Ranking the 7 Best Win-Win MLB Trade Deadline Deals of the Century
There’s a particular kind of optimism that blooms at the MLB trade deadline. Call it mutual delusion, call it galaxy-brained hope, but every now and then, two front offices stare across the abyss, shrug, and decide to make each other better. It's rare. Like Javier Baez laying off a pitch he likes or a legendary Rockies reliever. But it happens. And when it does, it carries an uncanny beauty.
We're here to channel that feeling and provide you with the best win-win trade deadline deals since 2000. Any swaps from late June through the August waiver deadline (until it went extinct in 2019) were up for consideration.
Factors include stretch-run and postseason impact for teams acquiring a short-term star, and long-term impact for sellers.
No, the WAR won't be even if you scrutinize the statistical balance sheets, but each club got what it wanted. Every deadline trade should aspire to be one of these deals when it grows up.
7. Victor Martinez to the Red Sox
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Boston Red Sox Received: Victor Martinez
Cleveland Guardians Received: Justin Masterson, Nick Hagadone and Bryan Price
When: July 31, 2009
In July 2009 the Red Sox would seemingly do anything to inject offense into their catcher situation, short of sacrificing a live chicken. Jason Varitek was still a serviceable veteran, but his bat had tailed off in his age-37 season, as he finished with an 80 OPS+.
So they did the logical thing and picked up as professional a hitter as it gets.
Victor Martinez split his time between first base and behind the plate, slashing .336/.405/.507 with eight home runs for a 137 OPS+ and 1.3 WAR in 56 games while pushing Boston to the playoffs. He picked up down-ballot MVP votes that season and earned a second consecutive All-Star nod the following year during a 3.4-WAR campaign.
Headlining the return package was sinkerballer Justin Masterson. The 2006 second-rounder was a workhorse from 2010 to 2013 in Cleveland, averaging 194 innings to go with a 4.05 ERA during that stretch. Masterson earned his lone All-Star nod in 2013, posting a 3.45 ERA and leading the league with three shutouts across 193 frames.
6. Yoenis Céspedes to the Mets
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New York Mets Received: Yoenis Céspedes
Detroit Tigers Received: Michael Fulmer and Luis Cessa
When: July 31, 2015
Oh, the joy that the Yoenis Céspedes-New York marriage brought us. His flashy car parade at spring training. A custom tricycle. An arrival on horseback. And one heck of a run as a 2015 deadline pickup.
The Cuban outfielder sparked the Mets on a playoff push by slashing .287/.337/.604 to go with 17 home runs and 2.0 WAR in 88 games on the way to an NL East title. While he cooled off in the playoffs, those Mets made a memorable run to the 2015 World Series, eventually falling to the Royals.
His best year in the blue and orange came the next season as he finished eighth in NL MVP voting behind a 136 OPS+ and 2.9 WAR.
Notably going the other way was a young Michael Fulmer. Sure, injuries severely diminished the career of a pitcher who looked to be a front-line starter in his early 20s. But during his age-23 and -24 seasons in 2016 and '17, Fulmer posted 9.4 WAR and a 3.45 ERA in 323.2 innings, taking home AL Rookie of the Year hardware in '16.
Not a bad return on a rental Detroit had no intention of re-signing.
5. David Justice to the Yankees
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New York Yankees Received: David Justice
Cleveland Guardians Received: Jake Westbrook, Zach Day and Ricky Ledée
When: June 29, 2000
It's not every day that you can pull a World Series hero—who, while at the tail end of his career, was averaging 3.0 WAR the previous three seasons—to plug a lineup weakness at the deadline. But that's exactly what Yankees GM Brian Cashman did when acquiring outfielder David Justice for the 2000 stretch run.
All the former Atlanta and Cleveland outfielder did was post 3.2 WAR across 78 games in pinstripes that year behind a .305/.391/.585 slash line, 20 home runs and a 145 OPS+. The then-34-year-old grabbed the ALCS MVP award that year, most notably by mashing a three-run, go-ahead homer in Game 6 against the Mariners.
On the other side, while Cleveland won 90 games in 2000, it was retooling around a younger core and attempting to shed money. In Jake Westbrook, the club picked up a rotation mainstay. At his best, the right-handed starter was more solid than spectacular, peaking with a 3.38 ERA and a 129 ERA+ over 215.2 innings to go with his lone All-Star appearance. Over nine years, Westbrook logged a 4.29 ERA in 1,119.1 frames as a durable workhorse.
4. Jazz Chisholm Jr. to the Marlins
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Miami Marlins Received: Jazz Chisholm Jr.
Arizona Diamondbacks Received: Zac Gallen
When: July 31, 2019
One-for-one prospect swaps are rare. But the Marlins and D-backs made a deal of the "wait, what?" variety when Miami dipped into its well of young starting pitchers and shipped out Gallen, a then-rookie who'd started the year with a 2.72 ERA and a 10.7 K/9 over 36.1 innings.
At the time, the Miami rotation featured 23-year-olds Sandy Alcantara and Pablo López, while Caleb Smith and Trevor Richards had also shown promise. Enter Chisholm as an investment in the lineup.
The infielder bloomed into an All-Star by 2022 with a 2.4-WAR, .860 OPS season and was an exciting bright spot until the Marlins flipped him to the Yankees in 2024—even if his media star burned a bit brighter than his actual on-field contributions.
His 2025 notwithstanding, Gallen continued that early success with Arizona. In parts of seven seasons there, he's posted three top-10 Cy Young finishes, peaking in 2022 and '23 with a 139 ERA+ over 394 innings.
While the right-hander wasn't at his best in the 2023 playoffs, he did go at least five innings in each of his six starts during the D-backs' run to the World Series.
3. Aroldis Chapman to the Cubs
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Chicago Cubs Received: Aroldis Chapman
New York Yankees Received: Gleyber Torres, Rashad Crawford, Billy McKinney and Adam Warren
When: July 25, 2016
The Cubs traded their No. 1 prospect and more while hoping for one specific October outcome. It involved a 108-year drought and a billy goat. You might have heard of it.
Viewed as a slight overpay at the time, the deal brought in flame-throwing lefty Aroldis Chapman as a replacement for closer Héctor Rondón. The incumbent had a 1.95 ERA and 18 saves at the time but didn't have the track record or provide the peace of mind that a still-prime Chapman did.
The 28-year-old Cuban locked down 16 saves across 26.2 innings with a stellar 1.01 ERA after the deal. He had his ups and downs during the Cubs' title run, famously giving up Rajai Davis' game-tying, eighth-inning home run in Game 7 of the World Series. But he also put up four saves and a 3.45 ERA as a part of one of the most memorable curse-breaking championship teams in history.
The Yankees, on the other hand, won in multiple ways. They re-signed Chapman in the offseason, bringing him back on a five-year $86 million deal. That essentially gave them a free shot at a package of prospects—with Gleyber Torres notably turning into a two-time All-Star in New York.
The middle infielder finished third in AL ROY voting in 2018 by slashing .271/.340/.480 with 24 home runs and a 122 OPS+. He followed that by hitting .278/.337/.535 with 38 home runs and a 128 OPS+. While he never quite turned into the franchise cornerstone his first two seasons indicated he could, that stretch was all gravy for the Yankees considering the price.
2. Scott Rolen to the Reds
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Cincinnati Reds Received: Scott Rolen
Toronto Blue Jays Received: Edwin Encarnación, Josh Roenicke and Zach Stewart
When: July 31, 2009
The thing about win-win trades is that they sometimes need time, and 200 home runs, to bloom.
Because when the Blue Jays shipped out future Hall of Fame third baseman Scott Rolen for Encarnación and change, the latter had been benched and booed for not hustling and defensive struggles at the hot corner.
Eight seasons, five top-20 MVP finishes, three All-Star appearances and 239 home runs later, the Jays had uncovered a foundational piece in their pair of ALCS runs in 2014 and '15.
It's easy to see the Reds' side of it. They needed a veteran presence to supplement a young core led by Joey Votto. Rolen had some juice left, peaking with 4.1 WAR to go with a Gold Glove and an All-Star appearance (his first of two with the club) in 2010. His .854 OPS helped drive Cincy to 90-plus wins and an NL Central title, rounding off a Hall of Fame career.
1. CC Sabathia to the Brewers
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Milwaukee Brewers Received: CC Sabathia
Cleveland Guardians Received: Michael Brantley (as a player to be named later), Rob Bryson (minors), Zach Jackson and Matt LaPorta
When: July 7, 2008
If some win-wins need 200 homers to bloom, others need the ultimate lottery ticket known as a player to be named later. Because while ace lefty CC Sabathia was busy becoming perhaps the greatest rental addition ever in pitching the Brewers in to the playoffs, future Cleveland mainstay Michael Brantley hadn't even swapped laundry yet.
The young outfielder moved to his new digs in October of '08. By then Sabathia posted a 1.65 ERA over 130.2 innings to go 11-2 down the stretch—when such artifacts as pitcher wins impressed voters—finishing fifth in the NL Cy Young race despite just three months in the Senior Circuit.
A textbook example of a player who belongs in the Hall of Very Good, the oft-injured Brantley was a five-time All-Star in 10 seasons for Cleveland, peaking with an imposing 7.0-WAR season in 2014 when he posted a 148 OPS+ to grab a Silver Slugger award and third-place MVP finish.
Those '08 Brewers fell to the eventual champion Phillies in the NLDS, with Sabathia skipping town for New York the next offseason, but the memories from the big lefty's magical run do a lot to counterbalance the loss of Brantley's long-term impact.
Trade information and statistics via Baseball Reference unless otherwise noted.
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