Yankees worst free agent contracts ever handed out

SAN DIEGO, CALIFORNIA - JULY 3: Jacoby Ellsbury #22 of the New York Yankees slides as he scores during the ninth inning of a baseball game against the San Diego Padres at PETCO Park on July 3, 2016 in San Diego, California. (Photo by Denis Poroy/Getty Images)
SAN DIEGO, CALIFORNIA - JULY 3: Jacoby Ellsbury #22 of the New York Yankees slides as he scores during the ninth inning of a baseball game against the San Diego Padres at PETCO Park on July 3, 2016 in San Diego, California. (Photo by Denis Poroy/Getty Images) /
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(Photo by Jim McIsaac/Getty Images)
(Photo by Jim McIsaac/Getty Images) /

Roger Clemens

When Clemens addressed the Yankee crowd up from the comforts of George Steinbrenner’s box in May of 2007, fans knew Clemens’ second term would soon begin. He was coming off yet another abnormally brilliant year for a guy his age (44-years-old), pitching to a 7-6  record with a sparkling 2.30 ERA with a 1.04 WHIP in his last year with the Astros.

This did, however, come with the fact that he didn’t even play the full season and averaged just under six innings per start. However, the armor was beginning to rust a bit. But the Yankee brass felt he would bolster a pitching core littered with free-agent mistakes I’ll go over later.

Clemens was given a pricey 1-year, $18.7 million contract with all sorts of special treatment, such as a family clause that stated he could skip road trips if he weren’t scheduled to pitch and allowed him to leave the team in between starts to be with his family.

He had an otherwise mediocre year, posting a 6-6 record with a 4.18 ERA in 17 starts. He was at least able to earn his 350th win, cementing him as one of only three pitchers to solely pitch in the live-ball era and reach 350 victories. But besides that accolade, it was a very forgettable end to the Rocket’s career.