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By Hayden Bird
Wade Boggs shed light on some Red Sox-Yankees history: In late 1992, Wade Boggs opted to swap his Red Sox uniform for Yankee pinstripes as a free agent. It was, from a Boston standpoint, an infamous turnabout from a future Hall of Famer.
Boggs, who went on to win the lone World Series of his career while a member of the Yankees in 1996, recently offered some new details on the backstory behind his decision to exit Boston for New York. He spoke to MLB Network’s Jon Morosi on “The Road to Cooperstown” podcast during Hall of Fame weekend in July.
According to Boggs, Jean Yawkey promised him that he would get a new contract at the end of the 1991 season and “follow in the same footsteps as Carl [Yastrzemski] and Ted [Williams],” playing their entire careers in Boston. The terms he recalled were for $37 million over seven years.
Boggs explained that he was so adamant to sign at that point that he even offered to sign the deal on a napkin.
“I’ll sign a napkin right now,” Boggs said. “And [Yawkey] says, ‘Don’t worry about it, Lou [Gorman] and John [Harrington] will get it done.”
Shortly afterward in Feb. 1992, Yawkey passed away at the age of 83. Following her death, Boggs said that Boston management “took the offer off the table.”
As a result, he eventually became a free agent following the ’92 season.
“The next morning, the Yankees called,” Boggs recounted, saying that a meeting was set up at a hotel owned by then-Yankees owner George Steinbrenner. New York general manager Joe Molloy was present, though Steinbrenner was still serving a ban from day-to-day operations of the team after paying gambler Howard Spira to dig up dirt on outfielder Dave Winfield.
“We sit down and have a conversation and we’re talking and Joe Molloy goes, ‘Would three years and $11 million put you in Pinstripes?’ I said, ‘I need to go discuss it with my wife.’ And I ran out to my Porsche and said, ‘Honey, we’re going to New York.’”
Boggs added one more humorous tidbit.
“There’s a gentleman sitting at a table over here reading a newspaper,” he said of the hotel meeting. “The newspaper comes down and it’s George, and he winks at me.”
“That is something out of a movie,” Morosi joked during an interview on MLB Network as he discussed the conversation with Boggs. Steinbrenner would eventually be reinstated prior to the 1993 season.
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
Trivia: As a minor leaguer in 1981, Wade Boggs played in the longest professional baseball game ever (which lasted 33 innings, spanning three days). Can you name the other future Hall of Famer who also played in that game?
(Answer at the bottom.)
Hint: The game was played between the Pawtucket Red Sox and the Rochester Red Wings. The Red Wings were at that point an Orioles minor league affiliate.
Scores and schedules:
The Red Sox begin a pivotal four-game series against the Yankees in New York tonight at 7:15 p.m.
The Patriots will also be on the road for the preseason finale against the Giants at 8 p.m.
On Saturday, the Revolution play the Crew in Columbus at 7:30 p.m.
More from Boston.com:
Connecticut makes to the U.S. championship: The Connecticut representative (from Fairfield) at the Little League World Series defeated Nevada on Wednesday to advance to the U.S. Championship.
CONNECTICUT WILL PLAY FOR THE LLWS U.S. CHAMPIONSHIP 🏆 pic.twitter.com/2qSDrTLwDc
— SportsCenter (@SportsCenter) August 20, 2025
“Come on, Dwyane”: Patriots players tried their hand(s) at catching a solo cup in another solo cup.
They were so locked in 😂@DraftKings | #NEPats pic.twitter.com/pfBakq9di4
— New England Patriots (@Patriots) August 20, 2025
On this day: In 1984, rookie Roger Clemens struck out 15 in a complete game gem as the Red Sox crushed the Royals 11-1.

Daily highlight: An outstanding tag at the plate from Wednesday’s Little League World Series action.
Unreal tag at the plate 😤 pic.twitter.com/ZhsLPL1Q5K
— ESPN (@espn) August 20, 2025
Trivia answer: Cal Ripken Jr.
Hayden Bird is a sports staff writer for Boston.com, where he has worked since 2016. He covers all things sports in New England.
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