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
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.
The deal fell apart due to medical concerns, with conflicting reports about whether it was due to Wheeler's injury or a hip problem with Gomez. The Brewers traded Gomez to the Astros instead and the Mets traded for Yoenis Cespedes, whose play down the stretch helped them to reach the postseason and make an appearance in the World Series.
13 Royals Trade Carlos Beltran To The Red Sox Or Yankees
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.
Either deal may have worked out well for the Royals, but instead they opted to move Beltran to Houston in a three team deal with Oakland that brought Athletics third baseman Mark Teahen and pitcher Mike Wood to Kansas City along with Astros catcher John Buck.
12 Mets Trade David Wright To The Blue Jays for Jose Cruz, Jr.
As you'll see throughout this list, J.P. Ricciardi's tenure as general manager of the Toronto Blue Jays was filled with missed opportunities. In 2002 he discussed a trade with Mets GM Steve Phillips in which he was offered single-A third baseman David Wright for outfielder Jose Cruz, Jr. Ricciardi decided to hold on to Cruz, Jr., who was batting around .230 with a .300 OBP at the time, and reportedly toldPhillips, “I’m not trading a major league player for some guy in the Sally League.” Cruz, Jr. would leave the Blue Jays as a free agent at season's end to sign with the Giants, while Wright has gone on to become a seven time All-Star in New York.
11 Phillies Trade Ryan Howard To The Blue Jays for Ted Lilly
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."
After the season the Phillies traded Thome to the White Sox, opening up first base for Howard. The following year, Howard would take home NL MVP honors after leaving the yard 58 times in his first of four consecutive seasons with at least 45 home runs. Lilly, meanwhile, would play one more season as a Blue Jay before leaving as a free agent.
10 Royals Trade Zack Greinke To The Nationals
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."
Greinke was instead dealt to the Brewers in a package that included Lorenzo Cain and Alcides Escobar, playing a key role in their path to becoming the 2015 World Series Champions.
9 Blue Jays Trade Alex Rios To The Giants for Tim Lincecum
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.
Two years later Lincecum would have two NL Cy Young Awards to his name, while Rios was allowed to be claimed off waivers by the White Sox for nothing after failing to live up the expectations of a seven-year, $69-million extension.
8 Tigers Trade Justin Verlander and Curtis Granderson To The Marlins For Dontrelle Willis
Dontrelle Willis had a career year for the Florida Marlins in 2005, going 22-10 with a 2.63 ERA and finishing second to Chris Carpenter for the NL Cy Young Award. The Marlins reportedly received a trade offer from the Detroit Tigers that included a pair of youngsters in Justin Verlander and Curtis Granderson, but opted to hold onto Willis believing that he was only going to get better. Within two years, the Marlins were trying to rid themselves of Willis and the Tigers were able to acquire him without giving up a future three-time All-Star in Granderson and a future Cy Young and MVP Award winner in Verlander.
7 Cardinals Trade Albert Pujols To The Expos
In 2000 the St. Louis Cardinals were looking for some pitching depth and worked out a trade with the Montreal Expos for relievers Dustin Hermanson and Steve Kline. The Cardinals agreed to part with reliever Britt Reames, but had to decide whether to give up third baseman Fernando Tatis or first base prospect Albert Pujols. They chose to part with Tatis in part because, according to Cardinals manager Tony LaRussa, he had shown a "lack of desire and personal discipline" after signing a contract extension. Pujols would make his Major League debut the following season, taking home the NL Rookie of the Year Award in his first of 12 consecutive 30 plus home run seasons for the Cardinals.
6 Marlins Trade Miguel Cabrera To The Angels
In 2007, the Florida Marlins wanted to trade slugger Miguel Cabrera before he could reach free agency. They discussed a deal to send him to the Angels with Ervin Santana, Joe Saunders, Nick Adenhart, Brandon Wood, Howie Kendrick, Kendrys Morales, Reggie Willits and Jeff Mathis among the names that may have been discussed to come back the other way. However, after refusing to part with Dontrelle Willis a couple of years earlier, the Marlins were now insistent that he and his $7 million salary be included in any trade for Cabrera. The Tigers were still willing to take a chance on Willis and send back minimal salary in return, so the Marlins opted for their package of prospects instead.
6. Blue Jays Trade For Randy Johnson
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.
The deal wasn't done there, though. Henderson wanted to be paid to accept the move and why the negotiations were going on, Woodward called Gillick to tell him that he would make the Johnson trade. Having already given his word to A's General Manager Sandy Alderson, Gillick backed out of the deal with Seattle and finalized the trade for Henderson. As a rental, Henderson helped the Blue Jays to another World Series title, but Johnson would've provided them with a top tier starter through the bleak years that followed.
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.
That World Series would prove to be the peak of Wright's career and although the Indians robbed the Expos four and half years later when they traded Colon for a package that included Cliff Lee, Grady Sizemore, and Brandon Phillips, a trade for Martinez might have been what the Indians needed to get them over the hump after their second World Series loss in three years.
4 Yankees Trade Mariano Rivera To The Mariners
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.
Steinbrenner worked out a trade with the Mariners that would've sent either Rivera or Bob Wickman to Seattle for veteran shortstop Felix Fermin, but Yankees management ultimately convinced their owner to hold off on the deal. Fermin had just 16 more at bats in his career while Jeter went on to win Rookie of the Year and become the face of the franchise and Rivera became the most dominant closer the game has ever known.
3 Pirates Trade Barry Bonds To The Braves
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.
However, when Pirates manager Jim Leyland found out about the trade, he was livid and stormed into the team president's office to give him a piece of his mind. The trade was called off and Bonds played out the final year of his deal in Pittsburgh before leaving for San Francisco.
2 Rangers Trade Alex Rodriguez To The Red Sox
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.
That same offseason, Aaron Boone suffered a knee injury in a pick-up basketball game that would cause him to sit out all of 2004 and the Yankees traded for Rodriguez as a replacement. The non-trade worked out well for Boston. The following autumn they would complete an improbable comeback from a 3-0 series deficit against those same Yankees en route to their first World Series victory in 86 years with Ramirez taking home World Series MVP honors.
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.