15 free agent (and trade) near-misses that would've changed Yankees history
Bernie Williams Nearly Bolts for Red Sox, 1998-99
The Yankees of the '90s would've been more than just a nice little historical footnote even if Bernie Williams had left after the 1998 season. They would've just set an all-time wins mark, after all. The narratives would've been juicy. "Can this dynasty keep itself together without its calming glue in Williams?"
The potential intrigue lost doesn't balance out how harrowing it is to think of Williams on the Red Sox in 1999, 2000 and 2001, though. And that's exactly what would've happened if the Yankees' front office hadn't bent to his will.
Williams entered the 1998-99 offseason reportedly wanting to remain a Yankee, but the Sox offered him seven years and $91.5 million, while New York offered just five years and $60 million. That's good business. If Boston had been able to pull off this coup, neuter the Yankees and flex their financial muscle, they could've reversed the curse five years earlier and muzzled New York in the midst of a budding dynasty. It would've been brutal.
Thankfully, the Yankees upped their offer to $89.7 million for seven years, though it didn't come before another twist of fate. Joe Torre wanted to swing for the fences and grab the moody Albert Belle, who was all set to accept that five-year, $60 million offer ... before he backed out and chose Baltimore instead. If not for Belle being a fickle weirdo, the Yankees would've added his worst years to their payroll while watching Williams pepper the Monster -- and, oh yeah, the Yanks and Sox locked horns in the ALCS that fall.