Why does it seem like in the Bryan Colangelo era, the Toronto Raptors are forced to make big, franchise-altering decisions at the worst possible times? To whit:
June 28, 2006 - Armed with their first number-one overall pick in team history, Raptors face one of the weakest draft classes in six years. They ultimately select Andrea Bargnani, who has proven to be one of the stronger selections from that class, but he is not the franchise-altering talent that teams like Orlando, Chicago and the Clippers got with their first-overall selections.
June 30, 2006 - Feeling they needed a starting-caliber point guard, the Raptors trade their biggest trade asset, Charlie Villanueva, to Milwaukee for T.J. Ford, only to discover early in the 2006-07 season that Jose Calderon would emerge as a legit point guard in his second year, negating somewhat the need for Ford.
April 24, 2007 - Sam Mitchell wins Coach of the Year, ostensibly forcing the team to re-sign him as head coach despite the team's need for an upgrade at the position. His contract expired at the perfect time for the team to go out and hire a more experienced replacement to take the team to the next level, but Mitchell's COY award made losing him look like a worse PR gaffe than signing him back. He was fired eighteen months later.
July 9, 2009 - Armed with a truckload of cap space to use in one last attempt to field a competitive supporting cast for free-agent-to-be Chris Bosh, Toronto signs the best free agent on the market, Hedo Turkoglu, despite his age and questionable fit with the team. Despite the previous year offering guys like Josh Smith and Monta Ellis and the subsequent year offering the bounty of the FA class of 2010, 2009 was a weak year and the Raps were forced to buy in a seller's market in an attempt to retain their star. Hedo was traded away a year later.
Spring 2011 - Bryan Colangelo is up for a contract extension, but no one yet knows how well equipped he is to lead the Raptors through their current rebuilding process. That is the subject now up for further investigation.
Now, looking back at this abbreviated timeline, clearly not all of those decisions HAD to be made the way they were. They were made with due consideration and could have gone in different directions if the people in charge had wanted them to. However, it should be noted that at the time each decision was a lot harder to not do than to do, given what information was available when each was made. That doesn't mean each was a perfect decision that fate simply soured, it just means that sometimes you are forced to make a decision under less-than-ideal circumstances, and you are forced to live with that decision regardless. Sort of like what's happening now with Colangelo.
No matter what one thinks of how Colangelo handled the roster when he was attempting to build it around Bosh, the task he faces today and tomorrow is totally different, and very little of his ability to do the latter can be culled from the former. Building a team from scratch takes shrewd evaluation, it takes vision that extends beyond the next year or two and it takes an ability to not fall in love with potential over production. While Colangelo had to weigh more immediate gains when dealing with the team around Bosh, he has to look far further into the future with the team now. Can he do it? Is he equipped with the patience, foresight and adaptability that is necessary when building a team from scratch? We don't know, but MLSE must decide without knowing those things whether or not to extend his contract for another few years.
It would almost be easier if Colangelo had been a disaster in his five years with the club. It would help if he'd taken Adam Morrison or Tyrus Thomas number one overall in 2006, or if he'd been unable to extricate himself from that Turkoglu deal last summer. Then shoving him aside would be an easy choice, but that's not the way things went down. He's shown glimpses of what made him such a desirable GM five years ago, and it stands to reason this would not be such a fierce debate had his near-trade for Tyson Chandler had gone through this summer. Even still, he's proven to be talented in the last two years at grabbing strong second-tier building blocks like Amir Johnson, DeMar DeRozan and Ed Davis, and he hasn't panicked and ruined the team's flexibility going forward by making a short-sighted trade with the Traded Player Exception he got in the Chris Bosh sign-and-trade.
On the flip side, though, he hasn't managed to acquire a single legit star in his time with the club - not in free agency, through a trade or in the draft - and while getting a legit star is not easy, getting those kinds of players to your team is part of the job of managing a professional club. It's not easy, but that's why they pay him the big bucks. Plus, now that Colangelo's former underling Masai Ujiri just got a healthy bounty by unloading Carmelo Anthony before he hit free agency, the questions will arise again as to why Colangelo didn't get more for his former franchise player when he had the chance. A lot of his job is handling how people perceive his work in hindsight (as opposed to judging his work based on the circumstances facing him when he made his decisions), and right now he's got a lot to handle at that end of the spectrum.
In spite of that, though, the odds that he DOESN'T receive a new deal with MLSE are slim. He's overseen a relatively profitable enterprise during his tenure and his roster management hasn't been bad enough to necessitate a replacement. Would everyone like a better idea of how good Colangelo will be at steering this ship through these troubled waters? Of course. They'd love to wait and see how this draft plays out (of course, it's another weak one), and they'd love to see how he ultimately manages his TPE and free agency. The bean counters would especially like to see how well Colangelo has positioned this club to weather the upcoming changes to the Collective Bargaining Agreement. A choice on his future has to be made before any of those things happen, though, so in true Raptors fashion a decision affecting the future of the club will have to be made at the worst possible time to have to make it.
Throughout Colangelo's time in Toronto, his two best players remain those that have been acquired by someone else (Bosh and Calderon) and while DeRozan and Davis offer promise for the future, Colangelo's got a lot of work to do to better the talent in front of them to make the Raptors relevant again. I've maintained for a while that one cannot being to accurately assess his job of setting the Raptors up for the future until he's had the chance to go through one draft and one off-season completely free of the Chris Bosh era, but if we get the chance to evaluate him after those instances then that means that he's going to be around for a lot longer, regardless of how well said evaluation turns out.
Nothing ever seems to happen at the right time for the Toronto Raptors.