Top 15 Huge MLB Trades That Almost Happened

There's an old adage in sports that "sometimes the best trades are the ones you don't make", meaning it can often work out better for your team if you hold off on making a deal that could hurt your team in the long run. Often times this holds true; a player you may traded away ends up helping you win a championship or develops into a star or a player that you considered trading for shows a drop-of in play. However, the reverse can also be true and you may end up regretting holding of on a deal for the opposite reasons.

Building a baseball team is an inexact science. Deciding which trades are the right ones to make and which moves to hold off on isn't always easy. General managers get paid big bucks to make the right calls and some do it much better than others, but everyone has deals that hit and deals that miss and sometimes a trade breaks down for reasons that are out of your control.

Out of all the trades that are discussed, the vast majority of them never see the light of day. We are often robbed of blockbuster deals without ever knowing about it. Fortunately, there are times when deals come so close that they are reported by the media or talked about by one side years later. With the development of social media, the leaking of potential trades has only become more prevalent. It's fun to look back at what might have been, although if you're a fan of a team that passed on major, franchise altering deals like the Blue Jays and Indians did, you may want to rip your hair out after reading this list.

Nevertheless, here are the top 15 huge MLB trades that almost happened:

14 Mets Trade For Carlos Gomez

Thomas B. Shea-USA TODAY Sports

This past summer, the New York Mets work looking for an upgrade in the outfield and agreed to trade young shortstop Wilmer Flores and injured starting pitcher Zack Wheeler to the Milwaukee Brewers for Carlos Gomez. When word of the potential deal spread to the players, Flores, who was on the field playing for the Mets, could be seen crying. After the game, Mets GM Sandy Alderson said that no deal had been completed and blamed people on social media for getting ahead of themselves.

13 Royals Trade Carlos Beltran To The Red Sox Or Yankees

Andy Marlin-USA TODAY Sports

With star outfielder Carlos Beltran headed towards free agency at the end of the 2004 season, the Kansas City Royals were looking to move him, but insisted that any trade would require a third baseman and a catcher as the return. The Red Sox offered third baseman Kevin Youkilis and catcher Kelly Shoppach. The Yankees offered Robinson Cano, who was still playing in the minors and was moved from second base to third to showcase for a trade, and catcher Dioner Navarro.

12 Mets Trade David Wright To The Blue Jays for Jose Cruz, Jr.

Steve Mitchell-USA TODAY Sports

11 Phillies Trade Ryan Howard To The Blue Jays for Ted Lilly

Eric Hartline-USA TODAY Sports

In 2005, Jim Thome was still the Philadelphia Phillies starting first baseman, so the team was willing to part ways with a young Ryan Howard. They reportedly offered Howard to the Blue Jays for mid-rotation starter Ted Lilly, but Ricciardi turned the offer down. "I'm not trading Lilly," he said. "He's signed through next year to a reasonable contract, he's a starting pitcher and we're trying to build a winning atmosphere for the kids like Aaron Hill and Russ Adams, who are winning players who need to be playing in a winning atmosphere."

10 Royals Trade Zack Greinke To The Nationals

Rick Scuteri-USA TODAY Sports

Prior to the 2011 season, the Kansas City Royals were looking to trade starting pitcher Zack Greinke in order to maximize their return before he could reach free agency at the end of the 2012 season. They discussed a deal to ship him to the Nationals with Drew Storen, Danny Espinosa, and Jordan Zimmermann among the names that may have been in the possible return, but the Nationals were on Greinke's no-trade list and he turned the deal down. They had yet to win a division title and Greinke was not confident that they could turn things around. In a 2013 interview he said, “I was in a different league [back then] and never saw them play, so I didn’t really have a good feel for what they had. They were telling me how good their young guys were and I didn’t really want to take 100 percent of their word for it and just complete trust what people are saying. But, I mean, they were right about what they were saying."

9 Blue Jays Trade Alex Rios To The Giants for Tim Lincecum

via Benny Sieu-USA TODAY Sports

Rounding out our trio of Ricciardi's non-deals, is a trade that he discussed with Giants GM Brian Sabean at the 2007 Winter Meetings. The deal would've seen young starter Tim Lincecum head to Toronto for outfielder Alex Rios. The Giants were in need of some offense and Rios was viewed to bea rising star. There's been speculation that the Giants may have been willing to part with starter Matt Cain to get a trade done, but Riccardi was insistent on getting Lincecum in return. After the Giants signed free agent Aaron Rowand to a five-year, $60-million deal, they no longer pursued Rios.

8 Tigers Trade Justin Verlander and Curtis Granderson To The Marlins For Dontrelle Willis

via Rick Osentoski-USA TODAY Sports

7 Cardinals Trade Albert Pujols To The Expos

Jim Cowsert-USA TODAY Sports

6 Marlins Trade Miguel Cabrera To The Angels


At the 1993 trade deadline, Blue Jays GM Pat Gillick was looking to beef up his roster in anticipation of a run to a second consecutive World Series title and had two major deals on the table. One would send pitchers Steve Karsay and Mike Timlin to the Mariners for starter Randy Johnson, while the other would ship Karsay and a player to be named later to the Athletics for Rickey Henderson. Gillick preferred to pull the trigger on the Johnson deal, but couldn't get a hold of Mariners General Manager Woody Woodward, who was golfing at the time, so he accepted the Henderson trade.

5 Indians Trade For Pedro Martinez


Jaret Wright began the 1997 season pitching in double-A. The 21-year-old, former 10th overall pick ended the year starting in game seven of the World Series for the Cleveland Indians. After the Indians lost, they had the opportunity to trade Wright, young starter Bartolo Colon, and others to the Montreal Expos for reigning NL Cy Young Award winner Pedro Martinez. Indians GM John Hart decided against it and Martinez was instead traded to the Red Sox in a deal for Carl Pavano.

4 Yankees Trade Mariano Rivera To The Mariners

Brad Penner-USA TODAY Sports

Believe it or not, the Sandman was nearly traded out of New York no fewer than five times, including two separate deals for David Wells. The most impactful non-deal, however,came in the spring of 1996. Rivera had yet to establish himself as a dominant closer and had posted an ERA of just 5.51 in his rookie season in 1995. With injuries to infielders Tony Fernandez and Pat Kellyand rookie shortstop Derek Jeter having struggled through spring training, George Steinbrenner was unsure if he could rely on Jeter.

3 Pirates Trade Barry Bonds To The Braves

Steve Mitchell-USA TODAY Sports

In 1992 Barry Bonds was heading into the final year of his contract with the Pittsburgh Pirates and likely bound for free agency. Not wanting to lose the future home run king for nothing, the Pirates agreed to trade Bonds to the Atlanta Braves, who were looking to bulk up their talented roster and were confident they could sign Bonds to an extension. Pitcher Alejandro Peña, outfielder Keith Mitchell, and a prospect to be named later were going to Pittsburgh in the deal.

2 Rangers Trade Alex Rodriguez To The Red Sox

Greg M. Cooper-USA TODAY Sports

After Aaron Boone hit a walk-off home run to lead the New York Yankees past the Boston Red Sox in the 2003 playoffs, the Red Sox set out to make a big offseason move. They orchestrated a blockbuster trade to acquire star shortstop Alex Rodriguez from the Texas Rangers for star outfielder Manny Ramirez and pitching prospect Jon Lester. They also planned to ship incumbent shortstop Nomar Garciaparra to the Chicago White Sox for outfielder Magglio Ordonez and pitching prospect Brandon McCarthy in a subsequent deal. However, the Rodriguez trade would've required him to sacrifice $28-30 million in salary and although he agreed to it, the MLB Players Association had no interest in allowing it to happen, killing both trades.

1 Red Sox Trade Ted Williams To The Yankees For Joe DiMaggio


It would've been, arguably, the biggest trade in the history of baseball between the game's two biggest rivals. As the story goes, in 1947 Yankees owner Dan Topping and Red Sox owner Tom Yawkey had a little bit too much to drink one night and agreed to a trade that would've seenone of the game's all-time greatest hitters, Ted Williams, go to New York with the Yankee Clipper, Joe DiMaggio, headed back to Boston. The pair figured that their each of their stars would be better suited playing in the other's ballpark. When Yawkey awoke the next morning, he decided to reject the trade but allegedly asked Topping to include rookie outfielder Yogi Berra to make the deal happen.

The trade never came to fruition and baseball fans were deprived of a blockbuster. The deal would've had a massive effect on the game, but likely would've worked out better for the Yankees than the Red Sox. DiMaggio played just 625 more games after the failed trade while Williams went on to play another 1,556.

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Top 15 Huge MLB Trades That Almost Happened