5 Worst signings in Milwaukee Bucks history

Tim Thomas, Milwaukee Bucks (Photo by: Ezra Shaw/Getty Images)
Tim Thomas, Milwaukee Bucks (Photo by: Ezra Shaw/Getty Images) /
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Milwaukee Bucks basketball
Milwaukee Bucks basketball (Photo by Patrick McDermott/Getty Images) /

3. Bobby Simmons

In a story that is beginning to sound familiar, the Milwaukee Bucks signed Bobby Simmons after he had a career year and then quickly fell into buyer’s remorse. After a few quiet years in Washington and with the Clippers, Simmons finally broke out during the 2004-05 season, starting 74 games for the Clippers, averaging 16 points per game on 44 percent shooting from deep. He won the NBA’s Most Improved Player award the year before hitting free agency.

That summer, the Bucks signed Simmons to a 5-year, $47 million dollar deal in the hopes that they could get a budding star for under $10 million a year. If it had played out that way it would have been a steal. But, sadly, Simmons could never recapture the spark he had in Los Angeles. Maybe it was the change in climate that did it or maybe he just wasn’t that good to begin with.

His first season in Milwaukee was decent albeit unimpressive. He averaged 13 points per game and shot 42 percent from deep, but that didn’t translate to much success for Milwaukee. They’d ultimately make the playoffs before losing in the first round to the powerhouse Detroit Pistons.

After one mildly successful season, things went really bad for Simmons. He’d miss the entirety of the 2006-07 season with an ankle injury and was never the same player after he returned. He played just one more underwhelming season with Milwaukee before being traded to New Jersey with fellow disappointment Yi Jianlian.