Worst free agent signing in Milwaukee Bucks history: Bobby Simmons
5 years, $47 million
Coming out of DePaul University, swingman Bobby Simmons was not heralded or chased-after, with the Washington Wizards taking him No. 43 overall in the 2001 NBA Draft.
After two nondescript seasons in Washington and one with the Los Angeles Clippers, he blew up for the Clippers to the tune of 16.4 points per game in his fourth NBA season.
That summer he hit free agency, and the Milwaukee Bucks valued him as the player he was in his fourth season. They gave him a large contract, five years and $47 million. He promptly began failing to hold up his end of the bargain.
In his first season with the Bucks, he was a middling scorer and little else, scoring 13.4 points per game, while his efficiency and box score stats all declined. Then he suffered a serious ankle injury that kept him out for the entire 2006-07 NBA season.
By the end of his time in Milwaukee, Simmons had done little-to-nothing to earn his contract, getting worse and worse each year. In 2008, he was traded to the then-New Jersey Nets in a package for Richard Jefferson, the close of his time with the Bucks.