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Who Won the Biggest Trade Deadline Deals of the Past 10 Years?

Remember when Zack Greinke was traded to the Angels? Or CC Sabathia to the Brewers? Who won the biggest deadline deals of the past 10 years?

Midseason trades make huge news when they're completed, but their long-term ramifications are seldom clear unless one team wins the World Series or the other improves their depth for the long-term. The Dodgers appear to have won the trade that netted them Yu Darvish, but what if current prospect Willie Calhoun wins a batting title for the Rangers. What if Sonny Gray flames out in New York and Jorge Mateo anchors a new youthful surge in Oakland? Today, we look back at some of the most notable deadline deals of the last 10 years and who the real winners were.


Braves acquire: Mark Teixeira, Ron Mahay

Rangers acquire: Jarrod Saltalamacchia, Elvis Andrus, Neftali Feliz, Beau Jones and Matt Harrison 

Theft, robbery—whatever you want to call it, what the Rangers did to the Braves is stealing. While Atlanta may have won the day by netting a slugger of Teixeira's caliber, they certainly lost out in the long haul by relinquishing the guys they did. Now, not all of them panned out: Jones never made it out of the minors, and Saltalamacchia only had two decent full seasons (batting .243) in Texas before he was traded to Boston in 2010. But consider Andrus, Feliz and Harrison, a trio of All-Stars for the Rangers, all came in one fell swoop, and suddenly this trade looks a lot more lopsided than anyone could have imagined: all three made back-to-back World Series appearances with the team in 2010 and 2011, and Feliz even won AL Rookie of the Year in 2010.

Teixeira was supposed to anchor Atlanta’s lineup and lead them to postseason glory, and while he lived up to his billing (batting .317 in 54 games that season), the Braves failed to make the playoffs in 2007. They were on the same downward trajectory in 2008 … and then halfway through the year, they shipped Teixeira's bat to Los Angeles. Oh, what could have been.

Winner: Rangers


Brewers acquire: CC Sabathia

Indians acquire: Rob Bryson, Zach Jackson, Matt LaPorta and a player to be named later (Michael Brantley) 

The Brewers made this trade knowing Sabathia wouldn’t stick around Milwaukee, and they’d probably do the same thing the second time around. Sabathia was dynamic the second half of the season, compiling an 11–2 record and a 1.65 ERA. Not only that, but he lead the Brewers to the postseason for the first time in more than 25 years. And they almost got away with giving up nothing, too. LaPorta, Bryson, and Jackson were the three agreed-upon prospects headed to Cleveland, with another player to be named later on the back end. Those three players barely had an impact in Cleveland: Bryson never made it big; LaPorta spent four injury-plagued seasons with the team, never batting above .254 in a season; and Jackson only threw 63.1 innings in two years with the team, limping out of town with a 6.11 ERA.

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Then there’s Brantley, the “player to be named later” in the deal. The Indians initially called Brantley up late in the summer in 2009 only to see him safely get on base each of his first eight games. For the rest of 2009 and most of 2010, he bounced back and forth between Triple-A and the majors until he finally settled into the leadoff spot in the lineup. And then, magic. Brantley has since grown into one of Cleveland’s best players, winning the 2014 Silver Slugger Award for his prowess at the plate (he hit .327 for the season and was good for 6.8 WAR—for comparison, Buster Posey led San Francisco to the World Series that season hitting .311 with 5.3 WAR). That same season, he finished third in voting for the AL MVP Award behind Mike Trout and Victor Martínez. Brantley was a rain delay away from capturing a World Series title with the Indians last year, and if the team has any chance of getting back to that point again, he’ll be one of the men leading the charge.

Winner:Both(but the Indians in the long haul)


Phillies acquire: Cliff Lee, Ben Francisco

Indians: Jason Knapp (minors), Carlos Carrasco, Jason Donald and Lou Marson

Two Cy Young winners, from the same team, traded in back-to-back seasons? Reading that now seems ridiculous, and at the time, it was tough for Cleveland Indians fans to think otherwise. Just a year after trading Sabathia for a bundle of prospects, Cleveland did the same thing with Lee, the best pitcher in baseball in 2008. In exchange for sending Lee and Francisco to the Phillies, the Indians got back another quartet of top prospects—essentially, they thought they’d rebuilt their farm system in two swift moves.

Only that didn’t quite work out. Knapp, the centerpiece of the deal, never made it to the bigs, and Marson (and his .219 career batting average) largely was out of the league three years later. Donald was a solid utility infielder for a three seasons, rotating mostly through the middle infield positions, but he too was out of baseball by 2012. The only long-term return Cleveland got out of the deal was Carrasco. He’s been one of Cleveland’s better starting pitchers when healthy (his ERA the last four seasons has never gone above his current .389), but he missed the entire 2016 postseason with a broken bone in his hand. A bunch of darts at the board, and Carrasco is the only one who really stuck.

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For the Phillies, the swap was a no-brainer. They won the World Series the year before, and by bringing in Lee, there was a good chance to defend their championship. His arrival (along with the midseason signing of Pedro Martinez) buoyed Philadelphia’s rotation and carried the team back to the World Series. There, Lee was undoubtedly the team’s best pitcher: he went for 16 innings with an ERA of just 2.81, including a complete game win in Game 1. The Yankees (behind Sabathia, ironically) would go on to win the series in six games, but without Lee in the lineup, Philadelphia might not have been there at all. Even though he was traded the next season to Seattle, Lee’s presence the second half of the 2009 season was one of the key factors that led to their second consecutive World Series berth.

Winner: Phillies



Phillies acquire: Roy Oswalt

Astros acquire: Anthony Gose, J.A. Happ, Jonathan Villar

Oswalt was already past his prime at the time of this deal, but Philadelphia still made the deal with dreams of a third consecutive World Series appearance. The righty spent the bulk of his career with Houston, but the Astros decided to deal their ace and move into a full-fledged rebuild. Oswalt had immediate success in Philly, going 7–1 in 12 starts with a 1.74 ERA. The Phillies stormed into the postseason as the top seed in the NL before losing in the NLCS to the San Francisco Giants, who went on to win the first of their three World Series titles in a five year stretch. Oswalt finished the season with the sixth-best WAR among pitchers (6.0), and the following year was part of Philadelphia’s famous “Phantastic Phour” alongside Lee (who returned as a free agent), Cole Hamels, and Roy Halladay.

As for the Astros? They actually got solid pieces back in return ... just none that stuck around. Happ came to Houston as one of the more promising pitchers in baseball after his rookie season in 2009 nearly netted him Rookie of the Year honors. But instead of continuing that upward trajectory, he and his .484 ERA were traded to Toronto after three subpar years in Houston. Happ has rebounded well since then, even earning Cy Young votes for his 20-4 campaign in 2016.

As for the other prospects Houston brought in, they weren’t as successful. Gose never suited up in the bigs for the Astros, but his stints with Toronto and Detroit have been marred by character issues. He’s currently attempting a comeback with the Tigers, only this time as a pitcher. Villar was better, but not by much. He played occasionally for Houston and struggled offensively (.236 average over three years) until 2015, when he was traded to Milwaukee. He’s still the leadoff hitter for the Brewers and has managed to stick in the bigs for reasons beyond his bat—for example, he led the majors in stolen bases in 2016. Still, none of that was to Houston’s benefit, and so the reward for a longtime ace comes up short.

Winner: Phillies


Giants acquire: Carlos Beltran

Mets acquire: Zack Wheeler (2011)

Unlike many of the other deals on this list, the Mets didn’t get a bevy of prospects for Beltran. Instead, they went for quality over quantity, bringing in Wheeler, one of baseball’s most highly-regarded pitching prospects. For the Giants, the motivation was obvious: they were coming off a World Series win and needed an offensive boost if they had any chance of repeating. Beltran was an easy fix, an All-Star still in the prime of his career; in his 44 games in for San Francisco, he hit .323 with seven home runs and 18 RBI. In spite of all that, the Giants not only failed to repeat as world champions, but they didn’t make the postseason at all. Once the year was over, Beltran packed his bags and set off for St. Louis, his rental all for naught.

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The Mets haven’t fared much better in this trade, but it isn’t necessarily a done deal just yet. Wheeler didn’t make his pro debut until two years later, when the Mets called him up in June 2013. In his first season in the bigs, the former No. 6 overall pick went 7–5 with a 3.42 ERA in 17 starts. It was a promising start for a player tapped to help revive the franchise. The next year was Wheeler’s first full season in the bigs, and he responded with an 11-11 record in 32 starts and a 3.54 ERA. Then the injuries started. Wheeler underwent Tommy John surgery in 2015 to repair a torn UCL in his elbow, sidelining him for the next two seasons. This season marked his return to the majors, and so far he’s struggled to recapture the stuff that made him a promising prospect. His 3-7 record and 5.21 ERA have come between short stints on the DL, and while it’s possible Wheeler reemerges as the quality starter he once seemed destined to become, things aren’t looking up for the Mets right now.

Winner:Giants (but if Wheeler can get back to his pre-injury form ... then Mets)



Angels acquire Zack Greinke

Brewers acquire: Johnny Hellweg, Ariel Peña and Jean Segura 

Ah, the birth of modern-day Angels baseball. 2012 saw the team sign Albert Pujols and C.J. Wilson in the offseason before calling up a youngster named Mike Trout, who would tear through the American League en route to Rookie of the Year honors. But even all that wasn’t enough to ensure Los Angeles would make the postseason in 2012, and so at the deadline, the team flipped a trio of prospects to the Milwaukee Brewers for Greinke’s expiring deal. In theory, that should’ve been enough not just to make the playoffs but to make a postseason run… only that never happened. Greinke, who was 9–3 with a 3.44 ERA at the time of the deal, went 6–2 with a 3.53 ERA in the last few months of the season for the Angels. But an August slump dropped the team too far back in the wild card race, and after the seasons, Greinke signed across town with the Dodgers for six years and $147 million.

In return for half a season of Greinke and a spot on the couch in October, the Angels gave up three prospects. As is the trend here, not all of them worked out. Hellweg pitched in eight games in the majors and gave up 23 earned runs—he’s now out of baseball. Peña pitched in seven, and is most famous for being the only reliever in MLB history to give up three home runs on Opening Day 2016—that was his last appearance in the bigs. The only player worth anything in the trade was Segura, a rookie at the time who played one game with the Angels. He stuck around Milwaukee as the starting shortstop until 2015, when he was traded to Arizona. Last season he led the NL with 203 hits and also sported a .319 batting average—the Angels could sure use a bat like that today.

Winner: Brewers


Rangers acquire: Matt Garza and a player to be named later (Neil Ramirez)

Cubs acquire: Carl Edwards, Justin Grimm and Mike Olt 

Four years feels so long ago talking about the Chicago Cubs. Today they’re the feel-good story in sports, a lingering pleasantry even if the current season hasn’t unfolded exactly as planned. As for 2013, though? The Cubs were bad, even by Cubs standard. They lost 101 games in 2012 and weren’t faring much better the year after. Instead of risking losing Garza for nothing in free-agency, Chicago pounced on the chance to deal him for a bundle of prospects. Garza was 6–1 with a 3.71 ERA at the time of the deal, and the Rangers needed an extra arm to help propel them into the postseason. Instead of waiting on their injured starters to come back, they went for Garza. His lone season in Texas wasn’t great; he went 4–5 in 13 starts with a 4.38 ERA. On top of that, the Rangers lost their final game, a tiebreaker, and missed the postseason altogether. Soon after, Garza bolted for Milwaukee, where he has since recaptured his good form.

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In exchange, the Cubs got back several young players, a few of whom helped break their 108-year-long World Series drought in 2016. Edwards, who is still only 25, finally broke through as a regular contributor this season, and his relief work in the 10th inning of Game 7 against the Indians was crucial to Chicago’s win. Grimm, another of Chicago’s young relievers, also saw World Series action.

Olt saw a little time in the majors in 2014, but by 2015, Kris Bryant was knocking at the metaphorical third base door; his arrival, coupled with Olt’s poor offensive showing (.160 batting average in 89 games in 2014), sent the latter back to the minors. As for Ramirez, he hasn’t stuck with any one team yet, and at 28, he probably won’t. Still, two young, quality relievers on a World Series championship team definitely beats out a half-season of Garza and no postseason.

Winner: Cubs


Tigers acquire: David Price

Mariners acquire: Austin Jackson

Rays acquire: Willy Adames, Drew Smyly

Up until 2013, the majority of deals done for prospects backfired, as those talented youngsters often failed to materialize into productive major league players. That wasn’t the case for Chicago when it traded Garza, but the trend quickly returned to its norm in 2014. Some quick context: When Price was traded, he was 11-8 with a 3.11 ERA—solid numbers for sure, and definitely those that would help a contender.

That was the Tigers, who had made three consecutive ALCS appearances and were hoping for a fourth. Price arrived in Detroit to pair with Justin Verlander and Max Scherzer and give the team one of the better rotations in baseball … in theory, at least. Price was a fine addition, but his ERA jumped to 3.59 in 11 starts for Detroit—by season’s end, the Tigers lost in the ALDS and Price finished the season having pitched the most innings in baseball (248 ⅓) and the most strikeouts (271). Price hung around Detroit for half of the 2015 season and was named an All-Star for the fifth time in his career, but was traded to Toronto in July 2016.

There is still hope for some of the players the Rays got back, but the returns haven’t been immediate. The Rays traded Smyly to the Mariners, but he recently had Tommy John surgery and is out for the 2017 season. Franklin has played sparingly for a number of teams since the trade, never sticking with any due to a career .214 batting average. Perhaps the most promising of the three is Adames, who hasn’t yet made it to the bigs but is hitting .262 in Triple-A right now.

Winner: Tigers