5 Worst Trades in Toronto Raptors’ history

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Dec 18, 2013; Boston, MA, USA; Detroit Pistons small forward Josh Smith (6) is congratulated by power forward Greg Monroe (10) and shooting guard Chauncey Billups (1) after hitting a shot during the fourth quarter of Detroit

#5. Jan. 21, 1999. In a complex multi-team deal, the Raps trade Chauncey Billups to the Denver Nuggets for draft picks.

Analysis: One might argue I’m cheating a little here, as this deal’s draft picks were used on excellent selections, but that’s beside the point. I call it a bad trade because of the player Billups was to become. The Raps’ brain trust didn’t realize what they had in Billups (and how cheaply he had arrived), and gave him away.

Result: The Raps ended up with Jonathan Bender, who was traded for Antonio Davis (a big win – Davis was terrific for several seasons, while Bender’s career was derailed by injuries) and a draft pick, who became Morris Peterson. But those wins occurred in the future, and were lucky. Giving up on Billups too soon was a major mistake.

Next: #4. A bromance backfires