Greatest MLB Trade Deadline Deals of All Time

These MLB trade deadline moves changed the entire baseball landscape — and the course of history.

Major League Baseball’s trade deadline gets more attention than any other sport. A big reason for this is the consistency of the date. It used to be June 15 until 1986. Then it was always July 31. Now it can be any day between July 28 and Aug. 3.

The MLB trade deadline also generates the most action. Any team can wheel and deal. Teams either seek a missing piece to put them over the top in a pennant race or look to unload a star and replenish their farm system.

The best moves make the most impact. Some benefit teams right away. Others take a couple of years to manifest but still produce dividends. Here are the greatest trade deadline deals in MLB history.

25. Cespedes for the Rest of Us

Yoenis Cespedes bats during the first inning of a game against the Miami Marlins in 2017. Lynne Sladky / AP Photo

Year: 2015

Teams involved: New York Mets, Detroit Tigers

Trade: Yoenis Cespedes to the Mets, Michael Fulmer and Luis Cessa to the Tigers

Bottom line: Just as Reggie Jackson was “the straw that stirs the drink” for the Yankees nearly 40 years earlier, Yoenis Cespedes became the fulcrum of the crosstown Mets during their playoff push.

In 57 games with the Mets, Cespedes hit one fewer home run (17) than he hit in 102 games with the Tigers. His play helped propel the Mets to the 2015 World Series, where the team fell to the Royals.

While the Mets’ end of the trade garnered all of the headlines, the Tigers got more than an adequate return. Prospect Michael Fulmer was in the minors at the time, but he won the 2016 AL Rookie of the Year and was named an All-Star one year later.

24. Rickey Gets Another Ring

Ricky Henderson played 44 games with the Blue Jays. Ron Frehm / AP Photo

Year: 1993

Teams involved: Toronto Blue Jays, Oakland Athletics

Trade: Rickey Henderson to the Blue Jays, player to be named (Jose Herrera) and Steve Karsay to the Athletics

Bottom line: In addition to being MLB’s all-time leader in stolen bases, Rickey Henderson also had a knack for always being in the right place at the right time.

In 1989, Henderson was traded from the Yankees to the Athletics and won a World Series title with the Bash Brothers.

Four years later, Henderson was traded from the A’s to the Blue Jays and won another World Series with his new team.

The only two rings of Henderson’s historic Hall of Fame career came in years in which he was acquired in a midseason trade.

23. The Big Unit Lands in Space City

Randy Johnson throws a pitch for the Astros against the Philadelphia Phillies in 1998. Chris Gardner / AP Photo

Year: 1998

Teams involved: Houston Astros, Seattle Mariners

Trade: Randy Johnson to the Astros; Freddy Garcia, Carlos Guillen and player to be named (John Halama) to the Mariners

Bottom line: After failing to agree on a contract extension during the 1998 season, the Mariners traded Randy Johnson to the Astros just minutes before the trade deadline.

A rejuvenated Johnson looked every bit like the best pitcher on the planet as he posted a 1.28 ERA for Houston after having a 4.33 ERA for Seattle.

The Astros gave up a lot for a two-month rental of Johnson, who then departed as a free agent after the season, as pitcher Freddy Garcia and infielder Carlos Guillen went on to make a combined five All-Star games in their careers.

22. One Man’s Trash Is Another Man’s Treasure

Toronto Blue Jays third baseman Edwin Encarnacion rounds the bases after hitting a home run against the Rays in 2009. Brian Blanco / AP Photo

Year: 2004

Teams involved: Toronto Blue Jays, Cincinnati Reds

Trade: Edwin Encarnacion, Josh Roenicke and Zach Stewart to the Blue Jays; Scott Rolen to the Reds

Bottom line: The funny thing about this trade is that Edwin Encarnacion was just a throw-in on this deal. The Blue Jays really wanted the two other players included in the deal (Josh Roenicke and Zach Stewart ), and those players won 11 combined games in their MLB careers.

The Reds would only agree to the deal if they could dump Encarnacion, and they did that by trading three players for veteran Scott Rolen, who may be a Hall of Famer one day but whose best days were behind him.

Meanwhile, Encarnacion’s best days were in front of him, and he made three All-Star teams in Toronto. His 193 home runs from 2012 to 2016 ranked as the second most in all of baseball, trailing only Chris Davis.

21. A Rejuvenated Reggie in Los Angeles

Reggie Smith played 542 career games with the Dodgers and won a ring in 1981. AP Photo

Year: 1976

Teams involved: Los Angeles Dodgers, St. Louis Cardinals

Trade: Reggie Smith to the Dodgers; Joe Ferguson, Bob Detherage and Freddie Tisdale (minors) to the Cardinals

Bottom line: A career .287 hitter heading into the 1976 season, Reggie Smith batted just .218 during the first half that year. He had been struggling with a shoulder injury, but also had disputes with the Cardinals over deferred salary.

All of this added up to St. Louis being done with Smith and trading him to the Dodgers. Smith, who was raised in Los Angeles, immediately felt at home in Chavez Ravine and hit .280 with the Dodgers over the rest of the season.

He made three All-Star teams in Dodger Blue and won the 1981 World Series.

20. Red Sox Fleece the Mariners

Jason Varitek, left, congratulates Derek Lowe after a win over the A’s in 2000. Ben Margot / AP Photo

Year: 1997

Teams involved: Boston Red Sox, Seattle Mariners

Trade: Jason Varitek and Derek Lowe to the Red Sox, Heathcliff Slocumb to the Mariners

Bottom line: The Mariners thought they were just a closer away from making a pennant push in 1997, so they traded for journeyman reliever Heathcliff Slocumb. In return, Seattle gave up two young prospects, Jason Varitek and Derek Lowe.

Seattle never imagined, and Boston maybe didn’t either, that those two players would become key pieces to the Red Sox’ World Series runs. Varitek became just the fourth captain in Red Sox history on his way to winning two rings and making three All-Star games. Lowe threw a no-hitter for the Red Sox, made two All-Star teams and won a game for the team in the 2004 World Series.

Meanwhile, Slocumb struggled in Seattle and got bumped from the closer role to a middle reliever. He pitched just one-and-a-half years for the Mariners, posted a 2-9 record and had a 4.97 ERA.

19. Big Daddy to the Bronx

Cecil Fielder hit 26 home runs in 151 games with the Yankees. Dave Martin / AP Photo

Year: 1996

Teams involved: New York Yankees, Detroit Tigers

Trade: Cecil Fielder to the Yankees, Ruben Sierra and Matt Drews (minors) to the Tigers

Bottom line: From 1989 to 1991, Cecil Fielder or Ruben Sierra finished as the runner-up to the AL MVP every year. But by 1996, they were both aging sluggers and were in need of changes in scenery.

The Yankees had a sudden glut of outfielders after calling up Darryl Strawberry from the minors, so they sent Sierra to Detroit for the first baseman Fielder. “Big Daddy” was a big bat for the Yanks in their postseason push, and he smacked three home runs in the playoffs as New York won the World Series.

Meanwhile, Sierra went from the World Series winner to a team that would lose 109 games, the worst season (at that point) in the 96-year history of the Tigers.

18. The Padres Get Their Missing Piece

San Diego Padres’ Greg Vaughn connects on a 432 foot upper deck home run in the fourth inning of the Padres’ game against the New York Mets Wednesday, May 13, 1998, in San Diego. It was the 17th homerun in the history of Qualcomm Stadium to reach the second deck. Vaughn also hit a two run homer in the ninth but the Padres lost to the Mets 4-3. Lenny Ignelzi / AP Photo

Year: 1996

Teams involved: San Diego Padres, Milwaukee Brewers

Trade: Greg Vaughn and player to be named (Jerry Parent) to the Padres; Ron Villone, Marc Newfield and Bryce Florie to the Brewers

Bottom line: Greg Vaughn established himself as one of the game’s best power hitters in eight years in Milwaukee, but he never sniffed the postseason. The Padres had also missed out on the playoffs for a number of years and were in desperate need of some oomph in their lineup.

Vaughn and the Padres seemed like a perfect match, and it turns out they were. Milwaukee and San Diego consummated a deal to get the slugger to the West Coast, and Vaughn and the Padres both ended their playoff droughts in 1996.

After an injury-plagued 1997 season, they bounced back the next year. Vaughn hit a franchise-record 50 home runs, while the Padres advanced to the World Series, before falling to the Yankees.

17. Griffey Played for the White Sox!?

Ken Griffey Jr. played 41 regular-season games and three playoff contests for the White Sox. Charles Rex Arbogast / AP Photo

Year: 2008

Teams involved: Chicago White Sox, Cincinnati Reds

Trade: Ken Griffey Jr. to the White Sox, Nick Masset and Danny Richar to the Reds

Bottom line: Some trades you don’t remember, and other trades you’d rather forget. This one checks both of those boxes.

MLB fans want to remember Ken Griffey Jr. as a Mariner with a small slice of Cincinnati Red. However, Griffey did suit up for a third team in his career, spending 41 games with the White Sox to close the 2008 season.

There wasn’t much of anything notable about Griffey’s tenure on the South Side, and it just looks odd seeing him in that pinstriped uniform, but he did get a taste of the postseason in Chicago for the first time in 11 years.

16. No More No-mar

Nomar Garciaparra played 105 games for the Cubs. Brian Kersey / AP Photo

Year: 2004

Teams involved: Chicago Cubs, Boston Red Sox, Montreal Expos, Minnesota Twins

Trade: Nomar Garciaparra and Matt Murton (both from Red Sox) to the Cubs; Orlando Cabrera (from Expos) and Doug Mientkiewicz (from Twins) to the Red Sox; Francis Beltran, Alex Gonzalez and Brendan Harris (all from Cubs) to the Expos; Justin Jones (minors, from Cubs) to the Twins

Bottom line: “Nomah” was tailor-made for Boston and was supposed to be the next all-time great in the mold of Ted Williams or Carl Yastrzemski, but age, injury, diminishing skills and contract demands led to his trade at the 2004 deadline.

The latter centered on Garciaparra wanting a comparable salary to Alex Rodriguez and Derek Jeter, who both had 10-year deals, but Boston wouldn’t give in to Garciaparra’s demands.

Thus, he was shipped in a four-way deal that netted Boston two former Gold Glove winners, Doug Mientkiewicz and Orlando Cabrera, both of whom became integral pieces of the 2004 World Series-winning team.

15. Miller Time in Cleveland

Andrew Miller posted a 2.20 ERA in 120 games with the Indians. Eric Christian Smith / AP Photo

Year: 2016

Teams involved: Cleveland Indians, New York Yankees

Trade: Andrew Miller to the Indians; Clint Frazier, Ben Heller, Justus Sheffield and J.P. Feyereisen (minors) to the Yankees

Bottom line: It’s not every day that a guy with 10 wins and 12 saves gets Cy Young award votes, but Andrew Miller was dominant during the 2016 season. The Yankees were using him as an insurance policy at closer while Aroldis Chapman was suspended, and once Chapman returned, Miller became expendable.

The Indians pounced at the opportunity to pick him up and Miller posted a 1.55 ERA in the regular season and a 1.40 ERA during the Indians’ run to the World Series, where they lost to the Cubs in seven games.

Pedro Martinez, a pretty decent pitcher in his own right, had this to say about Miller in 2016: “I have been in many postseasons and hadn’t seen anybody dominate like Andrew Miller. Not even the great Mariano Rivera I saw having as much success as Andrew Miller, overpowering hitters.”

14. Mex to the Mets

Keith Hernandez played in 880 games over seven seasons with the Mets. Amy Sancetta / AP Photo

Year: 1983

Teams involved: New York Mets, St. Louis Cardinals

Trade: Keith Hernandez to the Mets, Neil Allen and Rick Ownbey to the Cardinals

Bottom line: Despite being a five-time Gold Glove winner and batting champion for the Cardinals, Keith Hernandez never saw eye to eye with manager Whitey Herzog. The skipper even labeled Hernandez a “cancer” and gleefully shipped him to the lowly Mets in 1983.

A rejuvenated Hernandez proceeded to put in some of his best work in New York and won another six Gold Gloves.

After winning a World Series title for the Cards in 1982, “Mex” won another with the Mets in 1986.

13. Rangers Reel in a Bounty for Teixeira

Mark Teixeira hit 37 home runs with the Braves. David Kohl / AP Photo

Year: 2007

Teams involved: Texas Rangers, Atlanta Braves

Trade: Elvis Andrus, Neftali Feliz, Matt Harrison, Jarrod Saltalamacchia and Beau Jones (minors) to the Rangers, Mark Teixeira and Ron Mahay to the Braves

Bottom line: The general consensus in trades is that the team that gets the best player wins the deal. That wasn’t the case with this trade.

Mark Teixeira put up Hall of Fame numbers, but the sum of the parts that the Rangers received made them the clear winner.

The four players the Rangers received have played a combined 30 seasons with the team (and counting, since Elvis Andrus is an active player). Many of those players were core Rangers during the team’s back-to-back World Series appearances in 2010-11 and three of them made All-Star teams as Rangers.

Meanwhile, Teixiera spent just one year in Atlanta, playing in 157 games, before being traded to the Angels before the 2008 deadline.

12. Darvish the Double Agent

Yu Darvish did not help the Dodgers in the 2017 World Series. Mark J. Terrill / AP Photo

Year: 2017

Teams involved: Los Angeles Dodgers, Texas Rangers

Trade: Yu Darvish to the Dodgers; A.J. Alexy (minors), Brendon Davis (minors) and Willie Calhoun to the Rangers

Bottom line: While the Dodgers were the ones who landed a four-time All-Star ace in Yu Darvish, their opponents in the 2017 World Series benefitted the most from the trade.

Darvish was lit up in both of his World Series starts against the Astros and gave up nine earned runs in just 3.1 innings pitched for an ERA of 21.60.

After the conclusion of the World Series, an Astros player revealed that Darvish was tipping his pitches, which enabled Houston to pretty much know what he was throwing every single time.

11. A Giant Acquisition for Pence

Hunter Pence played 772 games with the Giants. Morry Gash / AP Photo

Year: 2012

Teams involved: San Francisco Giants, Philadelphia Phillies

Trade: Hunter Pence to the Giants; Tommy Joseph, Seth Rosin and Nate Schierholtz to the Phillies

Bottom line: Right field had become a carousel for the Giants during the 2012 season, and they looked for someone to solidify that position. They found that someone in a former Phillie, Hunter Pence, who was traded by the Astros just before the deadline the year prior.

Pence didn’t light the world on fire with his bat, but he was a steadying influence in the locker room and expertly patrolled AT&T Park’s unique right-field wall. Before Pence’s arrival, the Giants had a .544 win percentage. After trading for him, they had a .644 win percentage over the rest of that season.

That season also ended with a World Series championship, the Giants’ second in three seasons.

10. The Midnight Massacre

Tom Seaver felt right at home with the Reds. AP Photo

Year: 1977

Teams involved: Cincinnati Reds, New York Mets

Trade: Tom Seaver to the Reds; Doug Flynn, Steve Henderson, Dan Norman and Pat Zachry to the Mets

Bottom line: The Mets can thank sportswriter Dick Young for this trade as Young wrote a story claiming that Tom Seaver was being goaded by his wife to ask for more money from the Mets.

Upon hearing about the story, Seaver cut off contract negotiations and demanded a trade.

The Mets granted his demand in what was known as the “Midnight Massacre,” and Seaver was shipped to Cincinnati, where he added 75 wins over six seasons.

9. Indians Get Their Ace

Corey Kluber has won two Cy Young Awards with the Indians. Tony Dejak / AP Photo

Year: 2010

Teams involved: Cleveland Indians, San Diego Padres, St. Louis Cardinals

Trade: Corey Kluber (from Padres) to the Indians, Ryan Ludwick (from Cardinals) to the Padres, Jake Westbrook (from Indians) and Nick Greenwood (from Padres) to the Cardinals

Bottom line: Sometimes you just need the right system or pitching coach to reach your full potential, and Corey Kluber found that with the Indians in 2010.

Back then, he was a sub-.500 pitcher in the minors and wasn’t even among the top 30 Padres prospects. But San Diego really wanted an extra power bat in Ryan Ludwick, so Kluber was shipped out in a three-team deal.

It took two full years for Kluber to start his first MLB game, but he hasn’t looked back since then on his way to winning two Cy Young awards.

8. A ‘Dempster’ Fire of a Trade

Chicago Cubs starting pitcher Kyle Hendricks delivers against the St. Louis Cardinals in 2014. Charles Rex Arbogast / AP Photo

Year: 2012

Teams involved: Chicago Cubs, Texas Rangers

Trade: Kyle Hendricks and Christian Villanueva to the Cubs, Ryan Dempster to the Rangers

Bottom line: This is the old-proven-veteran-for-unproven-prospect trade as the Rangers traded for 35-year-old Ryan Dempster and dealt away 22-year-old Kyle Hendricks.

It’s one thing that the Rangers only got half a season out of Dempster in which he posted an ERA north of 5.00. But it’s another thing that Hendricks then developed into one of the best pitchers in all of baseball.

He led the National League in ERA in 2016, finished third in Cy Young voting and also helped end the Cubs’ World Series drought. By 2016 Dempster already was in his third year of retirement and working for the MLB Network.

7. Bobby V, Meet the Mets

New York Mets first baseman Bobby Valentine lunges to tag Cincinnati Reds batter Joe Morgan at first base in 1977. Brian Horton / AP Photo

Year: 1977

Teams involved: New York Mets, San Diego Padres

Trade: Bobby Valentine and Paul Siebert to the Mets, Dave Kingman to the Padres

Bottom line: Dave Kingman hit nearly 450 home runs in his career so he would normally be the headliner in a trade. But when he was sent to San Diego for a struggling utility infielder named Bobby Valentine, the course of Mets history changed forever.

Valentine was acquired by the Mets and made a minimal impact as a player, hitting just .222 over two seasons. But he was introduced to the franchise, and some 18 years later, he was re-introduced to the Mets fan base as their new manager.

Bobby V had his ups and downs as skipper of the Mets, but he did lead the franchise to the NL pennant in 2000, where they lost to the crosstown Yankees in the World Series.

6. The Final Piece of San Francisco’s Puzzle

Javier Lopez had a 2.47 ERA in 446 games with the Giants. Eric Risberg / AP Photo

Year: 2010

Teams involved: San Francisco Giants, Pittsburgh Pirates

Trade: Javier Lopez to the Giants, John Bowker and Joe Martinez to the Pirates

Bottom line: The role of a setup man is often overlooked. He doesn’t get wins like starters or saves like closers, and can anyone really define what a hold is?

The Giants were making their postseason push in 2010, and they knew they needed an upgrade at this important but often disregarded role, so they traded for Lopez. Not only was Lopez one of the best lefty specialists out of the bullpen, but he also had World Series experience from the 2004 Red Sox.

Lopez posted a microscopic 1.42 ERA for San Francisco in the regular season and a 1.59 ERA in the postseason. He added to his ring count with the 2010 World Series, then added a third ring two years later and a fourth ring in 2014.

5. Welcome to Mannywood

Manny Ramirez hit .322 with 44 home runs in 223 games with the Dodgers. Chris Pizzello / AP Photo

Year: 2008

Teams involved: Los Angeles Dodgers, Boston Red Sox, Pittsburgh Pirates

Trade: Manny Ramirez (from Red Sox) to the Dodgers, Jason Bay (from Pirates) to the Red Sox; Brandon Moss and Craig Hansen (both from Red Sox) and Andy LaRoche and Bryan Morris (both from Dodgers) to the Pirates

Bottom line: Not since Fernandomania in the early 1980s had one baseball player stimulated as much excitement in Los Angeles as Manny Ramirez did upon joining the Dodgers.

Ramirez batted nearly .400 during his two months in Los Angeles and finished fourth in NL MVP voting despite the limited number of games. He helped the Dodgers win their first playoff series in 20 years, and no one knew his worth to the team as much as “ManRam” did.

After the season, Ramirez became a free agent and said, “Gas is up, and so am I,” in regards to his prospective contract offers. He then re-signed with the Dodgers to provide more Mannywood moments for Los Angeles.

4. Big Mac to the Redbirds

Mark McGwire rounds the bases after hitting his 70th home run of the season in 1998. Amy Sancetta / AP Photo

Year: 1997

Teams involved: St. Louis Cardinals, Oakland Athletics

Trade: Mark McGwire to the Cardinals; Eric Ludwick, T.J. Mathews and Blake Stein to the Athletics

Bottom line: Mark McGwire was in his contract year in 1997, and after a dozen years in Oakland, the A’s knew they weren’t going to be able to re-sign him. Thus, they shipped him to his former manager, Tony LaRussa, with the Cardinals.

The Cards also were a bit pessimistic that they would re-sign McGwire, but after smacking 24 home runs in just 51 games, McGwire didn’t want to leave Busch Stadium.

He then signed a long-term deal with the Cardinals, and we all know what happened in 1998 — McGwire hit 70 home runs to break the single-season record.

3. Aaron ‘Bleepin’ Boone to the Bronx Bombers

Aaron Boone played 54 games for the Yankees. Charles Krupa / AP Photo

Year: 2003

Teams involved: New York Yankees, Cincinnati Reds

Trade: Aaron Boone to the Yankees; Brandon Claussen, Charlie Manning and cash to the Reds

Bottom line: On the same day that the Yankees shipped third baseman Robin Ventura to the Dodgers, New York traded for Aaron Boone to help fill the void at the hot corner.

Boone had a so-so regular season but then contributed one of the most famous home runs in major league history in the postseason.

During Game 7 of the 2003 ALCS, he hit a walk-off home run in the 11th inning to defeat the rival Red Sox and earn the nickname of “Aaron F—ing Boone.”

2. A ‘Steal’ of a Trade

Dave Roberts played just 45 games with the Red Sox, but he is a Boston legend. Chris Gardner / AP Photo

Year: 2004

Teams involved: Boston Red Sox, Los Angeles Dodgers

Trade: Dave Roberts to the Red Sox, Henri Stanley (minors) to the Dodgers

Bottom line: The 2004 Red Sox had just about everything a team needed, except speed. They finished 11th in stolen bases, so they sought Dave Roberts for some speed off the bench at the trade deadline.

While Roberts had 33 steals with the Dodgers, he was barely used during the regular season for Boston and had just five steals. His sixth steal came during the postseason and is one of the most famous stolen bases in major league history.

Roberts swiped second base in Game 4 of the ALCS while the Red Sox were trailing in the bottom of the ninth against the New York Yankees. He scored on a single just pitches later to even up the game and push it into extra innings where Boston prevailed.

That win kicked off the Red Sox’ historic series comeback, and Roberts finished the 2004 postseason with more stolen bases (1) than base hits (0).

1. Brock for Broglio

Lou Brock became a Hall of Famer with the Cardinals. AP Photo

Year: 1964

Teams involved: St. Louis Cardinals, Chicago Cubs

Trade: Lou Brock, Jack Spring and Paul Toth to the Cardinals; Ernie Broglio, Doug Clemens and Bobby Shantz to the Cubs

Bottom line: The Cubs loved Lou Brock’s speed, but they didn’t love his .251 batting average, so the impatient front office flipped him for pitcher Ernie Broglio. Everyone assumed that the Cubs got the better end of the deal since Broglio had led the NL in wins in 1960.

But Brock’s progression made the Cardinals the winner of the deal as he became a base-stealing demon in St. Louis. He led the NL in steals for eight seasons, reached 3,000 career hits and was inducted into the Hall of Fame on the strength of his 16 years in St. Louis.

This trade ended up so one-sided that it is on par with the infamous Herschel Walker trade in the NFL. “Brock for Broglio” has become a phrase in baseball used to signify a lopsided trade, and the trade even has its own Wikipedia page.