I've always considered the drafting of Rafael Araujo the Raptors' original sin. It set off a chain reaction the team has never really recovered from.
Araujo, as every Raptors fan knows, was picked No.8 overall by Rob Babcock, who promised on draft night that the big Brazilian was "Not a stiff.''
Well, he was a stiff. One with small hands and short arms and - quite literally - no upside.
Missing at No.8 isn't ordinarily the end of the world. It happens. And it says A LOT about the NBA that having the chance to pick the eighth - or in this year's draft - the ninth best player in the world in a given year carries with it no certainty of success.
But the 2004 draft had its share of good players. One of them - Andre Iguodala - was taken ninth by the Philadelphia 76ers, as every Raptors fan knows.
Which is the problem: It's not so much that Araujo was a bust, it's that Iguodala represents exactly and - short of Kobe/LeBron/Wade - I mean exactly what the franchise needs.
He slashes. He defends other wings. He's a one-man fastbreak. He's a passable spot-up shooter. He's very good playmaker and passer. He's relatively affordable, at $12-million a year, which is pretty good value for a Tier 1A wing player in the NBA.
But you know all this.
Still, I've been thinking about Iguodala as I've watching Mickael Pietrus with the Orlando Magic.
Even after Colangelo arrived and engineered the 2006-07 turnaround, the Raptors were still well short athletically on the wing. They needed some speed and toughness on the perimeter, and they had the full-mid level exception to shop with.
Here were the options as I outlined in a story setting up the free agent signing period two years ago:
* Matt Barnes, Golden State Warriors. An unrestricted free agent at the age of 27, the 6-foot-7 small forward had a breakout year playing for Don Nelson, with averages of 9.8 points and 4.6 rebounds a game on 43.8-per-cent shooting in 24 minutes a game. He stands to get a big raise from the $744,000 he was paid last season.
* Jason Kapono, Miami Heat. He's not the most athletic small forward in the league, but he makes up for it with spectacular three-point shooting. He led the NBA at 51.4 per cent. He's 26 and averaged 10.9 points a game, opening the floor for Shaquille O'Neal and Dwyane Wade.
* Mickael Pietrus, Golden State Warriors. As a restricted free agent, the 25-year-old could be available because the Warriors might not be able to sign both him and Barnes and stay under the luxury tax. An athletic six-foot-six wing player known for his defence, Pietrus averaged career bests of 11.1 points, 4.5 rebounds, 48.8 per cent shooting and 26.9 minutes.
* James Posey, Miami Heat. He's the oldest and most experienced player who might be available in this range. Posey will turn 31 in January, but has earned a reputation as a hard-nosed defender. With a team-first approach, his credibility was bolstered by the championship ring he won with the Heat in 2006. He averaged 7.7 points and 5.1 rebounds in 27 minutes a game last season.
It turns out Kapono was the Raptors first choice. They laid $24-million on him over four years, and there's not doubt Colangelo regrets it.
In some ways this is the Raptors second major sin, and certainly the primary blunder of Colangelo's since he joined the club in 2006.
Posey was heading to Boston - or at least a contender - regardless. So really it was choice between Barnes, Kapono and Pietrus. Barnes and Pietrus ended up with qualifying offers in Golden State. Kapono got paid. Barnes eventually found his way to the Suns, Pietrus finally got his mid-level deal this past summer from Orlando.
And watching Pietrus so far in the playoffs for the Magic it's hard to understand why a good shooting, athletically challenged team like Toronto at the time opted to add another good shooter who was defensively challenged.
Pietrus slashes. Pietrus defends. He can make the odd play. What he's done in the playoffs for the Magic - he's averaging 14.8 points a game and shooting 48.6 per cent from the floor while chasing LeBron around - is something the Raptors could still use.
And now the Raptors head into another off-season and another draft looking for something that keeps slipping through their fingers.
Talked briefly with Henry Thomas, who represents Chris Bosh and Anthony Parker and had little luck getting him to lay his cards down, which is hardly surprising. Thomas is kind of an interesting guy in the agent business. He goes pretty light on recruiting, emphasizes serving the clients he has. Substance over style. He said he plans to meet with Colangelo in Chicago but that it was "early in the process." More pressing is trying to get a guage on Anthony Parker's immediate future. Thomas said he's had some feelers from Europe, but nothing concrete yet. "I expect there will be some interest from the usual suspects,'' said Thomas. "And he owes it to himself to listen to whatever their may be alongside whatever interest there is from elsewhere in the NBA, alongside Toronto.''