Last Updated: June 17th, 2026 by Matthew Brown
Baseball’s history is written in box scores and record books, but its most fascinating chapters are the ones that almost happened. Behind closed doors and in late-night phone calls, some of the game’s biggest stars nearly switched uniforms in ways that would have completely rewritten baseball’s story. Here are twelve trades that came whisper-close to changing everything we know about America’s pastime.
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Randy Johnson to Toronto: The Big Unit’s Canadian What-If
In 1998, the Blue Jays were tantalizingly close to landing Randy Johnson from the Mariners. The deal would have sent young pitcher Roy Halladay and two prospects to Seattle for the Big Unit. Toronto’s front office hesitated at the last moment, concerned about Johnson’s impending free agency. Instead of watching Johnson dominate in the SkyDome, Blue Jays fans had to watch him as an opponent.
How Tom Glavine Almost Became an Expo in 1990
Before becoming a Braves legend, Tom Glavine was nearly shipped to Montreal for Tim Raines and Dennis Martinez. The deal fell apart when Braves GM Bobby Cox, who had just moved from the dugout to the front office, insisted on keeping the young lefty despite his 7-17 record in 1988. That decision helped build Atlanta’s dynasty of the 1990s, while Montreal fans were left wondering what might have been.
A-Rod to Boston: The $252 Million Deal That Died
In December 2003, the Red Sox had a deal in place to acquire Alex Rodriguez from the Rangers for Manny Ramirez and a young Jon Lester. The Players Association rejected A-Rod’s voluntary salary reduction, killing the deal. Weeks later, Rodriguez landed with the Yankees instead, forever altering the AL East rivalry and the narrative of the 2004 season’s curse-breaking year.
Mariano Rivera for Felix Fermin: The Yankees’ Near Miss
In spring training 1996, the Yankees nearly traded an unproven Mariano Rivera to the Mariners for light-hitting shortstop Felix Fermin. Gene Michael and Buck Showalter convinced George Steinbrenner to give the young Rivera a chance instead. That decision led to five World Series titles and the greatest closer in baseball history.
Barry Bonds Almost Made Atlanta Even More Dominant
Before the 1992 season, the Braves nearly acquired Barry Bonds from the Pirates for a package centered around young outfielder David Justice. The Pirates backed out at the last minute, and Bonds signed with San Francisco the following year. Imagine those dominant Braves teams of the ’90s with Bonds in the lineup alongside Chipper Jones.
The Mets Almost Had Ken Griffey Jr. in His Prime
In 1999, the Mets were inches away from landing Ken Griffey Jr. from Seattle. The deal would have sent Armando Benitez, Roger Cedeno, and top prospect Octavio Dotel to the Mariners. Junior exercised his no-trade clause, eventually landing in Cincinnati instead, while Mets fans were left dreaming of The Kid patrolling center field at Shea Stadium.
George Brett to the Reds: The Trade That Made Cincinnati Cry
In 1979, the Reds and Royals had agreed in principle to swap George Brett for Tom Seaver. Reds owner Dick Wagner got cold feet at the last moment, fearing the backlash of trading the popular Seaver. The decision kept Brett in Kansas City for his entire Hall of Fame career, while Cincinnati fans were left to wonder what might have been.
Pedro Martinez’s Near-Journey to the Bronx
Before the 1998 season, the Yankees nearly acquired Pedro Martinez from the Expos. The proposed deal would have sent top prospects to Montreal, but George Steinbrenner hesitated over Pedro’s size and durability. Martinez went to Boston instead, where he dominated the Yankees for years and became a Red Sox legend.
Angels Nearly Landed Miguel Cabrera Before Detroit’s Dynasty
In 2007, the Angels were the frontrunners to land Miguel Cabrera from the Marlins, offering a package centered around Howie Kendrick and Ervin Santana. The Tigers swooped in at the last minute with a better offer, changing the course of both franchises. Imagine Cabrera protecting Vladimir Guerrero in that Angels lineup instead of anchoring Detroit’s powerhouse teams.
Yankees Almost Sent Rickey Henderson to the Giants in ’88
The Yankees nearly dealt Rickey Henderson to the Giants for Will Clark and two prospects in 1988. The deal would have paired Henderson with a young Matt Williams in San Francisco’s lineup. Instead, Henderson stayed in New York before eventually returning to Oakland, where he would help the A’s beat the Giants in the World Series in 1989.
Montreal’s Missing Moment: Pujols Almost Became an Expo
In 2000, the Expos had a deal in place to acquire minor leaguer Albert Pujols from the Cardinals for pitcher Dustin Hermanson. Cardinals GM Walt Jocketty pulled back at the last minute, keeping the future Hall of Famer in St. Louis. One can only wonder if having Pujols might have saved baseball in Montreal.
The Midnight Handshake: Yankees and Sox Almost Swapped DiMaggio and Williams
It happened at Toots Shor’s restaurant in Manhattan after more than a few drinks – Yankees owner Dan Topping and Red Sox owner Tom Yawkey shook hands on what would have been baseball’s biggest blockbuster ever. The straight-up swap of Joe DiMaggio for Ted Williams was agreed to that night in 1947, only to fall apart in the sobering light of day. The Yankees-Red Sox rivalry might have played out very differently if that handshake had turned into signatures on paper.