13. Bernie Williams, 1998: Seven Years, $87.5 Million
Yes, the Yankees almost lost Bernie Williams to the Red Sox back in 1998-99 before relenting to their center fielder's demands and keeping the band together. That was a wise move!
Williams delivered, upping his league-leading .339 average to .342 the next season, a year that coincidentally featured the Yankees and Red Sox facing off in the ALDS.
Bernie Went Boom to set the tone in that series, delivering a walk-off home run off Rod Beck in Game 1 at Yankee Stadium that never would've happened if Steinbrenner hadn't ponied up over the previous winter.
For an accomplished guitarist, it was one hell of a solo ... shot.