CHICAGO — Dusty May and Nate Oats go way back. All the way back to the early stages of their coaching careers that crossed paths in Michigan.

Twenty years ago, when May got his start as an assistant coach at Eastern Michigan in 2005-06, he would make the 20-minute drive over to Romulus High School to watch Oats lead 6 a.m. workouts.

“I was a young assistant and still trying to learn the profession,” May recalled this week. “I’d go over and watch his team work out and we’d talk ball.”

After spending many years climbing the coaching ladder with several stops along the way, the two will cross paths again Friday, when May’s top-seeded Michigan squad squares off against Oats’ high-scoring Alabama attack in a Sweet 16 matchup at the United Center.

It’ll be a big-stage battle between a pair of coaches who developed a two-decade-old friendship when May invited Oats, among other colleagues, to spend a week watching the Chicago Bulls’ training camp.

“We’ve been friends since then,” May said. “I still go every year down to his coaching conference and we’ve shared a lot of thoughts. I’ve learned a lot from Nate. He’s a brilliant basketball coach and finds a way to be really good every single year, and that’s one of the most difficult things to do.”

Oats spent 11 seasons as the men’s head basketball coach at Romulus, where he made $4,700 a year. He led the program to a 222-52 record, five Class A Final Four appearances, a top-25 national ranking in three different years and a state title in 2013.

During his time at Romulus, Oats said he got to know hundreds of college coaches who came through his gym recruiting his players. May was among the many.

“Some of them you could tell were using you to try to get your players,” Oats said. “Some of them you could tell were great guys that were not using you to get to your players, and they were actually trying to build a genuine relationship with you.

“Dusty was one of those guys that was genuine, real, smart, and worked hard. … I liked him. I went over and tried to go to Eastern Michigan practices. We got to be very close because we were both young basketball junkies trying to learn every which way possible.”

When Oats made the jump to college and became an assistant coach at Buffalo, May was among those who endorsed Oats for the position on Bobby Hurley’s inaugural staff.

At the time, May was an assistant coach on Mike White’s staff at Louisiana Tech, and Danny White, Mike’s brother, was the athletic director at Buffalo. That connection paid off.

“I remember when Bobby Hurley was hiring Nate. He went to his AD and said, ‘I’m going to hire a high school coach,’” May recalled. “Danny called Mike and Mike asked me, ‘Hey, this is this is your friend. Can you put your name on him?’

“I said, ‘Absolutely. He’ll be as good or better than anyone that he can hire as an assistant coach at Buffalo.’”

After spending two years as Buffalo’s top assistant, Oats took over as head coach following Hurley’s departure to Arizona State. Once again, May was among those who backed Oats for the position and played a part in him getting his first head job in Division 1.

And it was a smashing success. In Oats’ four seasons at the helm, Buffalo reached the NCAA Tournament three times, earned its first ranking in the Associated Press Top 25 poll in program history and swept the Mid-American Conference regular-season and tournament titles in 2017-18 and 2018-19, which are the two winningest campaigns in school history.

“It was a seamless transition,” May said of Oats’ succession. “Once he got it, immediately, they were tough to play against, they were fun to watch.”

Then in 2019, Alabama came calling. Oats answered and made the jump to the high-major level.

Funny enough, his first win with the Crimson Tide came against May, who was in his second season as head coach at Florida Atlantic. Alabama laid down a 19-point beating on May’s Owls in Oats’ second game in charge.

“We talked for a long time after the game,” May said. “I remember he gave me a couple of things that I thought helped spur some thought in what we were doing and how we could do some things better.

“On a number of fronts, that game helped us. I remember more the conversations after when we went through the film and talked about things more than I do the actual game, because we didn’t play very well.”

May went on to turn Florida Atlantic, a program with little history of success, into a consistent winner during his six-year run. The Owls made back-to-back NCAA Tournament appearances for the first time ever, highlighted by a memorable Final Four run in 2023.

May was hired at Michigan in March 2024 and delivered two banner seasons. He won the Big Ten tournament title and reached the Sweet 16 in Year 1. This season, the Wolverines won the outright Big Ten regular-season title, tied a program record with 33 wins and reached the second week of the NCAA Tournament again.

“I think Dusty has not let his ego — he's the same guy that I knew as assistant at Eastern Michigan,” Oats said. “With all the success he's had, his ego hasn't gotten any bigger, and I think that speaks a lot to the character of the guy.”

Oats, meanwhile, has taken Alabama to new heights. He guided the Tide to a top-10 ranking and an NCAA Tournament appearance in six of his seven seasons, including four consecutive trips to the Sweet 16 for the first time in program history and the school’s first Final Four in 2024.

Throughout his time at Buffalo and Alabama, May would tune in to watch Oats’ teams play because he knew was going to learn something, like the time Oats took a concept from a European team, made it his own and executed it even better.

“Did I think that he’d get to this point? You never can guesstimate this,” May said. “But I knew watching his practice and his workouts that this guy knows ball. He knows what he’s doing.

“I think he's one of the best coaches on the planet regardless of league, level, affiliation. It's an honor to share the same sideline with a guy that does his job as well as Nate does.”

Along the way, Oats became the fastest coach to reach 100 wins with the Tide and May became the fastest coach to reach 50 wins with the Wolverines.

Not bad for two coaches who have come a long way since their Michigan days and have soared to the top of their profession — which is something neither saw coming 20 years ago.

Meeting in March Madness with a spot in the Elite Eight on the line? It’s about as unreal as that trip they took to the Bulls' training camp way back when.

“That's probably a surreal moment as a young 26-year-old third assistant in the MAC and a local high school coach who are now back in the same city competing against each other on this stage is pretty surreal,” May said. “But that's what makes this all so ironic. I don't know how it happened.”

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