Most stunning offseason trades in history

December 16th, 2023

Every Hot Stove season comes with the potential of blockbuster deals, whether by free agency or trade. But there have been some offseason trades throughout baseball history that have particularly stunned us, catching us by surprise and creating exciting storylines for the upcoming season.

Here's a look at 16 of the most stunning offseason trades in MLB history.

Dec. 6, 2023: Padres trade Juan Soto and Trent Grisham to the Yankees for Michael King, Drew Thorpe, Jhony Brito, Randy Vásquez, and Kyle Higashioka

The Yankees entered the offseason needing to make a huge splash after going 82-80 -- their worst winning percentage since 1992 -- and missing the playoffs in 2023. As a result, the Yankees are acquiring superstar outfielder Juan Soto and Trent Grisham from the Padres, MLB Network insider Joel Sherman reported Wednesday night. The clubs have not confirmed the deal.

The Padres gave up an even larger haul to acquire Soto and first baseman Josh Bell from the Nationals at the 2022 Trade Deadline, sending CJ Abrams, MacKenzie Gore, Luke Voit, James Wood, Robert Hassell and Jarlin Susana to Washington. Sixteen months later, San Diego flipped Soto to New York in a Winter Meetings blockbuster that solved two problems for the Friars, giving them some much-needed payroll relief and bolstering their pitching staff.

Feb. 1, 2021: Rockies trade Nolan Arenado to Cardinals for Austin Gomber, Elehuris Montero, Tony Locey, Mateo Gil and Jake Sommers

After signing an eight-year extension with the Rockies during Spring Training in 2019, Arenado's tenure with the team came to an end with an offseason trade to the Cardinals.

Arenado had a down year in the shortened 2020 season, posting a .253 batting average with a .738 OPS and missing time in September with a shoulder injury. However, from 2015-19, the third baseman hit .300 with a .937 OPS while averaging 40 homers and 124 RBIs per season. Arenado also won a Gold Glove Award in each of his eight seasons with the Rockies, the second longest streak of such honors to start a player's career.

Jan. 7, 2021: Cleveland trades Francisco Lindor and Carlos Carrasco to Mets for Amed Rosario, Andrés Giménez, Josh Wolf and Isaiah Greene

After more than a year of rumors swirling around Lindor, a trade finally came to fruition when Cleveland not only sent its superstar shortstop to the Mets, but also included Carrasco in the deal.

Lindor, a four-time All-Star and two-time Gold Glove Award winner, had one year remaining on his contract and had just turned 27 years old at the time. He received a share of votes for the American League Most Valuable Player Award each season from 2016-19 before having a bit of a down year in the abbreviated '20 season. The Mets ensured Lindor would be staying in Queens for a long time to come when they inked the shortstop to a 10-year, $341 million extension on the eve of Opening Day.

Dec. 28, 2020: Cubs trade Yu Darvish and Victor Caratini to Padres for Owen Caissie, Ismael Mena, Reginald Preciado, Yeison Santana and Zach Davies

One day after acquiring former Cy Young Award winner Blake Snell from the Rays, the Padres continued the overhaul of their starting rotation by trading for Darvish from the Cubs. Darvish was coming off a tremendous performance during the pandemic-shortened 2020 campaign, posting a 2.01 ERA and 0.96 WHIP over 12 starts for Chicago.

Darvish's performance with San Diego has been inconsistent, with a strong 2022 campaign sandwiched between a pair of mediocre seasons in '21 and '23. Overall, he has a 3.87 ERA in three seasons with the Padres, and his strikeout rate has declined from over 30 percent to 27 percent since the trade.

On the other side of the deal, the only Major League piece the Cubs received, Davies, struggled to a 5.78 ERA in one season on the North Side before he signed as a free agent with the D-backs.

Results from the prospects that Chicago received have been a mixed bag so far -- Caissie is ranked as the organization's No. 3 prospect per MLB Pipeline, and he's coming off a strong 2023 campaign with Double-A Tennessee, hitting .289/.399/.519 with 22 homers in 120 games. The other outfielder the Cubs received in the Darvish deal is Mena, who has struggled to a .617 OPS in three Minor League seasons thus far.

The Cubs also received a pair of infielders -- Preciado, initially ranked as the club's No. 11 prospect upon arriving in the trade, and Santana (initially ranked No. 20). Preciado hasn't hit much in the Minors thus far and Santana was released in June 2023 following three injury-plagued seasons in the Minors.

Dec. 27, 2020: Rays trade Blake Snell to Padres for Luis Patiño, Cole Wilcox, Blake Hunt and Francisco Mejía

San Diego pulled off an astounding pair of blockbuster trades within a wild 24 hours, landing two of the best pitchers in baseball: Darvish and Blake Snell. The Padres managed to pry Darvish, who finished second in the NL Cy Young race in 2020, away from the NL Central champion Cubs for a quartet of young prospects (plus one established starter in Davies).

It was also stunning to see the Rays deal Snell, who had just led them to the 2020 World Series. A 28-year-old at the top of the sport, a Cy Young Award under his belt, getting traded fresh off a pennant run? You don't see that every day.

Feb. 10, 2020: Red Sox trade Mookie Betts, David Price and cash to Dodgers for Alex Verdugo, Jeter Downs and Connor Wong; Twins trade Brusdar Graterol, Minor League prospect and 67th pick in 2020 Draft to Dodgers for Kenta Maeda, Minor League prospect and cash

In an epic pair of deals involving three teams, a former American League MVP, a former AL Cy Young Award winner and multiple highly-touted prospects changed hands just days before pitchers and catchers were set to report to Spring Training. And these deals almost didn't happen at all.

Initially, a three-team trade involving the Dodgers, Red Sox and Twins was thought to be in place, wherein superstar right fielder Mookie Betts, former AL Cy Young Award winner David Price and cash would go from Boston to Los Angeles in exchange for outfielder Alex Verdugo and right-hander Brusdar Graterol, whom Los Angeles would acquire from Minnesota for right-hander Kenta Maeda.

But the deal hit a snag when Boston saw Graterol's medical review and determined he'd be better suited as a reliever rather than a starter, which was what the Red Sox were hoping for. So with Boston asking for more in return since starters are valued more highly on the market than relievers, it was several days before a reworked arrangement came to fruition, one that was actually two separate trades involving the three clubs.

In the end, the Dodgers, who were stunned with an early exit in the previous October's NL Division Series against the Nationals, made the blockbuster move with the Red Sox to acquire Betts and Price along with cash to offset about half of the remaining $96 million on Price's contract. Los Angeles sent Verdugo to Boston, but in place of Graterol included a pair of top prospects, middle infielder Jeter Downs (No. 44 prospect in baseball per MLB Pipeline) and catcher Connor Wong.

The Dodgers made a separate deal with the Twins to send Maeda, a Minor League prospect and cash to Minnesota in exchange for Graterol, the 67th overall pick in the 2020 MLB Draft and a Minor League prospect.

Dec. 3, 2018: Mets trade Jay Bruce, Anthony Swarzak, Gerson Bautista, Justin Dunn and Jarred Kelenic to Mariners for Robinson Canó and Edwin Diaz

The Mariners decided to rebuild after an 89-win season, as general manager Jerry Dipoto determined his roster was not strong enough to compete with American League powerhouses including the Red Sox, Yankees and Astros. Meanwhile, new Mets general manager Brodie Van Wagenen sought impact additions as he inherited a club coming off a disappointing 77-win campaign.

At the center of it all was Canó's massive contract, under which he was still owed $120 million over the remaining half of the 10-year deal he originally signed with Seattle prior to 2014. Canó was also coming off an 80-game suspension after he tested positive for a banned substance, further complicating his future in Seattle. Looking to clear up payroll space for his retooling efforts, Dipoto packaged Canó and Diaz -- the closer coming off a franchise-record 57-save season -- to New York in a deal that netted him both salary relief and a pair of top prospects in the right-hander Dunn and the outfielder Kelenic.

Dec. 9, 2015: D-backs trade Dansby Swanson, Ender Inciarte and Aaron Blair to Braves for Shelby Miller

Miller was an All-Star with the Braves in 2015, as the 24-year-old right-hander posted a 3.02 ERA in 33 starts and looked to have a bright future ahead of him. But the D-backs made an overwhelming offer, sending Swanson -- the first overall pick in the '15 Draft -- along with speedy center fielder Inciarte and right-hander Blair to Atlanta.

"We wanted to make it painful for [the D-backs] with players that we got back," Braves president of baseball operations John Hart said at the time. "They are players that we think are going to be a big part of our future."

Nov. 20, 2013: Tigers trade Prince Fielder to Rangers for Ian Kinsler

This deal was a stunner because Fielder, at age 29, had missed just one game in five years, and in two seasons with the Tigers had slashed .295/.387/.491 with 55 home runs. Nevertheless, Detroit dealt him to Texas in what proved to be a good move; Fielder would only have one more full season remaining in his career, with chronic neck injuries leading to his retirement at age 32.

Kinsler was an All-Star in his first season with Detroit, and was productive in his first three years as a Tiger, combining to hit .286/.332/.443 with 56 homers and 39 steals. He missed some time in '17 due to a hamstring injury, and hit .236/.313/.412 with 22 homers in 139 games. Kinsler was traded to the Angels after the '17 season and the Red Sox in July '18 before signing with the Padres. After a back injury ended his '19 season, Kinsler announced his retirement that December.

Nov. 19, 2012: Marlins trade Mark Buehrle, Jose Reyes, Josh Johnson, Emilio Bonifacio and John Buck to Blue Jays for eight players

The Marlins made a big splash on the free agent market following the 2011 season, as they prepared to open Marlins Park the next spring. Miami spent a combined $191 million to sign free agents Buehrle, Reyes and closer Heath Bell. It appeared the franchise was remaking itself, adding those established stars to a club that already featured slugger Giancarlo Stanton. But after a 69-93 season in '12, the Marlins traded Buehrle, Reyes and three other players to Toronto for eight players: Henderson Alvarez, Anthony DeSclafani, Yunel Escobar, Adeiny Hechavarria, Jake Marisnick, Jeff Mathis and Justin Nicolino.

Feb. 16, 2004: Rangers trade Alex Rodriguez to Yankees for Alfonso Soriano

This move was stunning not because Rodriguez was moved, but because he went to the Yankees. For weeks, it appeared that Rodriguez was destined for the Red Sox, and Boston was coming off a heartbreaking loss to New York in the American League Championship Series the prior October. Red Sox general manager Theo Epstein and company had a deal in place with Texas, and needed approval from the MLB Players Association to finalize a revised contract for Rodriguez, which would involve him reducing the total amount of his existing $252 million contract, of which $179 million remained.

The MLBPA declined to approve the contract restructuring proposal. Throughout this process, the Yankees -- another club Rodriguez had on his list of preferred trade destinations -- did not show interest in acquiring the superstar shortstop, because New York already had Derek Jeter at short, and ALCS walk-off hero Aaron Boone at third base.

But after the Rangers-Red Sox deal was nixed, Boone hurt his knee playing a pick-up basketball game, opening a window for A-Rod in the Bronx. While it appeared at the time that New York had once again gotten the better of Boston, the Red Sox defeated the Yankees in that October's ALCS with an epic comeback after being down three games to none, going on to win their first World Series title in 86 years.

Feb. 18, 1999: Blue Jays trade Roger Clemens to Yankees for David Wells, Homer Bush and Graeme Lloyd

Clemens was coming off his second consecutive AL Cy Young season with Toronto, and fifth overall. The right-hander remained his dominant self in his age-35 season, and invoked a clause in his contract in which he was permitted to demand a trade. The Blue Jays tried to strike a deal with the Yankees in mid-December, but New York was unwilling to part with top prospects, and an agreement seemed unlikely.

But in a stunning turn of events, and after Clemens had retracted his trade demand, the two sides reached an agreement that didn't cost New York any top prospects. Instead, the Yankees sent David Wells and a pair of lower-level prospects to Toronto, landing The Rocket in one of the most significant transactions in franchise history.

Dec. 5, 1990: Padres trade Roberto Alomar and Joe Carter to Blue Jays for Fred McGriff and Tony Fernandez

This trade was not only stunning, but also very consequential, particularly for Toronto. Alomar and Carter would be integral to the Blue Jays' back-to-back World Series titles in 1992 and '93, with Carter joining Bill Mazeroski (1960) as the only players to hit a walk-off home run to win the World Series when his shot over the left-field wall ended Game 6 against the Phillies in '93.

Alomar would be named an All-Star in all five seasons he spent with Toronto -- the future Hall of Famer hit .307/.382/.451 and also won five Gold Glove Awards at second base in that span. Carter hit 203 homers while being selected as an All-Star four times in seven seasons with the Blue Jays.

On the other side of the deal, neither McGriff nor Fernandez would be with the Padres for long. McGriff finished in the top 10 in NL MVP balloting in 1991 and '92, posting a .920 OPS with 66 homers over that span. Fernandez was productive for San Diego, too. The second baseman hit .274/.337/.359 and earned an All-Star selection from 1991-92. By the end of the '93 campaign, both had been traded, along with slugger Gary Sheffield.

The Padres traded McGriff to the Braves and Fernandez to the Mets. McGriff went on to hit 130 home runs and earn three All-Star selections over the next four-plus seasons, helping Atlanta win the 1995 World Series. In all, the slugging first baseman belted 493 career home runs and was inducted into the Hall of Fame in 2023. Fernandez played eight more seasons, eventually finding his way back to Toronto, where he was an All-Star in 1999.

Dec. 10, 1984: Expos trade Gary Carter to Mets for Hubie Brooks, Mike Fitzgerald, Herm Winningham and Floyd Youmans

Carter was an institution in Canada, and one of the most popular players in Expos history. In 11 seasons with Montreal, he was a seven-time All-Star, won three Gold Glove Awards, and had slashed .272/.345/.461 with 215 home runs. He also hit .429 with four doubles and a pair of homers in Montreal's run to the NL Championship Series in 1981.

The move was stunning, but the Expos were looking to improve at multiple positions after a fifth-place finish in the NL East in '84. Carter would go on to play five seasons for the Mets, being selected to the NL All-Star team four times and finishing third in NL MVP voting in '86, the year he helped New York beat the Red Sox to win the World Series.

April 5, 1972: Expos trade Rusty Staub to Mets for Tim Foli, Mike Jorgensen and Ken Singleton

Staub was known affectionately as "Le Grand Orange," and became immensely popular in Montreal after being traded to the Expos by the Astros in 1969. He performed well on the field -- hitting .296/.404/.501 with 78 homers in three seasons, in each of which he was an All-Star -- and endeared himself to the fans by learning to speak French.

"I felt I should be able to communicate with the people of Montreal in their own language," he told Sports Illustrated in '70. "After all, they were interested in baseball. I thought I should be interested enough in them to learn how to converse with them."

The trade was a shock to the baseball community in Montreal, and Staub went on to spend four seasons with the Mets and four with the Tigers before Detroit traded him back to Montreal in '79. His second stint with the franchise was brief, however -- he only played 38 games for the Expos before being traded the following March to the Rangers.

Dec. 9, 1965: Reds trade Frank Robinson to Orioles for Jack Baldschun, Milt Pappas and Dick Simpson

Robinson was a tremendous talent, and had proven it with Cincinnati by hitting .303/.389/.554 with 324 home runs over 10 seasons with the club. He was the 1956 NL Rookie of the Year, and the '61 NL MVP. Yet Reds general manager Bill DeWitt said the future Hall of Famer had reached his peak by that point, and sent him to Baltimore following the '65 season.

The centerpiece in the return for Robinson was Pappas, a two-time All-Star right-hander with a 3.24 ERA in nine seasons with the Orioles. He only spent two and a half seasons with Cincinnati, posting a 4.04 ERA in 82 appearances (75 starts) before being traded to the Braves in June of '68.

Meanwhile, Robinson went on to put up even better numbers in six seasons with Baltimore, slashing .300/.401/.543 with 179 homers, becoming the first player to win the MVP Award in each league by doing so in his first AL season with the Orioles in '66. That year, he also won the Triple Crown and led Baltimore to a World Series championship.