On Friday, when the NBA announced the nominees for the league’s coach-of-the-year award, you’d have forgiven Raptors president Masai Ujiri if he took a moment to ponder a big question. Specifically, what would my team have looked like if I’d hired one of those guys?

That’s not to say Ujiri doesn’t have full confidence in the acumen of Nick Nurse, the rookie head coach who’s guided the Raptors to a 58-win season and the second trip to the Eastern final in franchise history. It’s only to say that, when you glimpse the list of the three finalists for the Red Auerbach Trophy, it’s worth noting that Ujiri considered two of them before he moved on to choosing Nurse.

It’s well known Ujiri interviewed Mike Budenholzer, now coach of the Milwaukee team that’s put a 2-0 stranglehold on the Raptors in an Eastern final. This was in the days after Ujiri, frustrated by a second straight playoff sweep at the hands of LeBron James and the Cavaliers, ended Dwane Casey’s seven-year tenure in Toronto by firing the eventual winner of the 2017-18 Red Auerbach Trophy.

Depending on whose version of the events you believe, Budenholzer was either a) always fixed on taking the Milwaukee job and only entertained other suitors in the name of leverage, or b) clearly wasn’t Ujiri’s choice from the opening moments of a rocky initial interview. So maybe Budenholzer never really wanted to coach in Toronto — which, it’s important to remember, hadn’t yet swung the franchise-changing traded that brought Kawhi Leonard to town. Or maybe Ujiri never wanted Budenholzer. And maybe both those things can be true.

Still, when you look at how Budenholzer transformed the Bucks this season, taking them from an eighth-seeded first-round flameout to an overwhelming favourite to make their first appearance in the NBA final since 1974, it’s difficult not to at least imagine how differently the highly organized Budenholzer might have approached guiding a Raptors team currently stuck in an offensive muddle of isolation-centric ugliness.

And it’s difficult not to at least imagine how differently things might be going if Ujiri had landed the first name on his list of post-Casey coaching candidates. That’d be Doc Rivers, the coach-of-the-year nominee coming off a turnaround season with the L.A. Clippers. Multiple NBA sources say that, as it became clear Casey would no longer be Toronto’s coach, Ujiri immediately gauged Rivers’ interest in the vacancy.

“When you’re at a crossroads, you go back to who you know best — who you trust the most,” said one source. And Ujiri and Rivers go back to Ujiri’s earliest days in the NBA, back when Rivers was the head coach of the Orlando Magic and Ujiri, in a meeting with Rivers and then-Magic GM John Gabriel, talked his way into a job as an unpaid scout.

“From day one, he took a liking to me, it’s amazing the connection,” Ujiri once said of Rivers, years ago. “There was a great bond, a great understanding … Every time something happens, he is the first to call me. He always encourages me. There’s always a message on my phone. To me it speaks tons about the guy.”

The Toronto job was Rivers’ if he wanted it, sources say. While Rivers recently signed a long-term extension to stay with the Clippers, at the time his long-term future with that franchise was cloudier. Still, in the months before the deal that sent DeMar DeRozan to San Antonio in the swap that snagged Leonard, the Toronto job clearly wasn’t viewed the way it would be with Leonard aboard. After a list of possibilities was exhausted, Ujiri replaced Casey with a guy who’d been sitting next to him as an assistant the previous five years.

Fast forward to the prospect of Sunday’s Game 3 in Toronto, and there’s nothing to say either Budenholzer or Rivers would be in a better predicament than Nurse, who’s coming off a blowout Game 2 loss that exposed so many of the limitations of Ujiri’s roster. Maybe you can’t fault a coach for looking down his bench and seeing no answers. Although Nurse’s strong suggestion in a Saturday conference call with reporters that he’s considering more than one change to the starting lineup does speak more to a reactive coach grasping in desperation than a proactive one operating a few moves ahead on the proverbial chessboard.

Still, the truth of the matter is this: Ujiri put the most promising team in franchise history in the hands of someone whose chief head-coaching experience came in the British Basketball League. (If you’re unacquainted with the hierarchy of overseas hoop leagues, let’s just say the list of European leagues widely considered superior to the British league goes deep.)

Nurse’s idea was to turn this season into a long series of experiments — to dabble in multiple lineups and newfangled rotations. And certainly he was at the mercy of one of the highest-maintenance stars in the league thanks to a load-management strategy that made Leonard’s nightly availability a perpetual question. But in turning the season into a test lab, there are costs, and it’s possible the Raptors are paying the bill against the Bucks. Toronto’s lack of identity is on full display here. Nurse insists he’s built a team with clear principles: Defend like hell and share the ball. But lately “Share the ball” hasn’t looked like much of an offence, especially when it’s often turned into “Here Kawhi — you take it.”

Milwaukee, though they’re also built around the spectacular talents of one star, has played largely the same way all season, an analytics-driven style with a disciplined focus on relentlessly mining basketball’s two most efficient scoring areas — shots at the rim and shots behind the three-point line — while eschewing almost everything in between. Perhaps as a direct result, their players play with an obvious and infectious clarity. If they’ve got a lane, they put a shoulder down take it. If they’re open, they mostly let it fly with confidence.

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Now, Nurse might counter that Milwaukee’s players are playing exactly how Toronto’s players ought to be. And to be fair, it’s tough to criticize a coaching staff when its shooters can’t make shots — or, worse, simply don’t shoot them. Danny Green, now on a four-playoff-game streak of invisibility, is so far at sea that it’s possible he’s lost his Game 3 starting job to Norman Powell. Ditto the suddenly haggard Marc Gasol, he of the 3-for-20 series shooting line, who at age 34 is making the plodding Serge Ibaka look like the more sprightly option at the five. It’s tough to kill a coach when a seven-man rotation is suddenly short two starters, and nobody’s doing that here.

But make no mistake: It has to have occurred to Ujiri, a harsh self-critic, that he put the best Raptors roster of all time is in the hands of a head coach who’s never done this before, not at this level, not under this kind of pressure. Ujiri’s a man who operates on instinct as much as anything, and it was never his first one to hire the rookie. But with the Raptors suddenly stuck in a daunting hole, it’s now up to the rookie to diagram an unlikely escape with a tool box short on options.

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