Standing at 9-19 with a third of the season complete is clearly something he didn't envision, but after almost seven years in charge, it's hard to see what he has ever envisioned for this franchise.
Colangelo came to Toronto prior to the 2006-07 season as the big-name front-office executive the Raptors were desperate for after the shortcomings of his predecessor, Rob Babcock. He was brought in to gain the Raptors organization a degree of respect—unseen since Vince Carter's prime—by making the Raptors consistent winners.
He is now into his seventh season with the Raptors, and it's safe to say that his efforts have been a major disappointment.
During his time as GM of the Phoenix Suns, they made the playoffs in 10 out of 12 seasons and won four division titles at a regular season-winning clip of 529-420 (.557).
With the Raptors, it has been a completely different story. Toronto has reached the postseason twice in six seasons, won one division title and compiled a losing record of 206-270 (.433), excluding this season.
The Raptors, despite their latest five-game winning streak, are headed towards yet another season without a playoff appearance.
And Colangelo has put them in this position.
The sad part is that this isn't even unfamiliar territory.
Now, I could go on forever about the major mistakes Colangelo has made, whether it be drafting Andrea Bargnani, giving up Roy Hibbert or signing Hedo Turkoglu. However, since most avid NBA followers are well aware of this, let's focus on the big picture for a minute.
There's one underlying factor that explains why he has made these mistakes: his pride.
Colangelo has chopped and changed the roster far too often. After winning 47 games in his first season, he introduced six new faces the next year. The third season saw 11 new faces at different points through its entirety, and then another eight new players the year after that.
There has been absolutely no sense of continuity, since he has been too caught up in replicating the success of that first season and his days in Phoenix.
After getting a good value for his money when he signed free agents Anthony Parker and Jorge Garbajosa in his first season, it seems as though he has signed players for the sake of using cap room.
Two wrongs don't make a right, and just because a player is available and would actually consider signing with the Raptors doesn't mean he fits the needs of the roster.
Landry Fields is a prime example of that right now.
Signing Fields was supposed to eliminate the New York Knicks from the Steve Nash sweepstakes, but Colangelo never once considered the possibility of "Plan A" failing. He has always looked for the quick fix instead of setting a long-term goal that would create the best opportunity for success.
All this stems from a man who was too proud to trade one step back for two steps forward.
He keeps trying to place importance on making the playoffs season after season when the worst place to be in the NBA is between sixth and 10th place. There's virtually no chance of having luck go your way in the lottery at ninth or 10th, and you're most likely going to be eliminated in the first round of the playoffs if you're in sixth, seventh or eighth place.
What Colangelo needed to do was determine who was worth keeping, tear down the roster, suck it up for a few years and build a perennial winner. Add to that his inability to draft well, and it's easy to see why the Raptors are in their current predicament.
Another example of his pride comes from his inability to deal with certain players.
Bargnani hasn't lived up to the lofty expectations that Colangelo set for him. Bargnani and Chris Bosh never worked, and yet the GM chose to stick by Bargnani.
It's probably a good thing for Raptor fans that Bargnani made those disparaging comments regarding the Raptors—Colangelo might finally be able to let him go.
And then, there's Chris Bosh. While other franchises—like the Utah Jazz and Denver Nuggets—realized their franchise players would be looking to leave and got solid pieces in return, Colangelo's ego was too big to let him go, and he tried to find a way to make Bosh stay.
Oh, how wonderfully that worked out.
Now, the obvious question: Who could possibly take over the Raptors GM's duties on an interim basis without being rushed into the situation?
There are a couple of options here.
Wayne Embry already performed these duties once (prior to Colangelo's arrival) and would be a more than suitable candidate until the ideal person is found. Ed Stefanski is another option for the Raptors, as he is someone with experience from his days with the Brooklyn Nets and Philadelphia 76ers.
The Raptors need to do this as soon as possible, since newly signed free agents have been fair game for trades since Dec. 15. More importantly, the new GM needs as much time as possible to explore deals before the Feb. 21 trade deadline.
There shouldn't be too much concern about the draft, since Colangelo has done his best to ensure the Raptors won't have a first-round pick.
Whether it's internally or externally, the Raptors need to hire someone who can identify a clear path to long-term success for the Raptors. Someone who will accept that this is not a franchise that can just rake in free agents or pull off blockbuster trades to build a super team on the fly.
This is a franchise that needs to build through the draft and make sound trades that build on the core pieces.