NBA free agency: 30 worst free agent signings in NBA history

Gilbert Arenas, Nick Young, Washington Wizards. (Photo by David Dow/NBAE via Getty Images)
Gilbert Arenas, Nick Young, Washington Wizards. (Photo by David Dow/NBAE via Getty Images) /
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Bobby Simmons, Milwaukee Bucks
Bobby Simmons, Milwaukee Bucks. (Photo by Gary Dineen/NBAE via Getty Images) /

Bobby Simmons. 22. player. 89. . Milwaukee Bucks. 5 Years, $47 Million

Worst free agency signings in NBA history: 22. Bobby Simmons, Milwaukee Bucks

Bobby Simmons found himself in an interesting position after the 2004-05 NBA season with the Los Angeles Clippers. He posted 16.4 points, 5.9 rebounds, 2.7 assists and 1.4 steals per game on the final year of his deal and he emerged as the NBA’s Most Improved Player that season.

In the 2005 NBA free agency market, the Milwaukee Bucks came calling following his breakout year with the Clippers. He signed a five-year, $47 million deal and was believed to be a centerpiece for the franchise with his size and ability at 6-foot-8 and 210 pounds.

His first season in though, his production dropped to 13.4 points, 4.4 points, 2.3 assists and 1.1 steals per contest, though he still managed to shoot 42 percent from 3-point range. The Bucks went 40-42 and squeaked into the 2006 NBA Playoffs, but it was clear Simmons may have reached his peak.

The following season, Simmons missed all 82 games in their entirety due to a broken ankle. When he returned in 2007-08, it was clear he wasn’t himself. He put up 7.6 points, 3.2 rebounds and 1.1 assists per game through 70 appearances in his return. However following that season, he was traded to the then-New Jersey Nets with Yi Jianlian for Richard Jefferson.

Once his deal ran out with the Nets, he appeared in two games with the San Antonio Spurs (2010-11) and 28 with the Los Angeles Clippers (2011-12) before finding himself out of the league by 2012.