Top Five Worst Free Agent Deals in Pittsburgh Pirates History

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Yesterday, we tackled the top five best free agent deals in Pittsburgh Pirates’ history. Today, we turn to the five worst.


The Pittsburgh Pirates had 20 consecutive losing seasons and that doesn’t happen by accident. A combination of bad drafting, bad developing, bad managing, and bad play doomed the Pirates to this fate. There was also some bad general managing from Cam Bonifay and Dave Littlefield.

Littlefield and Bonifay gave many players some bad contracts during their contributions to the losing streak and you could probably do a top 100 list of worst moves by these two men, but today, to balance out my top five best free agent signings in Pirates’ history list, I am going to cover my picks for the top five worst free agent signings in Pirates’ history.


5. Joe Randa 2006

Joe Randa is an interesting player because you could probably also include him on the list of best Pirates’ acquisitions for his tremendous 1997 season with the Pirates. A lot changed in a decade, mostly because Joe Randa was a decade older and his baseball career was on the decline.

His numbers on the surface weren’t completely atrocious. He batted .267/.316/.388/.704, had an OPS+ of 81 and was worth -1.0 WAR. Those numbers are bad, but really they’re par for the course for the early-to-mid 2000s Pirates’ teams. What makes Joe Randa such a terrible free agent? How about he blocked eventual NL batting champion Freddy Sanchez from getting regular playing time.

The fact that the Pirates had a player the caliber of Freddy Sanchez in the wings and chose to pay Joe Randa $4 million to block a young player on his rookie deal making just $340,000 is mind boggling. Joe Randa was living proof of Dave Littlefield’s commitment to simply trying to get win 81. He didn’t care about building a playoff team, he simply wanted to get enough pieces to end the streak. He never broke it all up and started over. He just tried to stop gap his way to success and obviously it failed massively.


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