For all that can be said about the deficiencies plaguing the on-court product, the front office hasn't fared much better. For the league's elite teams, there has been a proven way to build a roster, and the Raptors haven't done anything close to it.
The NBA's two most recent champions reached the league's pinnacle in surprisingly similar ways. The Celtics and Lakers each had a perimeter star in his prime (Paul Pierce and Kobe Bryant, respectively), but each lacked a big-time post player to be a secondary scorer and to anchor the defense Boston was able to use an armory of trade pieces (Al Jefferson, an approximately $13 million expiring contract, and two first-round picks) to acquire Kevin Garnett, who became the 2008 Defensive Player of the Year as the team romped to 66 wins and never looked back.
During that season, Los Angeles traded the rights to Marc Gasol, an approximately $9 million expiring contract in Kwame Brown, and two first-round picks for Pau Gasol. Since then, the Lakers have won the 2008 Western Conference Finals and the 2009 Finals, and are currently the top team in the West. While the Celtics gave more for Garnett, commensurate with the future Hall of Famer's higher trade value at the time, the trades are uncannily similar. Indeed, the Pistons' 2004 pickup of Rasheed Wallace en route to their championship that season followed roughly the same pattern – the team traded expiring contracts and a first-round pick.
For those wanting the Raptors to become a contender, or wondering why marquee franchises land the Garnetts and Gasols of the world while the Raptors don't, look no further than the accumulated asset bank. Danny Ainge had spent his tenure as general manager tirelessly seeking draft picks and young talent in order to have the kind of stockpile that would allow for such a trade. Even in a trade as maligned as the one that sent Shaq to Miami, the Lakers managed to win back a first-round pick, along with two young players in Caron Butler and Lamar Odom. One of the picks in the Garnett deal, ironically enough, was a pick that Minnesota had given Boston in a prior trade between the teams.
The trend is that in order to have the vaults of picks necessary to pry a disgruntled star from a rebuilding team, those picks have to be acquired in the first place. The Raptors, conversely, have a history not of obtaining extra draft picks, but of trading them away.
Due to being left with draft pick debt that cost the team its first-rounder in 2007, and then his decision to ship the 2008 pick in the T.J. Ford/Jermaine O'Neal trade, Bryan Colangelo will be making only his third first-round selection this coming June despite having been with the team since 2006. Had the Raptors made the playoffs, their pick would have reverted to the Heat, the consequence of Colangelo's inclusion of it in the Jermaine O'Neal/Shawn Marion trade.
What was essentially two first-round picks to turn T.J. Ford into Shawn Marion became disastrous, as the team used its new-found opportunity to land Hedo Turkoglu for $53 million over five years. Turkoglu's contract has emerged as a noose for the team, while his on-court production has suffered considerably. Even though it would be tempting to trade a pick or two as enticement for a team to pick up Turkoglu's contract, the team would be back into pick debt. Even a basic contract dump would be virtually impossible at this point, let alone a deal that could convert Raptor futures into a promising present.
Even more disconcerting is that the Raptors haven't historically been in the market for extra picks. In the 2001 trade that sent Corliss Williamson and scraps to Detroit for Jerome Williams and Eric Montross, for example, the Raptors were the team giving up the draft pick despite also trading the best player in the deal. While the spirit behind gaining Lamond Murray the following year was admirable, the Raptors yet again traded a first-round pick in the exchange.
Only the Damon Stoudamire for Kenny Anderson and Alvin Williams trade, in which the Raptors received two first-rounders and a second-rounder, really stands out among the heap. That trade, of course, was all the way back in 1998.
The soon-to-be-expiring contracts of Reggie Evans ($5,080,000) and Marcus Banks ($4,847,586) allow for a little more hope, but not much. Of the many types of players the Raptors have traded during their 15-year history – the sulking star, the over-the-hill pint-sized point man, the overpaid benchwarmer – the expiring contract has not typically been one of them.
A long line of talented expiring Raptors, from Donyell Marshall to Mike James to Morris Peterson, each could have fetched something of note in a trade. Naturally, the Raptors let all of them walk without receiving anything in return... not even, say, a low first-round pick.