6) NY Mets worst free agent signing: Luis Castillo
Mets fans remember Luis Castillo for one moment. With two outs in the Bronx, he dropped a routine pop up to allow the New York Yankees to win the game. It became one of the most notorious errors in club history. It may be the worst in a regular season game, too.
Castillo is like a couple of other guys on this list. He first joined the Mets through a trade. Acquired in mid-2007 from the Minnesota Twins, he actually hit well for the Mets in his first 50 games that season. The light-hitting second baseman batted .296/.371/.372.
Unfortunately, it wasn’t just a rental. Castillo re-signed with the Mets in the offseason. The deal was a $25 million contract for four years. Like so many bad free agent signings in Mets history, injuries and a bad performance when healthy wrecked the deal.
Castillo played in 87 games in 2008 while batting .245/.355/.305. It was a poor start made worse by the way the team collapsed for the second straight year.
Somewhat quietly, Castillo returned to play in 142 games in 2009 and produce at the level we should have expected him to. He hit .302/.387/.346. Unfortunately, he was back to hitting .235/.337/.267 in only 86 games the following year. The Mets ended up releasing him in spring of 2011 before the final year of his contract was through.