9. Richard ‘Rip’ Hamilton (2011)
Contract: 3 years, $15 million
Throughout the Chicago Bulls’ window of championship contention that lasted from 2011 to 2015, there was one universal constant you’ll find on these rosters. They were sorely missing an above-average shooting guard that could pull his weight whenever Derrick Rose wasn’t on the court. Signing Richard Hamilton in 2011 was Chicago’s attempt to directly address that flaw.
With money tight, the Bulls’ hands were largely tied as to who they could go out and get. Considering Hamilton was a three-time All-Star and former NBA Champion, he made sense as a potential fit. Rip signed on with a three-year, $15 million deal and was committed to the Bulls for most of their best seasons of this century.
Unfortunately, these were not Rip’s best seasons. In fact, they were the worst he’d ever looked on the court. In two seasons with the Bulls, Hamilton struggled to stay on the court due to constant injuries, playing just 78 total games and averaging 10.5 points and 2.6 assists while shooting horrible splits of 43.8% from the field and 33.7% from beyond the arc.
After those two incredibly disappointing seasons, the Bulls opted to waive Hamilton instead of bringing him back for the third year of his deal. After that, no other team showed interest on the market and Hamilton would retire. I think everyone can respect Rip for his legacy, but when it came to his time in Chicago, I’d rather just forget it.