Worst Cavaliers free agent signings No. 15: Henry Sims, 2013
In 2013 the Cleveland Cavaliers were ready to push for a winning record. They had built a youg core up after LeBron James’ departure, headlined by Kyrie Irving, and wanted to add pieces to propel them forward. They focused on the center position particularly, signing Andrew Bynum and Henry Sims to free agent deals.
Bynum was in the midst of an injury-riddled tailspin for his once-promising career, and Sims was entirely inept as his backup. He averaged just 2.2 points and 2.8 rebounds per game, and the Cavs’ offense cratered whenever he was on the court. It was so bad that at the trade deadline the Cavs sent Sims, Earl Clark and a future pick that would become Jerami Grant to the Process Philadelphia 76ers for center Spencer Hawes, just to be respectable at the position.
Worst Cavaliers free agent signings No. 14: Mike Woodson, 1990
All of the other 14 players on this list were signed to full-season contracts, but in 1990 a veteran shooting guard named Mike Woodson — the same one who would go on to – signed a deal in mid-December with the Cavaliers hoping for one last ride in the NBA.
Woodson didn’t last two weeks, giving the Cavs one of the worst runs of any player signed to any team as a free agent. He shot only 21.7 percent from the field, receiving a wild 5.8 shots per game in just 11.5 minutes; his per-36 average would have been 18 shot attempts per game. He generated -0.3 win shares during his tenure, a phenomenal feat for such a short time. Woodson was easily waived, but his status as perhaps the worst pure free agent ever signed is enough to place him on this list.