8. Andy Hawkins: Three Years, $3.6 Million, 1988
Whenever the Yankees massively outbid the competition (even by 1980s free agency standards) to secure their chosen target, it typically doesn't go well.
Fingers crossed for the back end of the Gerrit Cole deal.
Back in 1988, the Yanks placed undue pressure on Hawkins, a former San Diego Padres standout, outbidding the field by $1.6 million to secure the right-hander. Manager Dallas Green called Hawkins the rotation's "anchor" before the season began -- which made sense, ultimately, because he dragged the whole operation down.
Hawkins went 15-15 in 1989 for a bleak Yankee team, but posted a 4.80 ERA and led the American League with 111 earned runs allowed. The next season, he flatlined, posting an 8.56 ERA through early May, which earned him his release ... a decision the team backtracked on when a fellow starting pitcher came up lame later than evening. Hawkins' second chance at life in the Bronx ended up allowing him to throw a no-hitter and lose -- and not by a 1-0 score, either. This fellow lost a no-no 4-0, thanks to a fleet of errors behind him and five walks.
A memorable legacy. A bad signing.