#2 Chauncey Billups and Allen Iverson

In one of the most inexplicable moves of the 2000s, the Pistons traded away their star point guard who'd led them to 6 consecutive Conference Finals in exchange for a high-usage, low-efficiency player at that point. By 2008, there was little doubt in anyone's minds that Billups was the better player to build your team around, mainly because of his exceptional playmaking ability.

Joe Dumars, however, had designs on the free agency class of 2009, and Iverson's contract was an expiring deal along with Antonio McDyess', which would open Detroit up enough cap space to make a run. It is safe to say that the scenario he'd envisioned did not play out, as Iverson failed to meet his potential and got traded to the Grizzlies midseason.
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The Pistons finished with a below-.500 record for the season, while the Nuggets made it to the Western Conference Finals before losing 4-2 to eventual champions, the Los Angeles Lakers. Detroit failed to land any marquee free agent as well, and have made the playoffs just once since then.
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