15 worst New York Yankees free agent signings in franchise history

Minnesota Twins v New York Yankees
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5. Kenny Rogers: Four Years, $19.5 Million, 1995

Kenny Rogers was the original Joey Gallo, and The Gambler certainly gambled away his role as the highest-paid member of the Yankees' staff very quickly.

Despite concerns, at the time, that Rogers wasn't a fit in New York, George Steinbrenner presented the counterargument, "Na na na NA NA, I CAN'T HEAR YOU!" He signed Rogers to a nearly $20 million deal the same offseason he added Cone, and by Year 2, he was looking for any way possible to wriggle out of it.

Rogers was a perfectly competent starter (competent-to-good!) everywhere else he ever resided throughout his career, eventually dominating the Yankees in the 2006 ALDS with the Tigers as a 41-year-old man (aided by a handful of goop). That places him in the worst category of failed Yankees free agent signings: arrives, sucks, gets aggrieved about something, takes his own sucking out on the organization at a later date. What are you so mad about? You were the one who sucked!

The Yankees won the 1996 World Series, but no thanks to Rogers, who posted a 9.00 ERA in two innings in the ALDS, 12.00 ERA in three innings in the ALCS, and 22.50 ERA in two innings in the World Series. They basically took him out of the mix, and he still managed to unwrap all the Christmas presents early and poop in the sink.

By summer 1997, the Yankees were eating chunks of Rogers' contract to send him to Oakland. It was that day that he vowed revenge for ... getting him out of a bad situation? Whatever. Dudes, am I right?