Sometimes you get one good chance. One proper attempt. If you’re lucky, you can weather the storm and grab a second, but usually it just boils down to one sterling opportunity to make things work in this league.

Most general managers, be they new hires or incumbent holdovers, are usually afforded one franchise-type talent in their attempt at the ring. These talents don’t have to be as prominent as a LeBron James(notes) or come as hyped as a Greg Oden(notes), but there are enough talents to go around and give each of these personnel bosses one with which to work. Then, with the patience of ownership and a short window of cap space and pre-contract expiration for the star in question, the GM gets one chance to get it all right.

Bryan Colangelo didn’t get it all right with Chris Bosh(notes). Actually, he got most of it wrong. And this is why Bosh, in Colangelo’s own words, is “likely” to leave Toronto sometime this summer.

Which is a shame, because Toronto itself didn’t really do anything to deserve losing its best player without compensation. The Raptors fans remain rabid and intelligent; a good decade after quite a few of them remained, well, rabid. Playing at the Air Canada Centre, even if you’re pulling down one win for every two tries, seems like a pretty worthwhile experience.

And those crowds took to Bosh in an instant. Perhaps in part because of Vince Carter’s(notes) thoughtless reaction to Bosh’s drafting in 2003, wishing publicly for veteran help instead of a green 19-year-old. After three years of disappointments, whatever doesn’t work for Vince, Raptors fans likely concluded, definitely works for us.

Bosh was a star. Sure, he had issues on the defensive end, and wasn’t contributing offensively at a level like James or fellow 2003’er Dwyane Wade(notes), but the guy could score from a position that’s hard to fill. And with former Suns GM Bryan Colangelo taking over in 2006 and a whole host of eventual cap space and high draft picks with which to work, Bosh seemed as likely as anyone to start playing two or three postseason rounds per year.

The problem was Colangelo’s execution, and the seeming arrogance that came with it.

The guy has more or less been revealed. And as damning as his big moves have been, the smaller ones tell nearly as big a story. The hiring of bit players whose names had been tossed around the NBA for a while, but ones that any scout with any salt tossed over his shoulder (or, perhaps, an understanding of advanced pro basketball statistical metrics) would have run far, far away from.

Luke Jackson(notes). Juan Dixon(notes). Cezary Trybanski. Fred Jones(notes). Even T.J. Ford(notes). Jermaine O’Neal(notes), though you can understand Colangelo’s attempt at giving the former Pacer another chance. Jake Voskuhl(notes). Like the guy, but come on — in 2008, Jake Voskuhl?

And, yes, the big moves were damning. Taking Andrea Bargnani(notes) first overall in a weak draft isn’t the worst thing he could have done, but bidding against himself to offer Bargnani an eight-figure yearly (once averaged out) contract extension years before he had to? That’s pretty bad. And arrogant. Handing Jose Calderon(notes), a fine player, nearly the same? With a trade kicker tossed in?

The O’Neal trade? Rare is the deal that sees you send out two centers who arguably (at least on a per-minute level, with defense thrown into the mix) outplay the one they’re traded for. And in O’Neal’s lone half-season with the Raptors, Rasho Nesterovic(notes) and Roy Hibbert(notes) (down in Indiana) were pretty close to that on most nights.

The killer was Hedo Turkoglu(notes). One of the worst deals of the decade, tossed at a 30-year-old (red flag) who was willing to leave a championship contender for a few extra million (there’s another red flag), who ducked out of a verbal agreement with the Portland Trail Blazers (so many of them, flappin’ in the wind), and who should have accrued a history of red flags in terms of production throughout his career. He was never nearly as good as Colangelo thought him to be, least of all not in a season that would see him turn 31 halfway through.

And with that, Colangelo blew his one chance with Bosh. Toronto isn’t completely devoid of talent. The Raptors are a nice team that will see a little bit of hopeful cap space next summer, and while they don’t reek of stardom (or even starting-dom, if I’m honest), kids like DeMar DeRozan(notes), Ed Davis(notes) and Solomon Alabi(notes) could help down the line.

Bosh, though, won’t be around for it. Never a dominant superstar, despite a pretty impressive turn to start last season, he’ll likely get to work his trade as the NBA’s finest second fiddle this side of the Staples Center. We should all be so lucky.

And Colangelo? He’ll have a little cap space to work with, and possibly the chance to do something great in a sign-and-trade with one of those average-sized expiring contracts he has on hand. But if he’s going to turn out in Toronto, he’ll have to take a step back and take a good look at the hubris that came with some of these moves.

He’ll have to. It’s not “likely,” but it doesn’t mean he doesn’t have to.

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