The most consequential trade deadline deals in MLB history



History is full of MLB trade deadline acquisitions who put a team over the top.

From David Justice to CC Sabathia to Yoenis Cespedes, there are decades-worth of examples of how a mid-summer deal can provide the missing piece for a playoff run or World Series championship.

There is similarly no shortage of in-season swings that backfired spectacularly.

With this year’s July 31 deadline days away, here is a look  at some of the most consequential pre-deadline trades of all time.

JOHN SMOLTZ, 1987

Perhaps the most notable deal to backfire was the Detroit Tigers’ acquisition of 36-year-old Doyle Alexander before the 1989 deadline.

To acquire the veteran, the Tigers sent John Smoltz, then a minor-league prospect, to the Atlanta Braves.

Alexander was excellent for Detroit, going 9-0 with a 1.53 ERA after the trade, but the Tigers did not make the World Series, and Smoltz went on to have a Hall of Fame career as the only pitcher with more than 200 wins and 150 saves.

RICKEY HENDERSON, 1989

Historically, the Yankees have been on the better ends of their mid-season deals, but sending the speedy Henderson to Oakland in June of 1989 was a costly exception.

Unable to reach an extension with Henderson — who was an impending free agent in the midst of a down year — the Yankees traded him to the A’s for Eric Plunk, Greg Cadaret, and Luis Polonia.

Henderson batted .294 and with 52 steals in 85 games after the trade, then hit .441 with 11 steals in the postseason. Henderson was that year’s ALCS MVP and led the A’s to what remains the franchise’s most recent title.

Famously, Plunk was also part of the 1984 trade in which the Yankees acquired Henderson from the A’s.

JEFF BAGWELL, 1990

In a worthy contender for worst deadline deal ever, the Boston Red Sox acquired reliever Larry Andersen from the Houston Astros for then-prospect Jeff Bagwell.

Andersen made only 15 appearances with Boston, then left in free agency.

Bagwell spent his entire 15-year Hall of Fame career with the Astros, hitting 449 home runs and winning National League MVP in 1994.

MARK MCGWIRE, 1997

The St. Louis Cardinals’ acquisition of the power-hitting sensation from the A’s that July didn’t propel them to the playoffs.

But it began a five-season partnership with McGwire that included him setting the short-lived single-season home run record with 70 in 1998.

All it cost the Cards was T.J. Mathews, Eric Ludwick and Blake Stein.

DAVID JUSTICE, 2000

Seeking their fourth championship in five years, the Yankees knew they needed another bat.

Justice was served.

The Yankees acquired the then-34-year-old Justice for Zach Day, Ricky Ledee and Jake Westbrook. They received immediate results, as Justice hit .305 with 20 homers and 60 RBI in 58 games after the trade.

Justice was even more crucial in the playoffs, hitting a go-ahead three-run home run in Game 6 of the ALCS en route to MVP honors for that round. The Yankees then beat the Mets in the World Series to complete a three-peat.

BOSTON RED SOX, 2004

The Red Sox made multiple moves in the summer of 2004 that helped them break the Curse of the Bambino.

The biggest was a four-team deal in which Boston sent Nomar Garciaparra to the Chicago Cubs and got back Orlando Cabrera and Doug Mientkiewicz.

But the Red Sox also swung trades for Dave Roberts and Mike Myers, which helped them pull off their unprecedented 2003 ALCS comeback against the Yankees and end their 86-year championship drought.

ASTROS RENTALS

After being traded by the Seattle Mariners, Randy Johnson went 10-1 with a 1.28 ERA in 11 starts with the Astros in 1998, but Houston was eliminated in the NLDS.

Houston got its money’s worth, too, after acquiring Carlos Beltran from the Kansas City Royals in 2004, as he tied an MLB record with eight homers that postseason.

The Astros were eliminated in the NLCS, however, and Beltran left for the Mets that winter.

CC SABATHIA, 2008

The Milwaukee Brewers went all in.

Chasing their first playoff berth since 1982, the small-market Brew Crew added Sabathia from Cleveland that July for a package of Michael Brantley, Matt LaPorta, Zach Jackson, Rob Bryson.

Despite his impending free agency, Sabathia embraced the role of workhorse, hurling 130.2 innings, including seven complete games, with a 1.65 ERA over 17 starts, including the final three on short rest.

The Brewers made the playoffs, and Sabathia parlayed his standout season into a seven-year, $161 million contract with the Yankees that winter.

MANNY RAMIREZ, 2008

Somehow, another trade in 2008 rivaled that of Sabathia’s.

Tired of their fractured relationship with Ramirez, the Red Sox traded the slugger to the Los Angeles Dodgers in a three-team deal that netted them Jason Bay and Josh Wilson.

Ramirez batted .396 with 17 homers and a 1.232 OPS in 53 games after the trade, then helped the Dodgers win a playoff series for the first time in two decades.

MARK TEIZEIRA, 2008 & 2009

Two Teixeira trades turned into franchise cornerstones.

In 2008, the Texas Rangers sent the first baseman to the Braves for Elvis Andrus, Matt Harrison and Neftali Feliz, who helped take Texas to back-to-back World Series berths in 2010 and 2011.

In 2009, the Braves traded Teixeira to the Los Angeles Angels for Casey Kotchman and Stephen Marek.

While that return was far less spectacular, the Angels received a first-round compensation pick when Teixeira left in free agency for the Yankees — which they turned into Mike Trout.

YOENIS CESPEDES, 2015

The Mets’ trade for Cespedes nearly never happened.

They originally agreed to acquire Carlos Gómez from the Brewers for a package that included Wilmer Flores, who was famously moved to tears on the field after learning of the deal.

But the Mets failed Gomez’s physical, then pivoted to another outfielder in Cespedes.

Cespedes hit 17 homers in 57 games, then helped lead the Mets to the World Series.

He signed multiple contracts with the Mets from there, including a four-year, $110 million deal before the 2017 season that did not go as well.

PETE CROW-ARMSTRONG, 2021

Conversely, the Mets made a regrettable move in 2021 when they traded Crow-Armstrong, then a 19-year-old prospect, to the Cubs for Javier Baez.

Baez played well after the trade, hitting .299 in 47 games, but the Mets missed the playoffs, and he left in free agency that winter.

Crow-Armstrong, meanwhile, is currently in the middle of a breakout season and, at age 23, is a legitimate NL MVP candidate.

JUAN SOTO, 2022

Any time a player of Soto’s stature gets traded is notable.

But what makes this deal so notable is what the Washington Nationals received in return.

Knowing they would be unable to extend Soto, the Nats traded him to the San Diego Padres for a five-prospect package headlined by James Wood, MacKenzie Gore and C.J. Abrams.

Abrams was an All-Star in 2024, while Wood and Gore were both All-Stars this year. None is older than 26 or eligible for free agency before 2028.

This is the modern-day standard for a trade deadline haul.

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