As we inch toward the start of summer, trade chatter around Major League Baseball will inevitably heat up in anticipation of the July 30 Trade Deadline. But some teams in years past haven’t waited until the last minute to do their midseason shopping. Many have pulled off deals that involved MVPs, Cy Young Award winners, postseason legends and future Hall of Famers. This month has seen trades that either catapulted teams and players to immediate success or set the foundation for future greatness.
Here is a rundown of the most impactful trades in the month of June since the Trade Deadline was moved to July in 1986.
Trades that paid off immediately
June 28, 2018: An unlikely World Series hero
The 2018 Red Sox were loaded with star power, but 35-year-old journeyman Steve Pearce was their best player on the biggest stage. Sent from the Blue Jays for light-hitting infielder Santiago Espinal, Pearce clobbered three home runs in the final two games of the 2018 World Series as the Red Sox beat the Dodgers in five games. Pearce was named the World Series MVP and joined Babe Ruth and Ted Kluszewski as the only players 35 or older to hit two homers in a World Series game.
June 24, 2004: Beltrán blasts off in October
The Royals sent Carlos Beltrán to Houston in the middle of 2004 and in the prime of his career. The trade involved three teams and five players, but what most remember about the deal is the torrid run Beltrán went on during that year’s postseason. In 12 games between the NLDS and NLCS, he went 20-for-46 at the plate with eight homers, 14 RBIs, 21 runs scored and more walks than strikeouts. His brilliance brought the Astros to within one game of their first pennant. The players Kansas City received in the trade — Mark Teahen, Mike Wood and John Buck — would not make Royals fans forget about their homegrown star.
June 29, 2000: Justice helps Yanks three-peat
A 34-year-old David Justice had one of the best seasons of his career in 2000. He did most of his damage for the Yanks, who acquired him from Cleveland for three prospects, including Ricky Ledee and Jake Westbrook. Justice put together a .305/.391/.585 slash line in 78 regular-season games. He then hit a home run in two series-clinching games during the playoffs, including a go-ahead three-run shot in Game 6 of the ALCS, of which Justice was named the MVP. His efforts led the Yanks to their third consecutive World Series title. Although Ledee was viewed as the centerpiece of Cleveland’s return, it was Westbrook who provided the most value. He became a serviceable starter for Cleveland and made the AL All-Star team in 2004.
June 20, 1998: Leyritz adds to his postseason legacy
Jim Leyritz already had a reputation as a clutch postseason performer when the Padres obtained him from the Red Sox for three players. Leyritz cemented that reputation during the 1998 playoffs as he clubbed a home run in three consecutive NLDS games vs. the Astros. He added another homer in the NLCS against the Braves as San Diego advanced to its first World Series since 1984. Leyritz’s four homers are the second most by any Padre in a single postseason.
June 11, 1993: Fernandez becomes king out of Queens
Tony Fernandez began his career in Toronto, hitting .294 and making three All-Star teams in his first eight seasons. The Mets hoped he could provide that level of production when they struck a deal with San Diego to bring Fernandez aboard in October 1992. However, limited by an injury, Fernandez hit just .225 in 48 games before the Mets sent him back to Toronto for outfielder Darrin Jackson. While Jackson batted .195 in 31 games with the Mets, Fernandez rediscovered his old form with his old team. He slashed .306/.361/.442 during the regular season and drove in nine runs during the 1993 World Series as the Blue Jays repeated as champions. Those nine RBIs are tied for the most by a shortstop in any World Series.
June 21, 1989: Rickey goes back to the Bay
Both the A’s and Rickey Henderson weren’t happy in the middle of the 1989 season. The team was still stewing from its World Series loss in ’88; the player was off to a slow start for the floundering Yankees and wanted a new contract. Instead, the Yankees sent Henderson back to the team from which they acquired him five years earlier in exchange for Eric Plunk, Luis Polonia and Greg Cadaret. Henderson stole 52 bases in just 85 games with the A’s that summer, and he was exactly what Oakland needed to get over the hump as it swept the Giants in the World Series. He won the AL MVP Award the following season thanks in part to his 1.016 OPS.
Trades that paid off later
June 19, 2016: Taylor breaks out with Dodgers
The Dodgers’ acquisition of Chris Taylor for pitcher Zach Lee probably flew under many people’s radar. Taylor was a rarely used utility player on the Mariners who had matching career on-base and slugging rates of .296. Lee was a once-highly touted prospect whose star had dimmed a bit. But fast forward about 16 months, and Taylor was crowned the 2017 NLCS co-MVP, then hit a home run to open the scoring in Game 1 of the World Series. Later that month, Mariners general manager Jerry Dipoto said that this trade “is clearly the worst deal I’ve ever made.” Taylor was recently listed as the Dodgers’ most indispensable player in 2021. Lee had a 7.39 ERA in 14 starts at Triple-A Tacoma before Seattle cut its losses.
June 4, 2016: Padres find a phenom
The Padres made a bunch high-profile moves in 2015, adding the likes of Craig Kimbrel, Matt Kemp and James Shields to their roster. But by 2016, it was clear that the plan wasn’t working and a reset was needed. San Diego found a buyer for Shields in the White Sox, who saw the veteran righty as a stabilizing force for their rotation. For his services, Chicago dealt pitcher Erik Johnson and a toolsy 17-year-old shortstop who had yet to play in pro ball by the name of Fernando Tatis Jr. Shields posted a 5.31 ERA and a 1.9 HR/9 rate with Chicago from 2016-18. Johnson was a former Top 100 Prospect, but never really caught on in the Majors. Tatis, on the other hand, has caught on quite well.
June 30, 2006: Indians unearth All-Star shortstop
First baseman Eduardo Perez began 2006 by hitting .303 with a .979 OPS in 108 at-bats for the Indians. That was enough for the Mariners to go out and get the 35-year-old, and they sent shortstop Asdrúbal Cabrera back to Cleveland. Perez’s production tanked in Seattle — he put up a .545 OPS — and by October of that year, he had retired and was already in an ESPN booth. The 20-year-old Cabrera would go on to have a couple of All-Star campaigns and play a significant role on two playoff teams during his eight seasons with the Indians.
June 8, 2005: Polanco becomes big hit with Tigers
The Phillies’ addition of Ugueth Urbina to bolster their bullpen was the original headline of this deal. But that didn’t pan out as Urbina posted a 4.13 ERA for Philadelphia, which fell shy of the playoffs in 2005. The real story was whom the Phillies sent to Detroit. Placido Polanco became an All-Star, a two-time Gold Glove winner and a Silver Slugger recipient with the Tigers. He was integral in their drive to the AL pennant in 2006. He went 16-for-34 at the plate in his first eight postseason games that year, and he was named ALCS MVP thanks to a .529/.579/.588 slash line.
June 27, 2004: Garcia ends White Sox title drought
After pitcher Freddy Garcia logged nearly 1,100 innings in fewer than six full seasons in Seattle, the Mariners traded their innings-eater to the White Sox for Mike Morse, Miguel Olivo and Jeremy Reed. Garcia was at his best in 2005 as he threw 228 innings in the regular season, a complete-game win over the Angels in the ALCS and seven shutout frames in the Game 4 clincher of the World Series vs. the Astros. Two innings after Garcia exited that game, he and the Sox celebrated the team’s first championship in 88 years.
June 27, 2002: Cleveland gets huge haul for Bartolo
The Expos made a big splash in 2002 in an effort to reach the playoffs, obtaining pitcher Bartolo Colon from the Indians. A premier workhorse, Colon already had a couple of 200-strikeout seasons on his ledger at age 29, so Cleveland presented a high asking price. And the Expos met it: Colon for Cliff Lee, Grady Sizemore, Brandon Phillips and Lee Stevens. Colon was solid in Montreal, but he wasn’t nearly enough to get the Expos into the postseason. Even though Stevens was a throw-in and Phillips didn’t blossom until he got to Cincinnati, the Indians were still left with a couple of franchise cornerstones. Lee won a Cy Young Award in 2008. Sizemore accumulated 27.3 fWAR from 2005-08 before dealing with a bevy of injuries and becoming one of the game’s most star-crossed players.
June 24, 1993: Padres land a franchise icon
The Marlins selected pitcher Trevor Hoffman with the eighth pick in the 1992 Expansion Draft. Seven months later, Florida traded him and two other prospects to San Diego for Gary Sheffield, who was already a bona fide star at age 24. This is the best example on this list of a trade that worked perfectly for both sides: Sheffield recorded a .970 OPS through parts of six seasons with Florida, including one that ended with a World Series victory. Meanwhile, Hoffman became a Padres legend, locked down 601 saves during his career and was only the sixth closer inducted into the Hall of Fame.
June 1989: Phillies build a pennant-winner
The Phillies, moribund in 1989, made four trades in June to change the course of the franchise. Three of those deals brought back players who helped turn the Phillies into NL champions just four years later. Future three-time All-Star John Kruk was acquired from the Padres (June 2), starting pitcher Terry Mulholland was part of a package from the Braves in return for Steve Bedrosian and Lenny Dykstra was added from the Mets. Mulholland and Dykstra both arrived on June 18. Mullholland was an All-Star in ’93, while Dykstra was the NL MVP runner-up that year as the Phillies won the pennant.
June 16, 1986: El Presidente to Les Expos
Dennis Martinez was a solid starter for the Orioles for a handful of years, but his career appeared to be winding down in 1986. Amid his fourth consecutive subpar season in Baltimore, the Orioles traded the 32-year-old Martinez to the Expos. He seemed to find the fountain of youth in Canada. From 1987-93, Martinez compiled a 2.96 ERA and a 126 ERA+ through more than 1,500 innings with Montreal. The 1991 season was his pièce de résistance as he posted an MLB-best 2.39 ERA, finished fifth in Cy Young voting and pitched the only perfect game in franchise history.