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Best MLB trade deadline deals of all-time

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Every year, MLB teams make deals at the trade deadline that they hope will end up making a difference, either in the immediate future or in the long run. Of course, at the time, we have no idea how these will pan out. Sometimes, what we thought we the biggest trades at the deadline turn out to be duds while deals that didn’t look like they would move the needle much ended up being huge trades. In fact, some of the best MLB trade deadline deals of all time didn’t seem that important at the time.

Best MLB Trade Deadline Deals

Naturally, it’s a lot easier to pick out the biggest trades at the deadline with hindsight.

That’s why we went through the history books to find the best MLB trade deadline deals ever made. While this is open to interpretation, here are what we believe are the most impactful deadline deals in MLB history.

Fred McGriff to Braves, 1993

Looking for a spark at the deadline in 1993, the Braves sent Vince Moore, Melvin Nieves, and Donnie Elliott to the Padres for McGriff. The acquisition of McGriff signaled the end of Sid Bream’s time as Atlanta’s first baseman, which was a big deal at the time.


However, McGriff worked out wonderfully, going to the All-Star Game three times as a member of the Braves while also helping Atlanta win the 1995 World Series and having some of the best seasons of his career with the Braves.

Derek Lowe and Jason Varitek to Red Sox, 1997

With the Red Sox out of contention in 1997, they sent Heathcliff Slocumb to the Mariners, receiving Derek Lowe and Jason Varitek in return.

They didn’t know it at the time, but it would be a transformative trade for Boston. Varitek would become one of the most important catchers in franchise history, helping the Sox win championships in 2004 and 2007. Lowe also had some good seasons in Boston and was part of the team that broke the curse in 2004.

Mark McGwire to Cardinals, 1997

After trading for McGwire in 1997, the Cardinals convinced him to sign a long-term deal to stay in St. Louis.

Then came the 1998 season, which will forever be remembered by baseball fans. That was the year that McGwire and Sammy Sosa captivated baseball with their chase of the single-season home-run record.


We know now that both players got a little outside help, but that was still a magical year for baseball fans.

Steve Pearce to Red Sox, 2018

A few days before the deadline in 2018, the Blue Jays sent Pearce to Boston for $1.5 million and Santiago Espinal.

At the time, he seemed like a modest trade to improve Boston’s bench. But Pearce came alive during the World Series, hitting three home runs against the Dodgers and being named World Series MVP as the Red Sox won another championship.

Johnny Cueto to Royals, 2015

The Royals took a chance in 2015 by trading for Cueto, who would sign with the Giants the following offseason.

He made just 13 starts with Kansas City during the regular season, posting a 4.76 ERA. But after falling short in the postseason the previous year, Cueto made all of the difference for the Royals in October. He won two of the four games he started in the playoffs, including a complete game in Game 2 of the World Series to give the Royals a 2-0 series lead on their way to a championship.

Yoenis Cespedes to Mets, 2015

The Mets may have lost the 2015 World Series, but there’s no way they get there without Cespedes.

Granted, they gave up Michael Fulmer, who eventually won Rookie of the Year with Detroit, but Cespedes was worth it. He hit 17 home runs in just 57 games with the Mets, jump-starting their offense down the stretch and propelling them to the World Series.

Curt Schilling to Diamondbacks, 2000

The D’Backs traded for Schilling in 2000, although the trade paid off the following year when he won 22 games and pitched to a 2.98 ERA.

He was even better in the postseason, going 4-0 with a 1.12 ERA. He and Randy Johnson were magnificent, sharing World Series MVP honors as Arizona beat the Yankees in the 2001 Fall Classic.

Carlos Beltran to Astros, 2004

Beltran had started to blossom into a star late in his time with the Royals, but he took things to another level after being traded to Houston at the deadline in 2004.

He hit 23 home runs and posted a .926 OPS after the trade and then put up crazy numbers during the postseason, batting .435 with an OPS of 1.557 over 12 games. Of course, he didn’t help the Astros win the World Series that year, although he did return to Houston in 2017 when the club allegedly cheated their way to a championship.

David Justice to Yankees, 2000

Eager for a third straight World Series title, the Yankees sacrificed Ricky Ledee, Zach Day, and Jake Westbrook in order to acquire Justice at the deadline in 2000.

Justice wasn’t the team’s first choice at the time, but he turned out to be the right choice. He hit .305 with 20 home runs for the Yankees in 78 games. Justice then won ALCS MVP honors, playing a pivotal role in helping the Yankees complete their three-peat of World Series crowns.

Lou Brock to Cardinals, 1964

Trading Brock to the rival Cardinals at the 1964 deadline is exactly why it took the Cubs over a century to win a World Series.

In their defense, Brock wasn’t that good of a player when he was in Chicago. However, he was immediately great after going to St. Louis, hitting .348 with 33 stolen bases for the Cardinals during the second half of the season, ultimately helping the Cards win the World Series.

Brock would go on to be a six-time all-star and lead the National League in stolen bases eight times while in St. Louis. More importantly, he helped the Cards win another World Series in 1967 and ended up being a first-ballot Hall of Famer.

Jeff Bagwell to Astros, 1990

Bagwell is perhaps the best example of a team winning a trade by getting a little-known prospect in return.

Houston sent the Red Sox reliever Larry Andersen and got Bagwell in return. For what it’s worth, the Red Sox won the AL East but got swept by the A’s in the ALCS.

Andersen then signed elsewhere that winter. Meanwhile, Bagwell blossomed into a star who won Rookie of the Year in 1991 and MVP in 1994, ultimately becoming Houston’s everyday first baseman for more than a decade and going into the Hall of Fame.

CC Sabathia to Brewers, 2008

If you want to see a player carry a team on his back, just look at what Sabathia did for the Brewers in 2008.

Milwaukee traded Michael Brantley, Matt LaPorta, Zach Jackson, and Rob Bryson to Cleveland so that Sabathia could make 17 starts for them.

But in those 17 starts, he was 11-2 with a 1.65 ERA. Seven of those 17 starts were complete games, including three shutouts. Sabathia made three straight starts on short rest to close out the regular season and carry the Brewers to the playoffs.

Unfortunately, his start in the NLDS on short rest didn’t go well. But Sabathia accomplished something incredible in those 17 starts for the Brewers before signing a big contract with the Yankees.

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