When Bernie Williams nearly left New York

October 12, 1999 — For the first time since Bucky Dent carved himself a place in playoff lore, the Yankees and Red Sox are gearing up to meet in the postseason. Boston is all abuzz as the AL East Champions are playing host to the Wild Card team and defending World Champions from New York. While the Yankees finished with 98 wins this season, the Red Sox’s 104 victories were tops in the Majors, and the Yanks will have to hope that their superior pitching can overcome a power-packed Boston lineup.

Ironic in this meeting is one center fielder for the Red Sox, the former Yankee Bernie Williams. Williams, after becoming a Yankee mainstay, left the Bronx after the Yankees’ 125-win season last year. While the Yankees were prepared to offer Williams a five-year, $60-million contract, the star and his agent Scott Boras rejected that deal. They knew they could get more elsewhere and were tired of playing games with George Steinbrenner.

So now Williams will face off against his old team in Fenway. The Yanks — with their tempestuous twosome of Paul O’Neill and Albert Belle — look strong, but can they overcome the Red Sox?

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We know that didn’t happen. Bernie Williams wasn’t on the Red Sox in 1999, and the Yankees were the AL East champs again.

But it was close. For a while in 1998, it looked like Bernie was Boston-bound, and if he had landed in Fenway, it’s not hard to imagine the Sox taking the division. Williams was the top offensive center fielder in the AL in 1999. His VORP that year — a measure of how much better he was than the next best available option — was 79.9. Darren Lewis, the Red Sox’s starting center fielder, pulled down a -24.8 VORP. That swing of 100 would have theoretically netted the Sox 10 more wins and a spot atop the AL East. It’s funny how history turns out.

“Bernie on the Red Sox?” you might say with a chuckle. “That never would have happened, right?” While it can be tough to see through Scott Boras’ hyperbole and fake seven-year offers, by all accounts in November of 1998, Bernie Williams nearly ended up in Fenway.

Bernie’s tale begins in 1997 when the Yankees were trying to extend their center fielder. They offered him a five-year deal worth just south of $40 million. As you could guess, they were laughed out of the room, and for a while, it seemed as though their offer and past contract snubs were insulting enough to convince Williams to cease negotiations entirely. Money and loyalty are powerful motivators.

Throughout November, Scott Boras and the Yankees engaged in their usual dance as reports of other deals surfaced. At various times, the Diamondbacks, Dodgers, Rockies and Red Sox all expressed interest in Williams. But by the end, it became a battle between rivals. The Yankees and the Red Sox squared off with a big x-factor waiting in the wings.

To the dismay of Yankee fans, that x-factor was none other than hotheaded slugger Albert Belle. As the Yankees and Bernie looked to finalize their looming divorce, a new marriage between the Yankees and Belle was on the horizon. While the Yanks were initially interested in Jim Edmonds, those talks fizzled, and at 32 years old, Belle was one of the most sought-after free agents of 1998. The hip condition that would end his career two seasons later was nowhere to be found, and his numbers and temper were fearsome.

When Williams rejected that five-year, $60-million deal, the Yankees turned their attention to Belle. When I left my apartment on Wednesday night, November 25, 1998, to attend a friend’s Thanksgiving Eve party, I believed that Bernie Williams’ tenure in the Bronx was over. The Yanks and Bernie, as Buster Olney had reported that morning, were nearing a final separation, and Bernie was about to land in Boston.

The Yankees however had an out: Scott Boras offered them one last chance to match the Red Sox’s supposed seven-year, $90-million deal. Bernie, it seemed, wasn’t as keen to get out of New York as earlier reports indicated. When I got home late that night, my dad had left me a note on the door: Bernie Williams signs with the Yanks for seven years and $87.5 million, it said. I was ecstatic. Somehow, the Yankees and Bernie were able to overcome their differences, and Bernie would remain a Yankee.

In the end, it was always tough to tell if Bernie was actually going to leave. Three columnists in The Times — Jack Curry, Harvey Araton and Buster Olney — all speculated that Boras used vague, half-serious offers to get the Yanks to ante up. By keeping the archrival Red Sox involved, Boras knew the Yanks would pay, and he won.

When the real 1999 ALCS dawned, the Yanks, led by Bernie, beat the Red Sox with their sad excuse for a center fielder. As we know, Bernie’s Yanks would go on to great success. While Bernie’s contract became something of an albatross by the end of it and Williams still seems to have a poor relationship with the Yankees, keeping Bernie out of Boston was a sage move.