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In the summer of 2009, free agent Ben Gordon was ready to earn a big contract after a stellar playoff performance vs. the Boston Celtics. On the series, Gordon averaged 24.3 PPG, as he and rookie Derrick Rose pushed the defending champs to seven games in the first round. 

The backcourts future was looking promising if they stayed in Chicago together, but the Bulls never negotiated a deal for Ben. Instead, he signed with the Detroit Pistons for five years, in between $55-60 million.

Unfortunately, Gordon’s tenure in Detroit would be nothing like Chicago, his numbers dropped and they never made a playoff appearance. He was traded to Charlotte along with a future first-rounder for Corey Maggette in 2012. Just a few years ago, Ben sat down to discuss his move to sign with the Pistons. 

(Via Streets First Podcast):

“I went to Detroit. That was the worst decision that I’ve ever made in my life, I said it. I loved Detroit. I loved it, but it was the worst decision I’ve ever made.”