and were trying to tank. Two years later they were still trying, trading everybody of significance except swingman DeMar DeRozan and point guard Kyle Lowry, whom they almost jettisoned until the Knicks backed out of the deal.

When Lowry and DeRozan led Toronto to the playoffs in 2013–14, no one was more surprised than the Raptors themselves, who rushed out the marketing slogan they’d reserved for the following season: “We The North.” Since that stroke of branding genius, Toronto has never won fewer than 49 games, a stretch Vince Carter and Tracy McGrady would envy. The Caseys moved to the brownstone in Summerhill, with a school at the end of the block and a ballpark where dads set up a pitching machine and order pizza. When Brenda hawked Raps gear from Dwane’s closet to raise money for the school last fall, she sold out in a day.

She calls him a hoarder, not of clothes but of notes, scrawled on everything from magazine covers to kindergarten paintings. Loose pages fill plastic bins in the basement, pick-and-rolls drawn for Gary Payton and pin-downs for Kevin Garnett, along with VHS tapes he doesn’t have a machine for. “I can burn them onto DVDs,” Casey argues, not that he ever will. “I guess I just like knowing where my thoughts are,” he says. He can always open the lid and retrace an improbable ascent, from south to north, the bottom of the basketball world to the top.

Casey is 60 but his wife is 40 and their children are not much older than Lowry’s and DeRozan’s. So the Raptors sometimes forget their coach was only the fifth African-American ever to play at Kentucky, a defensive-minded point guard who won a national championship in 1978 while spending summers cutting tobacco with a machete and cleaning rails at Island Creek coal mine. At lunch, he would dim the light on his miner’s helmet and nap 450 feet under the earth, rats scurrying beside him. After graduating in ’79, Casey landed a job with healthcare giant Humana, but it required him to move to San Diego. He scrambled back to Memorial Coliseum, where Cats coach Joe B. Hall was preparing for the arrival of a vaunted recruiting class, led by center Sam Bowie. Hall told Casey to stay in Lexington, live with Bowie and teach the gifted freshmen the 6-8-10 offense. The 6-8-10, which Adolph Rupp ran more than a half century ago, was complicated. A bounce pass to the elbow signified one play, an air pass to the wing another.

Casey had sales experience—he peddled ads in Clay County for The Cats’ Pause, a weekly newsletter about UK basketball—and connections. His grandmother was the caretaker for former Kentucky governor and senator Earle Clements, and Casey occasionally drove the elder statesman to functions. But the time he spent with Bowie and the other young Cats reminded him how much he liked to teach. These were not the Little League Cardinals. They were the best basketball players in the country, and as Casey moved up the coaching staff, it became his responsibility to sign them: Shawn Kemp. Eric Manuel. LeRon Ellis. Chris Mills.

“The unwritten rule in college basketball is the black assistant goes and gets the black players,” Casey says. “Don’t worry about the X’s and O’s. Just recruit.” Casey insists he was never marginalized at Kentucky—head coach Eddie Sutton, who succeeded Hall in 1985, typically asked him to run parts of practice—but peers throughout the industry were. So he drove to rival SEC schools to research scouting reports, then hustled back to campus for coaches’ meetings and stayed after practice for skill work. During the offseason, he helped train the Japanese national team when they stopped in Lexington. “You can’t allow yourself to get typecast as a recruiter, because that label sticks and carries,” Casey continues. “I fought it. I made myself learn the game and teach the game.”

He was interviewing for his first head-coaching position in 1989, with the University of New Orleans, when employees at Emery Worldwide freight services in Los Angeles claimed they discovered $1,000 in a package addressed from Casey to Claud Mills, Chris’s father. After the ensuing investigation, the NCAA placed Kentucky on three years’ probation and handed Casey a five-year show-cause penalty, essentially banning him from college basketball. Kentucky offered him a job in minority affairs, but he still wanted to coach, and there weren’t many places he could do it. Kyoto was one. Casey lived in the Grand Prince Hotel and took over a club called Sekisui Chemical. For his men’s team, he imported Kentucky alums, such as Cedric Jenkins. For his women’s team, he lured Joy Holmes, the mother of current Nuggets guard Gary Harris. When he wasn’t at the gym or the Prince, he was barnstorming on a bus through Nagoya and Osaka with the national team, wondering if he’d have to call Humana.

Casey sued Emery for $6.9 million, and after he settled the defamation case in 1990 the NCAA lifted his ban. It turned out Casey had been on the road when the package was sent—recruiting—and the only evidence found in the envelope was a videocassette of a high-school game Mills played. Casey ironed out his record, but not his reputation. “Nobody remembers the settlement and the proof,” he laments. “The perception is set.” When Western Kentucky interviewed him later for a head-coaching vacancy, the school president assured him that the UK case was old news. Then he sat in front of the committee. First question: “What happened at Kentucky?”

The NBA didn’t care. Every July, Casey returned from Japan and coached a mishmash unit in the L.A. summer league, headlined by the Clippers’ Gary Grant and Olden Polynice. He loved it. He didn’t have to recruit. “Dwane had an NBA personality,” recalls George Karl. “Humble with an aggressive mind.” On the summer day in 1994 when Karl interviewed Casey at agent Bret Adams’s office in Columbus, Ohio, the SuperSonics coach wore a T-shirt and shorts; Casey wore a meticulously pressed suit. Karl and Adams were friendly with Sutton, who had resigned from Kentucky at the same time as Casey but rebounded much faster, as head man at Oklahoma State. Sutton lobbied for Casey. Karl had already hired Tim Grgurich, an assistant under Jerry Tarkanian at UNLV, to his Sonics staff. Now he was throwing another life raft to another college castaway. “I have a real nervousness,” Karl says, “about the NCAA stopping good coaches from being good coaches.”

Three seconds remain in the fourth quarter on Feb. 23, the Bucks leading the Raptors by a basket at Air Canada Centre, and Casey calls timeout. The Raps’ closers sit in front of him, all except center Jonas Valanciunas, who stands. Casey calls 4-Keep, which starts with an inbounds pass from C.J. Miles to Valanciunas at the elbow. When Toronto acquired Miles in July, Casey called him that night and chatted for almost an hour, describing ways he could use the sniper as an inbounder. “You could tell he’d already been thinking about specific plays,” Miles says.

Valanciunas catches on the right wing and straddles the three-point line. He clutches the ball in his right hand and Miles rushes toward it. The Milwaukee defender assigned to Valanciunas, center John Henson, anticipates the handoff and leans toward Miles. He can’t let a good shooter get an open three. But as Miles glides by, Valanciunas fakes the exchange and drives down the right side. He has a head start on Henson, who tries to recover, but Valanciunas rises for the rare buzzer-beating dunk. “Ballsy call,” says Toronto guard Fred VanVleet. Not only is Valanciunas the slowest player on the team, Casey had to tell Lowry and DeRozan they were both decoys.

When Casey walks through the back door of the brownstone that night, Brenda is still awake. “Jonas got fouled,” she says. Henson did appear to hit Valanciunas’s left arm on the way up, but there was no whistle and the Bucks won in overtime. They used to argue after games if Brenda disagreed with a play or a substitution. A blonde from Seattle, Brenda grew up watching the Sonics at KeyArena, and after graduating from Pepperdine in 1999, she worked for Kauffman Sports. The agency used a valuation for NBA players called Tendex, and Brenda was in charge of calculating the formula. Nunyo Demasio, then the Sonics beat writer for The Seattle Times, introduced her to Casey when she was in town to visit a client, guard Emanual Davis. Their first date was at summer league in L.A. Their honeymoon was at the World Games in Japan.

Casey earned his first NBA head coaching gig with Minnesota in 2005, when Garnett’s skills had diminished but his expectations had not. After Casey started his second season 20–20, the Wolves fired him, and they wouldn’t hit .500 again for a decade. Casey landed in Dallas as a defensive coordinator, with more aging stars, and he wanted to devise a zone the Mavericks could use like an eephus pitch. P---y defense, players grumbled, and point guard Jason Kidd abandoned the zone if it allowed a basket. At training camp in ’10, Casey told the Mavs they were going to build the best zone in the league, and grousing continued. “I like to lock up, man-to-man,” Shawn Marion said.

Getty Images

“Trust me,” Casey replied. “We’re going to need this at some point.” The Mavericks spent 10 minutes on zone slides at every practice and deployed the zone for an entire preseason game in Chicago. Still, they used the zone sparing during the regular season, until the Finals against Miami. The Mavs had no one to match up with LeBron James and Dwyane Wade. Dallas was too old, too slow and too small in the backcourt. “It was finally time to whip out that f------ zone,” recalls former Mavs guard Jason Terry. Dallas alternated between a 2–3 and a man-to-man defense in which they sank guards to the elbows and bigs to the boxes. “Miami ran iso like 80% of the time with LeBron and D-Wade,” Terry recounts. “You beat me, here’s another guy waiting. You beat him, here’s Tyson Chandler waiting. There was nowhere to isolate and nowhere to kick out. Remember, they didn’t have Ray Allen then. LeBron had to shoot jump shots. And what was LeBron’s weakness at the time? Eighteen foot jump shots.”

After Dallas won Game 6, Casey walked Biscayne Boulevard back to the Four Seasons, fleeing champagne fumes. He does not drink. He called Brenda, nine months pregnant with Zachary. Their life, and their sport, was about to change. That summer the Heat overhauled its offense, surrounding James with marksmen, and turning those endless isos into high pick-and-rolls. Power forward Chris Bosh started playing center and jacking threes. Plodders such as Joel Anthony faded away. “That zone made me a better coach,” Miami’s Erik Spoelstra told Casey. The Heat captured the next two titles, trumpeting pace and space; the Spurs and the Warriors won the two after that, touting the same. “Everything was different,” Terry says. “It was all about movement and shooting.”

Even with Casey, hired a week after the Finals, the Raptors were unlikely holdouts. “I came here from Houston, where it was all pull-up threes, and he didn’t want that,” says Lowry, who joined the Raptors in 2012. “He wanted slow-down, mid-range, run the offense. For two years we were like this.” Lowry bangs his knuckles against each other. Lowry was headstrong, but Casey had been steeled for the challenge—by Garnett, Payton and Secretariat. At Kentucky, Casey drove recruits to Claiborne Farm, where Secretariat had retired. Trainers told him they had to muzzle the horse or else he would nip their hands at feeding time. “The great ones,” Casey concluded, “are edgy.”

The relationship with Lowry was something else to smooth. Casey loosened the reins, and over the past three seasons, the Raptors never finished lower than sixth in offensive rating. All that earned them, however, was a pair of beatdowns from James. After Cleveland swept Toronto last May, Raps president Masai Ujiri promised a “culture reset,” which sounded like he might fire the coach or detonate the roster. Instead, he charged Casey with modernizing the offense while developing the bench, populated by players 25 and under. Casey revisited his Dallas days and dusted off elements of Rick Carlisle’s system, called Flow. “It’s not so many play calls for Kyle, play calls for DeMar,” Casey explains. “It’s more random pick-and-rolls, move the ball side-to-side, read and react.” He used to bench Valanciunas for threes. Now he encourages the 7-footer to let fly.

Through the first two months of this season, Lowry flashed Casey his familiar side-eye, frustrated with kick-ahead passes that took the ball out of his hands. “I figured it out,” Lowry says. “It just took a while.” Lowry’s scoring average is down, from 22.4 points to 16.5, but the Raptors are 45–17, they rank fourth in offensive rating and their bench ranks first in net efficiency, according to hoopsstats.com.

Of course, James may still dropkick them off the CN Tower this spring, but the Raptors have at least entered his airspace. Lowry and DeRozan were both in L.A. for the All-Star Game last month, with Casey coaching Team LeBron. He met James’s 13-year-old son, Bronny, and gave his recruiting pitch for Kentucky. “I’ll probably get in trouble for that,” he said, and James howled.

Even in Canada, Casey keeps the bluegrass close. “We couldn’t hit the side of the barn with a bass fiddle,” he tells the Raps, gravel in his voice. “We couldn’t throw rice in the ocean out of a rowboat.” He is quick to laugh and quicker to cry. Brenda doesn’t think he should watch This Is Us because she fears the waterworks. Last season, during a practice in Washington before a game against the Wizards, Casey spotted former Georgetown coach John Thompson. He did not break down, but he bee-lined for Big John. “As long as I live,” Casey said, “I’ll never forget how you stood up for me.”

In 1989, at a Black Coaches Association meeting in Dallas, Thompson addressed an NCAA official in the room: “If you think this guy is the problem with college basketball,” Thompson boomed, pointing at Casey, “you’re crazy.” The business was deserting him, but one outsized ally remained.

“Does that make you want to stand up?” Brenda asks, nearly 30 years later, sitting in their living room over a plate of macarons. She is raising children in a city where so many of their classmates are biracial they don’t even know the meaning of the word. But she recoils at the coded language often used to describe African-American coaches: Communicator. Connector. Father figure. In college, it is more than a stereotype. It is a job, befriending African-American players and signing them. Some assistants are gone most of the week recruiting and back on game days, exposed to amateur basketball’s underworld, the risks and temptations. All four assistants currently facing federal charges in the FBI’s college hoops probe are African-American. The more common punishment, however, is a pigeonhole.

It takes an iron man to dig out.

“I hope I can stand up and be an example that helps change the narrative,” Casey says. “ ‘He understands the game from a technical standpoint. He can teach the game. He can change an offense. He can put in a zone. He can do more than recruit.’”