Hall Of Famer Reveals Why He Left Red Sox For Yankees Mid-Career

Plenty of MLB legends have spent time on both sides of the Boston Red Sox-New York Yankees rivalry, dating all the way back to Babe Ruth. While the two teams rarely trade with each other, they often fight over the same players and try to steal each other’s stars whenever they can.

One famous example of that happened with Wade Boggs — one of the greatest hitters in MLB history. The first-ballot Hall of Famer amassed 3,010 hits and batted .328 — the highest career average of any living player — over 18 seasons from 1982 to 1999.

Boggs spent the first 11 of those years with the Red Sox, where he enjoyed his best seasons. The legendary third baseman won all five of his career batting titles with Boston, batting .338 during his time there.

After failing to win a World Series with the Red Sox, however, he signed with the Yankees after the 1992 season and spent five years in pinstripes, helping New York win a championship in 1996.

On Jon Morosi’s “The Road To Cooperstown” podcast, Boggs revealed why he left Boston for the team’s biggest rival.

The tale of Wade Boggs’ departure from the ⁦@RedSox⁩ to the ⁦@Yankees⁩ completely shocked me — right down to the final reveal of the person listening in on the negotiations. ⁦@MLBNetwork⁩ ⁦@MLBNetworkRadio⁩ ⁦@baseballhall⁩ ⁦@ChickenMan3010⁩ pic.twitter.com/RvSo5wBEt3

— Jon Morosi (@jonmorosi) August 20, 2025

Boggs explained that the Red Sox’s previous owner, Jean Yawkey, offered him an unofficial seven-year, $37 million contract after the 1991 season, which Boggs accepted. Yawkey passed away during the offseason, however, and Boston’s front office took the offer off the table.

Boggs endured the worst year of his career in 1992, batting .259/.353/.358 at age 34. Believing he was in decline, the Red Sox didn’t pick up his arbitration rights, allowing him to become a free agent.

The Yankees, driven by George Steinbrenner’s insatiable thirst for stars, promptly swooped in, signing him to a three-year, $11 million deal.

It turned out to be a great move for New York, as Boggs immediately bounced back and made four straight All-Star teams for the Yankees.

Boston didn’t learn its lesson, either, allowing a similar saga to play out with Boggs’ former teammate, Roger Clemens, a few years later.

While Boggs accomplished a lot during his decade-plus with the Red Sox, it would have been nice if he’d finished his career in Boston as Yawkey intended.