2. Doug Strange 1998
Doug Strange might seem like a…strange number two worst free agent in team history, but he was really, really bad. Following the Freak Show 1997 season where the Pirates went 79-83 and were in contention for most of the season, the team signed Strange to a two-year, $1.12 million contract.
That doesn’t sound like a lot of money until you realize the 1998 Pirates had a $12 million payroll, meaning Strange’s $575,000 was quite a hefty sum for such a terrible player. He was released mid-season, but the team had to pay him, so his $550,000 contract remained on the books for the 1999 season as well.
In 90 games for the Pirates, Strange hit .173/.217/.216/.433, had an astonishing OPS+ of 14 and was worth -2.0 WAR. The WAR is the most impressive aspect to how terrible Strange was. In a little over half a season, he cost the team two wins on his own. When you couple that with taking up nearly 5 percent of the overall payroll, you got yourself a pretty terrible free agent.
Strange, however, is not the worst free agent in Pirates’ history, but he may be the least known bad free agent. Our number one pick will forever live in bad free agent infamy…
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