5. Ben Wallace (2006)
Contract: 4 years, $60 million
As the second former Piston to sign with Chicago on this list, it’s clear the Bulls respected Ben Wallace and everything he was helping build in Detroit in the early 2000s. Wallace won four Defensive Player of the Year awards and led the NBA in rebounding several times in the five years leading up to signing with the Bulls, so easy to see why they’d value his talents so highly.
Signing a four-year, $60 million deal, this was arguably the biggest free agent signing in franchise history at the time. The Bulls just never had a player of Wallace’s caliber on the team since MJ and Pippen. Fans were ready for Wallace to come in and make a big impact, and that’s exactly just what he did… at least, at first.
In his first season with the Bulls, Wallace averaged 6.4 points, 10.7 rebounds, and 2 blocks per game en route to qualifying for his sixth (and final) All-Defensive Team. He even helped the Bulls win 49 games and actually win their first playoff series since 1998, until they were bested by his former team in Detroit in the second round.
Unfortunately, Wallace’s offensive production began to drop off a cliff at this point. When you also consider the fact there were reports of friction with Scott Skiles and the up-and-coming young core of Kirk Hinrich, Luol Deng, and Ben Gordon, Wallace was the easiest piece to remove from the equation. Wallace would be traded away before even getting halfway through his original contract.