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Here are 10 big swaps made well before Trade Deadline

July 15th, 2023

Every year, we see a flurry of activity in the hours leading up to the Trade Deadline, but sometimes the biggest moves are made weeks before that, with savvy front offices striking early to improve their teams.

The benefit is obvious. Adding a player two or three weeks early can make a considerable difference in a postseason race.

Here are 10 blockbuster trades from this century that were consummated at least 10 days before the Trade Deadline, starting with the most recent. The 2023 Deadline is set for Aug. 1 at 6 p.m. ET.

Dodgers acquire 3B/SS Manny Machado from Orioles
Date: July 18, 2018
Orioles receive: OF Yusniel Diaz, IF Rylan Bannon, RHP Dean Kremer, RHP Zach Pop, IF Breyvic Valera

In World Series-or-bust mode after losing to the Astros in the 2017 Fall Classic, the Dodgers sent five players to the O’s for Machado one day after the 2018 All-Star Game. Machado was worth 2.4 Wins Above Replacement in 66 games with Los Angeles, per FanGraphs, and the club won the National League pennant for the second straight year. However, the slugger struck out swinging against Chris Sale for the final out of the World Series and finished the postseason with a .672 OPS before signing a 10-year, $300 million contract with the Padres the following February. Of the players the Orioles received in the trade, only Kremer is still with the organization.

Yankees acquire 3B Todd Frazier, RHP David Robertson, RHP Tommy Kahnle from White Sox
Date: July 19, 2017
White Sox receive: RHP Tyler Clippard, OF Blake Rutherford, LHP Ian Clarkin, OF Tito Polo

This trade worked out well for the Yankees, with Kahnle and Robertson combining to toss 5 2/3 scoreless innings in the Yanks' 2017 AL Wild Card Game victory over the Twins and 24 1/3 effective frames (3.33 ERA) altogether during the postseason that year. Frazier, meanwhile, became a positive clubhouse presence and hit a key three-run homer in Game 3 of the 2017 AL Championship Series with the Yankees trailing the Astros two games to none.

D-backs acquire OF J.D. Martinez from Tigers
Date: July 18, 2017
Tigers receive: 2B Dawel Lugo, SS/2B Sergio Alcantara, SS/2B Jose King

While Martinez spent just a few months with the D-backs before signing with the Red Sox the next February, Arizona easily won this deal. Martinez produced 29 homers with 65 RBIs in only 62 games with the D-backs, helping the club reach the postseason for the first time since 2011 and ensuring the 2017 National League Wild Card Game was played at Chase Field rather than Coors Field.

Nationals acquire LHP Sean Doolittle, RHP Ryan Madson from A's
Date: July 16, 2017
A's receive: RHP Blake Treinen, LHP Jesús Luzardo, 3B Sheldon Neuse

The Nationals addressed a weak spot by adding Doolittle and Madson to their bullpen during the 2017 season, and Doolittle turned in an All-Star campaign in 2018 before helping the Nats win the World Series the following year. Treinen was also excellent for Oakland in 2018, finishing sixth in the AL Cy Young race after posting a 0.78 ERA over 80 1/3 innings. He signed with the Dodgers in free agency after the 2019 campaign. The A's ended up trading Luzardo to the Marlins for veteran outfielder Starling Marte at the 2021 Trade Deadline.

Cubs acquire LHP José Quintana from White Sox
Date: July 13, 2017
White Sox receive: OF Eloy Jiménez, RHP Dylan Cease, 2B Bryant Flete, 3B Matt Rose

The Cubs were gaining control of Quintana for three-plus years at the time of the trade, and as a result they paid a steep price to bring him to the North Side of Chicago just two days after the 2017 All-Star Game. Quintana ended up recording a 4.24 ERA over 82 games (78 starts) in a Cubs uniform. Meanwhile, the Cubs watched Jiménez and Cease become key members of the White Sox young core.

A's acquire RHP Jeff Samardzija, RHP Jason Hammel from Cubs
Date: July 5, 2014
Cubs receive: SS Addison Russell, RHP Dan Straily, OF Billy McKinney, cash

Samardzija was famously shipped to the A's shortly before the 2014 All-Star Game, leading to the right-hander being introduced with the National League while wearing a generic All-Star Game cap. Samardzija continued to excel after the trade and Hammel was serviceable, helping Oakland claim the second AL Wild Card spot by one game over the Mariners. After Oakland lost the AL Wild Card Game to the Royals, Samardzija was sent to the White Sox in a deal that landed the A's Marcus Semien, and Hammel re-signed with the Cubs. The Cubs later flipped Straily and McKinney in deals for Dexter Fowler and Aroldis Chapman, respectively, and those two joined Russell in helping the club win the 2016 World Series championship.

Brewers acquire RHP Francisco Rodriguez from Mets
Date: July 12, 2011
Mets receive: LHP Danny Herrera, RHP Adrian Rosario

Looking to bolster its bullpen for the stretch run, Milwaukee picked up Rodriguez from the Mets on the same day as the 2011 All-Star Game. K-Rod pitched like an All-Star the rest of the way, recording a 1.86 ERA and giving Milwaukee a dominant setup man in front of closer John Axford. The Brewers were tied with the Cardinals in the NL Central when Rodriguez was acquired, but the right-hander helped the club win the division by six games. Herrera posted a 1.13 ERA over 16 games for the Mets in 2011, but he didn't appear in the Majors thereafter, and Rosario never pitched in a Major League game.

Rangers acquire LHP Cliff Lee, RHP Mark Lowe from Mariners
Date: July 9, 2010
Mariners receive: 1B Justin Smoak, RHP Josh Lueke, 2B Matt Lawson, RHP Blake Beavan

The Lee deal was a major success for the Rangers, who made the first of their two straight World Series appearances in 2010 with help from the southpaw's 2.78 ERA in 35 2/3 innings during the postseason. The trade also kept Lee away from the Yankees, who went on to lose to Texas in the 2010 ALCS. Although Lee left to sign with the Phillies in the following offseason, only one of the players the Rangers surrendered in the trade -- Smoak -- did anything of note in the Majors, and that came years later with the Blue Jays.

Cubs acquire RHP Rich Harden, RHP Chad Gaudin from A's
Date: July 8, 2008
A's receive: 3B Josh Donaldson, RHP Sean Gallagher, OF Matt Murton, OF Eric Patterson

Harden enjoyed one of the best stretches of his career after the trade, recording a 1.77 ERA in 12 starts with the Cubs, who won the NL Central that year. The right-hander posted a 4.09 ERA in 26 starts for the Cubs the next season before hitting free agency and signing with the Rangers. But Donaldson, then a catching prospect in the low Minors, ultimately emerged as the best player from this trade. The third baseman finished among the top eight in AL MVP Award voting in both 2013 and 2014, helping the A's make the postseason in both years. He was then traded to the Blue Jays for a four-player package that included Franklin Barreto and Kendall Graveman.

Brewers acquire LHP CC Sabathia from Cleveland
Date: July 7, 2008
Indians receive: OF Michael Brantley, 1B Matt LaPorta, RHP Rob Bryson, LHP Zach Jackson

Although he signed with the Yankees after the 2008 season, Sabathia is arguably one of the greatest Trade Deadline acquisitions ever, as he put the Brewers on his back and carried them to the third postseason appearance in franchise history. Despite making only 17 starts for Milwaukee, the big left-hander finished fifth in '08 NL Cy Young Award voting after going 11-2 with a 1.65 ERA and seven complete games. The Brewers were behind the Cardinals in the NL Wild Card race when Sabathia was acquired but ended up winning it by a game over the Mets, 3 1/2 games over the Astros and four games over the Cardinals. LaPorta was supposed to be the big prize on Cleveland's end of the deal, but Brantley -- the player to be named later in the trade -- became a three-time All-Star (2014, 2017, 2018) for the club before signing with the Astros in December 2018.