Bernie Williams nearly left the Yankees after the 1998 season, despite being a core piece of their dynasty. The five-time All-Star and four-time World Series champion had to personally plead his case to owner George Steinbrenner after New York hesitated to re-sign him, ultimately securing a seven-year, $87.5 million deal that kept him in the Bronx.

Bernie Williams had to ‘plead his case’ to Stay with Yankees

Williams recently reflected on the contract saga during an appearance on Diggin’ Deep with Eric Hosmer. He recalled how the negotiations were more cutthroat than he had expected, leading to a difficult period of uncertainty.

“I grew to understand that these guys have my best interest … but that was just a fallacy,” Williams said. “At the time, it was very difficult because I think you were kind of expected to take what they call the hometown discount and try to sign for less money.

“It was just a purely transactional situation, and it became very acrimonious because I thought that I was owed something, and the team said, ‘We paid you, man.’”

By then, Williams had spent 13 years in the Yankees’ organization, including eight seasons in the majors. He was coming off the best year of his career in 1998, leading the American League with a .339 batting average while posting a 160 OPS+. He also hit 26 home runs, drove in 97 runs, and finished with a .997 OPS.

His performance attracted interest from other teams, most notably the Red Sox, who offered him a seven-year, $91.5 million contract. Meanwhile, the Yankees were considering Albert Belle as a possible replacement and had only put a five-year, $60 million offer on the table.

The call that changed everything

Williams’ agent, Scott Boras, told him there was only one way to get the Yankees to reconsider their stance—he needed to go straight to Steinbrenner. Boras knew the Yankees wouldn’t change their offer unless Williams made a personal appeal, so he gave him direct instructions.

“Call him at his house and plead your case,” Williams recalled Boras saying. The idea of calling Steinbrenner at home was bold, but Williams had little choice. He was facing the real possibility of leaving the Yankees, and this was his last shot at getting the deal he wanted.

So, he did. At the time, Williams was in Puerto Rico, weighing his options as the Red Sox’s lucrative offer loomed. He picked up the phone and dialed Steinbrenner’s home. To his surprise, it was Steinbrenner’s wife who answered.

“Hey, Bernie, how you doing?” she asked, recognizing his voice immediately.

Williams didn’t waste time. “Mrs. Steinbrenner, this is Bernie Williams. Sorry about imposing, but I need to talk to your husband about some business.”

A few moments later, Steinbrenner came on the line. His voice was direct and to the point. “What do you want?” he asked.

Williams didn’t hesitate. He had to make his case as clearly as possible. He needed a deal that matched what other star players were getting. “I want Piazza’s money,” he said, referencing Mike Piazza’s seven-year, $91 million contract with the Mets.

Steinbrenner didn’t give him an immediate answer. Instead, he told Williams to wait. The Yankees needed to run the numbers. For Williams, the next hour felt like an eternity. He had put everything on the line with that call, and now all he could do was wait for Steinbrenner’s decision.

Finally, the phone rang again. It was Steinbrenner. The Yankees had crunched the numbers and were ready to make a better offer. Instead of the five-year, $60 million deal they had originally proposed, they were now willing to go to seven years and $87.5 million—just shy of the Red Sox’s offer.

Boras advised Williams to take the deal. “This is the best offer you’re going to get. If you want to remain a Yankee, you go ahead and take that.”

Williams accepted, securing his place in the Bronx for the next seven seasons. He would go on to help the Yankees win two more championships and cement his legacy as one of the most accomplished players in franchise history. By the time he retired, he ranked among the team’s all-time leaders in hits (2,336, fifth), home runs (287, eighth), RBIs (1,257, seventh), and batting average (.297).

Be that as it may, one phone call had saved his Yankees legacy.

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