Icon Sports MediaHe was the Sun God. The Golden Child. There wasn’t a more respected NBA front office executive than Bryan Colangelo during his 15-year tenure in Phoenix, 11 of those years spent as the team’s GM. While the Suns never ended up securing the NBA title, Colangelo built a consistent winner that made trips deep into the playoffs on numerous occasions. He also showed to have a good eye for young talent, getting Michael Finley, Steve Nash, Shawn Marion, Amare Stoudemire and Leandro Barbosa from the NBA draft despite never drafting higher than ninth. 
So when Colangelo fled north to Toronto to become the team’s GM and President in February of 2006, it was considered a coup for the Raptors. Jerry Colangelo’s Golden Child was sure to bring some sunshine up north to Canada with him.
"I'm hoping to change the image of a great organization and great city," the younger Colangelo told USA Today shortly after being hired by the Raptors. "It's ripe for a lot of growth." 
An image change was definitely in order for the Raptors, whose “good old days” consisted of an Eastern conference semifinals appearance in 2001 (they lost to Philadelphia in seven games). In the franchise’s 11 campaigns B.C. (Before Colangelo), Raptors’ fans only got to enjoy three winning seasons and one playoff series victory (in three tries). And to add salt in the fans’ wounds, all of the team’s stars – Damon Stoudemire, Marcus Camby, Tracy McGrady, Vince Carter – couldn’t wait to bolt back across the border once given the opportunity. 
We’re quickly coming up to the five year anniversary of Colangelo’s pledge to change the Raptors’ image – so perhaps now is a prime time to assess his time spent up north? So how has Colangelo done? As the French Canadian would say, “Comme ci, Comme ca” (“so-so”). Colangelo certainly seemed to have a King Midas’ golden touch when he first arrived in Canada, spurring the team onto a 20-win improvement his first year there, earning himself 2007 NBA Executive of the Year honors. But after posting winning records those first two years and making the playoffs, things have gone back to usual for the Raptors – middling win totals, star players leaving town.
The most recent star to leave the country was of course Chris Bosh, who took his talents to South Beach. But that wasn’t necessary a bad thing, and Colangelo is wise enough to realize that.
“Even if there was an open market similar to what’s gone on with [Carmelo Anthony] last year and Chris Paul this year and Dwight Howard, he’s not that caliber of player,’’ Colangelo candidly told the Boston Globe last week. “It’s just that simple. I never had an opportunity to move him for the kind of haul that some of these other deals are producing. But for us to end up with a couple of first-round picks, it was a nice way to segue toward the future. As long as we weren’t strapped with a $126 million contract and the inability to really build around the player, we feel like this is probably the best thing that could have happened to us.’’
However, while it is true that Bosh probably isn’t a “franchise player” to build a team around, his leaving does continue the ugly trend of stars leaving Toronto and sends a message to other star players: “you don’t want to play here”. That message seems to have always been loud and clear to NBA players, as Toronto has never been able to lure top-level free agents to come up north. The franchise’s biggest free agent signing (technically it was a sign-and-trade) was when Colangelo brought in Hidayet Turkoglu in 2009, and that turned out to be an unmitigated disaster and Turkoglu was sent packing a year later.
So perhaps the question shouldn’t be whether Bryan Colangelo can change the image of the Raptors and build a winner, but rather can anyone accomplish that feat? While the city of Toronto has plenty to offer a potential free agent – it’s one of the league’s biggest markets, it’s incredibly ethnically diverse, it’s the only NBA team in the country so players can become national celebrities (and get national-level endorsements) – there are also some unique drawbacks to playing in T.O.
Foreign Land, Funny Money
Generally speaking, there really aren’t too many cultural differences between living in Canada and the United States. Still, Toronto is in a foreign country as opposed to the other 29 teams in the league. While that isn’t a big deal to non-American players, it can be a hindrance to signing big name Americans. After all, no kid grows up in the States dreaming of being a basketball star in Canada.
No ESPN
Canada offers numerous all-sports television networks, including NBA TV Canada, which caters almost exclusively to the Raptors. However, ESPN is not available up north. While that might sound like a silly and trivial reason to not want to play in Toronto, it is one that players have complained about in the past. Guys want to be able to see the highlights of themselves on SportsCenter, not SportsCentre (on Canada’s version shown on TSN).
Second-Class Citizens
No matter how successful the Toronto Blue Jays or the Toronto Raptors are, Canada will always be a hockey country, with Toronto serving as its heart. Despite the Toronto Maple Leafs not hoisting a Stanley Cup since the 1960s, they still run the sporting scene in Toronto. This becomes an even bigger deal when you consider that the Leafs and Raptors are owned by the same company and play in the same arena. Colangelo will have to convince any potential signing to accept being something he probably has never been before in his career – a second-class citizen.
Bring a Jacket
There is still the stereotype out there that Canada is a frigid, barren land where winters last 11 months of the year and the sun is only a rumor. The truth is that the weather in Toronto isn’t any different than any U.S. eastern/midwest city. But it is still cold (and snowy) during basketball season, so the weather will become a weakness in the GM’s free agent pitches, rather than the strength it was in his previous job.
While the franchise is winning games at a higher clip than before he came aboard (0.392 before, 0.444 after Colangelo), Bryan Colangelo has still not made the Raptors a winning organization. This year is no different, as the team is expected to be amongst the worst in the NBA. And, while they have some nice young players, they are still devoid of a piece that they can build the franchise around. But with another lottery pick on the way in June (from a draft class expected to be very deep) and salary cap space opening up this summer, the time is coming for Colangelo to prove his worth. How he navigates the next couple of years – and the numerous hurdles to running a NBA team in Canada – will determine his legacy. Was his success in Phoenix thanks largely in part to his father’s involvement, or is Bryan Colangelo really the Golden Child?
Jeff Fox runs The Hoops Manifesto. He can be reached on Twitter at @HoopsManifesto.