Nothing is a bigger “what if” in baseball than the trade. Unlike other sports, a trade can truly make or break a team in baseball and fans from both sides are left wondering what would have happened if such a deal hadn’t gone down. Cubs fans maintain that giving Lou Brock to the Cardinals was one of the worst moves in team history. Orioles fans know that the trade for Frank Robinson was key to Baltimore winning four pennant and two World championships. So many times, a simple swap of players turns one team into legends and another into losers. It’s what makes it so tricky as more than a few general managers have made swaps they regret big time.
However, it’s often ignored the trades that were going to happen but didn’t. They fall through over money, over egos or other issues and often forgotten about. But these almost-trades end up being just as big, if not bigger, than the ones that did happen. They involve players who became stars and who helped their teams to titles which might not have been had they been swapped. There’s also teams that missed the boats on big names that could have helped them majorly. For every huge deal that happens there’s another that came close and the potential for transforming a team is huge. Here are 20 huge MLB trades fans didn’t know nearly happened and how they could have shifted some careers majorly.
20 Jose Bautista for Domonic Brown
You’re going to be seeing the Blue Jays on this list a few times for trades they missed out on somehow. But here’s a notable case of a trade that was actually better for them not going through with it.
Jose Bautista was easily the star of Toronto at the time, a six time All-Star who led the league twice in home runs.
So word of Toronto wanting to drop him in 2013 rocked the fanbase. The deal would have sent Jose to the Phillies for rookie Domonic Brown. Probably the reason it never went through was the sheer outrage of Toronto fans at letting Jose go. Bautista spent a few more years before Toronto finally cut him, yet fans were happier him being there than just traded off.
19 Zack Greinke to the Nationals
Had this deal gone through, it would have prevented the trade that ended up helping the Royals much better down the road. Zack Grienke was a good pitcher for Kansas City but he made it known he’d be heading to free agency in 2012. So the Royals tried to get some return to him by offering him to the Nationals for names like Drew Storen, Danny Espinosa, and Jordan Zimmermann. But Greinke himself nixed the trade, not wanting to go to Washington.
So instead, he was sent to the Brewers for Lorenzo Cain and Alcides Escobar, a move many cite as the key to the Royals becoming 2015 World champions. Amazing to think how Greinke’s disdain of Washington caused such a shift.
18 Derek Jeter to the Expos
Even by the Expos’ standards, this one has to hurt. By 1999, Derek Jeter was proving himself a true star, having just won his third World Series with the Yankees and a great shortstop. Montreal Expos owner Jeffrey Loria became obsessed with getting Jeter, telling GM Jim Beattie to do whatever it took. That included trading Vladimir Guerrero and a big wad of cash.
However, no matter how enticing, the Yankees were smart enough to know keeping Jeter was the best move. It’s probably a good thing the Expos didn’t have to deal with a foolish owner/GM in New York or Jeter would have lost out on a couple more titles and a few MVP awards.
17 Ken Griffey Jr. to the Mets
While he never got a World Series win, Ken Griffey Jr. is easily recognized as one of the best sluggers of his time. He led the league in homers three straight seasons, a 13-time All-Star, seven time Silver Slugger win, 10 Golden Gloves and the Hall of Fame. He had success in various teams like Seattle and Cincinnati yet the Mets tried to get him.
In 1999, the Mets were making a big move to get Griffey and various players like Armando Benitez, Jay Payton, Octavio Dotel and Roger Cedeno were all mentioned.
It seemed ready to go but, with just 15 minutes to decide, Griffey chose not to go to New York. Mets fans might hold that Griffey and Mike Piazza could have been a fantastic unit but they settled for joining the Hall of Fame together.
16 Manny Ramirez to the Mets
Boston fans know Manny Ramirez as the part of the team that finally broke “The Curse” in 2004. He’d played for several teams in his career but it was Boston where Ramirez shined, winning two World Series and a popular guy. Yet, it could have been only one had this deal gone through.
Right after Ramirez became the 2004 Series MVP, the Mets began making offers, even trying to get the Rays to chime in with a three-team deal. It would have involved giving Boston Mike Cameron and Lastings Milledge, but the stumbling block was picking up the remainder of Ramirez’s $64 million contract. In the end, the deal never came off so Manny stayed in Boston a few more years to the detriment of Mets fans.
15 Carlos Beltran for Kevin Youkilis
The AL Rookie of the Year, Carlos Beltran had been impressive with Kansas City but was headed for free agency at the end of 2004. Thus, the Royals wanted to move him out for someone else before he left. They reached out to the Red Sox and a deal was made for Kevin Youkilis with catcher Kelly Shoppach thrown in too.
It went to the wire but the Royals instead traded Beltran to the Astros. Beltran would bounce around various teams, building up his All-Star career before returning to Houston to help the Astros to a World Series victory. Yet that could have been a great addition to Boston in this time period.
14 Ted Lilly for Ryan Howard
Phillies fans should send thank-you notes to J.P. Ricciardi. In early 2005, the Blue Jays were given an offer from Philadelphia to send over rookie first baseman Ryan Howard in exchange for Ted Lilly.
Ricciardi refused, saying they had Lilly signed for another year and were confident he’d stay longer and be a cornerstone for a young team.
Howard was soon the regular first baseman for the Phillies and “the Big Piece” is now one of the most loved Phillies ever. After the failed deal, he became the NL Rookie of the Year, the 2006 MVP, twice led MLB in home runs and led the Phillies to the 2008 World championship. Retiring in 2016, it’s likely he’ll be in the Hall of Fame. And Lilly? After that one year, he was gone from Toronto.
13 Tim Raines for Tom Glavine
A seven-time All-Star, Tim Raines is best known for his long career in Montreal as a huge star. “Rock” also ended up achieving big success outside Montreal, winning two World Series with the Yankees. But in 1990, Montreal was worried Raines was on the downside of his career and worked out a trade with Atlanta. Raines would have gone to the Braves in exchange for a young pitcher named Tom Glavine.
It fell through at the last minute with Raines instead heading to the Chicago White Sox. Atlanta fans should be happy as Glavine became a key reason the Braves dominated in the early 1990s, winning the ’95 World Series. Meanwhile, Raines ended up with a couple of rings of his own to show how things worked out well.
12 Justin Verlander And Curtis Granderson To The Marlins
In 2005, Dontrelle Willis had a great year in Florida, going 22-10 with a 2.63 ERA. Thus, the Tigers became convinced he could be the solution to their pitching woes and made a huge offer of Justin Verlander and Curtis Granderson. In the end, the Marlins decided to keep Willis, thinking he’d be their star.
Instead, Willis never came close to that great 2005 season and the Marlins were trying in vain to unload him the next year.
Granderson was able to continue on to his career as a three-time All-Star while Verlander has led the AL in strikeouts four times, been the MVP and Cy Young winner and won a World Series with the Astros.
11 David Wright to the Blue Jays
Yep, it’s Toronto again. It’s as if GM J.P. Ricciardi specialized in huge deals that could have brought major success to the team only to call them off for the dumbest reasons. One of his worst was in 2002 as the Mets offered to hand over David Wright in exchange for Jose Cruz, Jr. Ricciardi kept Cruz, despite his poor batting, famously bad-mouthing Wright’s potential as someone from “the Sally League.” Cruz was gone after 2003 while Wright went on to become a 7-time All-Star and current Mets captain. No wonder Toronto fans hate J.P. so much.
10 Miguel Cabrera to the Angels
Here’s another one for the Marlins. Miguel Cabrera had been part of the Marlins’ 2003 World championship team and still a good player but was headed for free agency as 2007 closed out. Thus, the Marlins approached the Angels with the idea of trading Carbrera off as part of a huge multi-player trade that could have brought any number of Angels to Florida. But the Marlins insisted that Carbrera’s $7 million salary be part of the deal which caused the Angels to balk. The Tigers took a chance to open up their wallet to get Carbrera and Dontrelle Willis for several players. It was worth it as Carbrera became a two time AL MVP and won the Triple Crown while keeping the Tigers in contention.
9 Alex Rodriguez to the Red Sox
In 2003, the Red Sox were hurting after a heartbreaking loss in the ALCS. They needed to shift things up and thus worked on a huge trade with the Rangers. The idea was to send Manny Ramirez and Jon Lester in exchange for Alex Rodriguez. A side deal would include the White Sox but Rodriguez was the key to it all.
Rodriguez actually agreed to lose almost $30 million in the deal but the Players Association disagreed and vetoed the deal.
As everyone knows, the Yankees ended up trading to get A-Rod. Of course, the Red Sox ended up winning the World Series the next year so it ended up working out well but still notable how close A-Rod came to going to Beantown.
8 Mariano Rivera to the Mariners
During his tenure with the Yankees, Mariano Rivera could have been traded almost five different times. The biggest was in 1996, Rivera’s second year in the majors and not exactly showing off any real skill. With several injuries abounding, George Steinbrenner worked out a deal to send Rivera to Seattle for veteran shortstop Felix Fermin.
Thankfully, others in management were able to talk Steinbrenner out of that. Fermin would be gone after that season while Rivera would turn into one of the best closers in baseball with five World Championships and the MVP of the ’99 Series. Good thing George was able to temper himself this time around.
7 Pedro Martinez to Cleveland for Jaret Wright and Bartolo Colon
Maybe the Indians could have gotten a World Series if this deal had gone through. In 1997, they were smarting after losing the Series to the Marlins and wanting to spark things up.
So they agreed to a deal with the Expos to trade pitcher Jaret Wright and Bartolo Colon for NL Cy Young winner Pedro Martinez.
It fell apart at the last minute and thus Cleveland slumped in the 2000s. Meanwhile, the Red Sox managed to get Martinez years later to be a key part of their 2004 World Series team just to remind Indians fans what they could have had.
6 Randy Johnson to the Blue Jays
It’s well known how several teams missed the boat on Randy Johnson. The Expos traded him off before he took off, Seattle gave him to Houston and the Astros let him go after just one season. That paved the way for Johnson’s brilliant work helping Arizona win the World Series, becoming MVP of that game and one of the best pitchers of his time.
In 1993, the Blue Jays were trying to bounce back and began a multi-team trade with the hopes of getting Johnson from Seattle. However, Mariners GM Woody Woodward was golfing and couldn’t be contacted before the trade deadline was up. Thus, due to bad timing, Toronto missed the chance to get a Hall of Fame pitcher that they could have used well.
5 Albert Pujols to the Expos
There are some complaints over Albert Pujols being worth his high contract with the Angels. But in his prime, the man was a fantastic star for the Cardinals. A three-time MVP, he helped St. Louis to two World championships and is a ten-time All-Star. Yet, that almost didn’t happen. In December of 2000, the Cardinals traded third baseman Fernando Tatis and reliever Britt Reames to Montreal for relievers Dustin Hermanson and Steve Kline.
According to reports, the Expos came quite close to taking Pujols instead of Tatis but decided to go with a more experienced man.
Thus, Pujols was able to start with St. Louis and win Rookie of the Year honors to kick off his great career that could have begun in Montreal.
4 Alex Rios For Tim Lincecum
This was a trade buzzed about back in 2007 and might have changed a couple of teams. Alex Rios had been a good player for Toronto but they weren’t quite sure if he was worth keeping. So they started approaching the Giants to trade him for rookie Tim Lincecum. Ironically, at the time, Giants fans thought Rios was the guy to get and begging the trade to go down but it never did. Rios instead spent time with the Blue Jays, then the White Sox before winning a World Series with the Royals.
Meanwhile, Lincecum became a fantastic ace for San Francisco with 2 Cy Young Awards, a three-time strikeout leader, two no-hitters and three World Series championships. Looks like this deal falling through helped the Giants after all.
3 Barry Bonds to Atlanta
One of the dumbest moves by the Pirates was letting Barry Bonds go for nothing. The slugger was a key reason the Pirates had won three straight divisional titles but made noise about wanting a bigger contract that Pittsburgh wouldn’t pay.
Figuring if he wanted out, it was better to get something in return, the Pirates planned to send Bonds to Atlanta for Alejandro Pena, Keith Mitchell and a player to be named later.
However, manager Jim Leyland was outraged at the idea of Bonds being given away like that and called the whole thing off. Thus, Bonds was allowed to play out his contract and embark on his great career in San Francisco, leaving the Pirates with nothing to show for his absence.
2 George Brett To Cincinnati For Tony Perez
The idea of George Brett in anything but a Kansas City Royals uniform is hard to imagine. Brett was easily one of the most popular players in team history, a 13 time All Star, AL MVP and part of the Royals 1985 World Champions team. However, according to Brett, in 1974, his second year, the Royals were considering trading him to the Reds in exchange for Tony Perez. At the time, the Reds were “The Big Red Machine” dominating the NL and any player from them was worth grabbing. It fell through at the last minute as the Reds decided to hold off on breaking up the Machine. Kansas City fans are more than happy for that to gain a Hall of Famer who’s still Kansas City Royalty.
1 Ted Williams for Joe DiMaggio
Had this happened, the entire course of baseball history would have been changed. In 1947, the Yankees were coming off another World Series win while the Red Sox had just missed on the pennant. Meeting at a bar, Yankees owner Dan Topping and Red Sox owner Tom Yawkey got to talking and agreed in principle to send Joe DiMaggio to Boston for Ted Williams. The idea of the two biggest stars of the time swapping teams would have rocked the baseball world. It never happened as in the morning, each man slept on it enough to realize their respective fanbases would be outraged over this and called it off (although supposedly Yawkey asked for Yogi Berra too).
Needless to say, the effects would have been massive. With DiMaggio, it’s easy to imagine the Red Sox winning the World Series a couple of times and the “Curse” ending 55 years earlier. On the other hand, Williams could have kept the Yankees powered up with his slugging to remain a dynasty. Either way, it’s astounding how close this storied rivalry came to such a major shift.