I think it's fair to say his whole career pre-Pistons has turned out to be a series of "hindsight is 20/20" moments as each team has given up on him or gone in a different direction for whatever reason. This one stands out though because he was on the cusp of the player he would soon become:
In the playoffs, against a loaded Dallas team, Chauncey averages 22 points, 5.0 rebounds and 5.7 assists, and although the Wolves are swept, his timing is stellar. He's a free agent now, and learns he has a secret admirer: Detroit GM Joe Dumars. Dumars offers him $4.5 million, the mid-level exception, which the Timberwolves are willing to match. But there's a caveat: G.M. Kevin McHale tells him, "I have to be honest. Terrell's still our starter."
That's not to disrespect or take anything away from Terrell Brandon of course. He was a proven vet and once Mark Price was traded to Washington in 1995 he stepped into the starting role fulltime and established himself as a fine point guard for the next phase of his career. But his career came to a grinding halt due to injuries very soon after that while Billups' career has obviously taken off, so I would suggest it's a decision that Kevin McHale would like a mulligan on.