8 Difference-making players the Chicago Bulls signed past their prime

Since winning six NBA Championships during the 1990s in the Michael Jordan era, it’s been tough sledding for the Chicago Bulls. In fact, in the past 25 years since Jordan retired from the Bulls for the final time, Chicago has only made the Eastern Conference Finals once and only has tallied five total playoff series wins.

Part of their struggles has been bad injury luck and missing on draft picks, but another part has been missteps made in free agency. Over roughly the last three decades, the Bulls have had their fair share of free-agency misses – in which they have signed difference-making players who simply didn’t live up to their expectations or completely fell out of their prime as soon as they joined the Bulls.

Looking back, we explore eight players the Bulls signed (knowingly or not) past their prime.

Difference-making players the Chicago Bulls signed past their prime

8. Ben Wallace (2006)

After establishing himself as arguably the best defensive big in the NBA during his stint with the Detroit Pistons in which he helped them win an NBA Title, Ben Wallace decided to leave in free agency during the 2006 offseason. Wallace eventually signed a four-year, $60 million deal with the Chicago Bulls.

Wallace joined an already talented core (Kirk Hinrich, Ben Gordon, and Luol Deng) in Chicago but was clearly no longer the dominant defensive center he was in Detroit. He still had his moments for the Bulls, especially in the 2007 first-round playoff series against the Miami Heat, but battled knee injuries throughout his stint in Chicago.

The Bulls eventually traded Wallace to the Cleveland Cavaliers in a three-team deal less than two years into his four-year deal.