A look at Raptors’ historic journey from outsiders to title contenders

Brad Fay and Michael Grange break down the history and the moment the Toronto Raptors find themselves in.

TORONTO — Before we look ahead — and there’s an inherent risk at looking too far ahead — it’s always worth looking back.

First, though, this is where we are:

On Saturday night in front of the 233rd-straight sellout crowd at Scotiabank Arena and what will almost certainly be the largest television audience to ever watch a basketball game in Canada, the Toronto Raptors will host the Milwaukee Bucks with a chance to earn a trip to the NBA Finals for the first time.

Nothing is guaranteed and, given the Raptors’ history, it’s probably wise to only let hopes get so high.

The Bucks are an elite team with an emerging superstar in Giannis Antetokounmpo and tremendous roster depth. They are the No. 1 seed in the league, were the pre-series favourite to win the Eastern Conference Finals and, were it not for Toronto’s refusal to die in double-overtime Game 3 and thus avoid falling behind 3-0 in the series, the Bucks would likely be trying to close out the Raptors if they hadn’t already.

But the Raptors somehow managed to claw their way out of a shallow grave, win a Game 4 despite a momentarily diminished Kawhi Leonard and then were elevated by yet another in an incredible line of wondrous playoff performances by Leonard as they stole Game 5 in Milwaukee.

The Bucks hadn’t lost three straight games all season before Thursday, and if Toronto can make it four consecutive wins they can move on to the NBA’s most hallowed stage.

Worst case? They lose and get to try their luck in Game 7 in Milwaukee. Generations of Raptors fans could only dream of such a chance.

So, a refresher for those who have only known the Raptors over the last six years — the era of plentitude — when playoff appearances have become routine, 50-win seasons the norm and the primary disappointment was your all-stars weren’t able to beat LeBron James and his all-stars in the playoffs.

For most of their existence the Raptors were the poor cousin, the unwanted step-child, an occasional laughing stock — and that was just in Toronto.

League-wide they were known for many years — and not fondly — for their dinosaur jersey and superstars that had left or were aching to get out of Dodge. Oh, and the lack of ‘the good cable’ in a strange land where your daytime sports TV choices were curling, curling or curling.

Granted, they had a point.

Seriously. Neck-and-neck with figuring out how to ease the tax burden for U.S.-based players in Canada was the rush to figure out how to set up reliable grey-market satellite TV packages. An executive once told me they had made progress in both areas as if they were of equal importance.

It was 25 years ago, on May 24, that former Detroit Pistons star Isiah Thomas, who was 11 days past his retirement as a player, burst through a paper logo and was announced as the team’s first general manager. He had no experience other than a reputation for orchestrating deals in his locker room, yet he was given a nine-per cent ownership stake — chew on that for a second — to build an expansion franchise from scratch. In Year 1 he put on the floor a rookie-of-the-year point guard in Damon Stoudamire, weighed down by a mixed bag of cast-offs, miscreants and Oliver Miller, who checked both boxes. They won 21 games.

Midway through what ended up being a 16-66 season in 1997-98, Thomas quit to take a job in television. Think about that: Things looked so bleak that Thomas walked away from an ownership position in an NBA franchise to do colour commentary for NBC. Whenever I feel badly about my retirement portfolio I think of Thomas’ decision and gain a small measure of comfort.

By the time Thomas moved on, the Raptors had played three seasons in a baseball stadium. Their best chances to win were Sunday afternoon games at 1 p.m. where the hope was visiting players would party too hard and not be ready for work. Sometimes it paid off. Other times it didn’t.

Damon Stoudamire as a Raptors rookie in 1995. (Frank Gunn/CP)

Legend has it a former Raptors head coach Butch Carter assigned someone to show Michael Jordan a good time the Saturday night before an early Sunday game. Jordan was going strong at sunrise but still easily took care of business on the floor a few hours later, after a brief nap and a cup of coffee, prompting Carter to scold his young team: “Michael was out all night and still kicked your ass. Now that’s a professional!”

For years the biggest moment in franchise history was a missed shot by Vince Carter, at the peak of his meteoric rise. His relationship with the team deteriorated so quickly he got traded to New Jersey for two guys named Williams, a draft pick that turned into Sam Mitchell whipping boy Joey ‘JOEY’ Graham (best NBA attribute? As a trained pilot, could land the team plane in an emergency) and Alonzo Mourning, who faked his retirement to avoid playing in Toronto. Two years later he won a ring in Miami, so… good call.

Toronto was looked upon like the franchise was in Reykjavik rather than south of Chicago, Milwaukee and Minneapolis. It was pre-Drake. Occasionally — errr, every single time — the club had to pay a premium to convince players to stay.

Imagine: the Raptors gave Antonio Davis a five-year $65-million deal in 2001. When I was waiting for him to change after games I would occasionally try to calculate his hourly wage in Canadian dollars, which were trading at about 65 cents at the time. I always got stuck on “Oh my God, that’s a lot of money.”

Despite the paycheque, Davis had concerns, among them his kids had to learn the metric system at their private school. The team responded by providing tutoring so players’ kids wouldn’t fall behind on US ‘culture.’

The corner-turning moment in more modern Raptors history — call it the middle years — came in 2006, when the club managed to hire Bryan Colangelo as president and general manager from the Phoenix Suns. At the time this was considered an incredible thing, a breakthrough of the highest order, a coup. It was, of course, before Twitter.

But even now a lot of the great moments of the current Raptors era can be traced back to Colangelo. He traded for Kyle Lowry, for example, and drafted DeMar DeRozan and Jonas Valanciunas, who helped the team become relevant and then… well, anyway.

But it feels worth noting that a legitimate Raptors high point came early in Colangelo’s seven-year run, when the team won the draft lottery and, with the No. 1-overall pick, selected Andrea Bargnani.

Former Raptors GM Bryan Colangelo presents Andrea Bargnani with a jersey Bargnani was selected first overall by Toronto in the 2006 Draft. (Adrian Wyld/CP)

As much as current Raptors president Masai Ujiri deserves ladles of credit for helping grow a competitive team, build a robust organization, find the likes of Pascal Siakam late in the draft and ultimately pull the trigger on some gut-wrenching decisions — trading DeRozan and Valanciunas, firing Dwane Casey — dealing Bargnani to the New York Knicks for a future first-round pick may be his best move of all.

Advancing to the NBA Finals would surpass even that.

Amazingly, all that is behind the Raptors now. On Saturday night every NBA fan who cares will be watching Toronto try to take its next step against Milwaukee.

There is room for optimism because in Leonard the Raptors have the best player in the series, arguably the best player in the NBA and undoubtedly the best player they have ever had.

There is room for optimism because in the likes of Marc Gasol, Lowry and Danny Green, the Raptors are over-loaded with veteran hoops IQ. They also, to this stage, have applied all that savvy in executing a game plan that has corralled the Bucks’ Antetokounmpo.

There is room for optimism because the Raptors might well have the better team and are playing to their potential.

It all guarantees nothing, but one thing is for sure: as the franchise that for years could do nothing right readies for its close-up, no matter what happens, it won’t be the worst that has happened.

And the very best could be yet to come.

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