The biggest rivalry in baseball certainly is between the Boston Red Sox and the New York Yankees.
There are obviously some other big rivalries out there, but none compare to Boston and New York even to this day. The reason for this isn't even necessarily the product on the field right now in the year 2025. But, the history between each matchup. If you follow either the Red Sox or the Yankees, you likely know all about this history. You likely know all about Babe Ruth and the years of Yankees success and the Boston heartbreak. The Red Sox turned it around starting in 2004 after the rough end to the 2003 playoffs and from there, things have been in Boston's favor.
There's a lot of history there and over the course of it all, we've seen some notable players change hands. There have been plenty of guys who have worn both of the historic jerseys and one of the biggest in recent memory was Hall of Famer Wade Boggs. He spent the first 11 years of his career in Boston and then the next five years of his career in New York. He's seen the rivalry from both sides and shared with MLB Network's Jon Morosi what led to his switch on "The Road To Cooperstown" podcast.
"At the end of the (1992 season) they didn't pick up my arbitration rights which made me a free agent," Boggs said. "First team to call was the (Los Angeles Dodgers). Tommy Lasorda wanted me to come play for the Dodgers. I didn't want to change teams and I didn't want to go to the West Coast. I didn't want to change leagues and go to the West Coast...So I respectfully declined the Dodgers' offer. The next morning, the Yankees called...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 noted that initially he didn't want to leave Boston and spoke with Jean Yawkey before her death and she wanted to keep him in Boston forever. After she passed, the discussions with the team changed before the 1992 season. You can check out the whole story here. It's fascinating to hear from someone speak from both sides of the aisle.
More must-reads:
Get the latest news and rumors, customized to your favorite sports and teams. Emailed daily. Always free!