The 10 biggest Deadline deals of the decade

Midseason blockbuster deals reshaped clubs and pennant races

December 3rd, 2019

Will Leitch took an in-depth look at the game in 2019 with a series exploring Major League Baseball's Data Decade. From the best World Series, to the best starting pitchers and more, Leitch ranked, dissected and celebrated all the things we loved most about the Great American Pastime during the past 10 years.

The strangest thing about going back and looking at old Deadline trades is how poorly most of them age. It might seem odd to you that, at one point of human history, the entire baseball world was turned upside down by a trade involving Jake Peavy, but I swear, it was. In looking at the biggest Deadline trades of this decade, we tried to balance both the ultimate importance of the trade and the massive splash it made the time it was made. But when in doubt, we went with the biggest splash. That’s what’s fun about the Deadline, after all.

Now, we rank the biggest Deadline month trades this decade.

1. July 30, 2015: LHP David Price goes from the Tigers to the Blue Jays for LHP Daniel Norris, LHP Jairo Labourt and LHP Matthew Boyd

It is difficult to overstate how much everyone wanted Price at the 2015 Deadline, and that the Blue Jays, a long-suffering team that hadn’t made the playoffs in more than 20 years, went out and did it, was tremendously exciting. They also traded for Troy Tulowitzki, and the results were immediate and overwhelming; seven games out of first at the time of the trade, they went 41-18 the rest of the season and won the American League East.

They ultimately bowed out in the AL Championship Series against the Royals, partly because, if you’ll remember, they were using Price out of the bullpen. But this remains the ultimate “all-chips-in” trade. Also look at the Minor Leaguer involved whom you didn’t even think about at the time: Matthew Boyd!

2. July 25, 2016: LHP Aroldis Chapman goes from the Yankees to the Cubs for RHP Adam Warren, SS Gleyber Torres, OF Billy McKinney and OF Rashad Crawford

After reaching the National League Championship Series the year before, the Cubs were clearly all-in for 2016, but trading for Chapman, the game’s most dominant reliever, made it clear how serious they were about ending the Curse: Aroldis Chapman Serious. Chapman was a huge part of the Cubs’ run to the World Series, though manager Joe Maddon rode him so hard that he was out of gas come Game 7 of the World Series, when he gave up that game-tying homer to Rajai Davis. That made it so Mike Montgomery made the final out of history, but the Cubs wouldn’t have been there without Chapman. And now look: The Yankees have Chapman back and Torres -- the key to the original trade -- to boot.

3. July 31, 2014: LHP Jon Lester and OF Jonny Gomes go from the Red Sox to the A’s for OF Yoenis Cespedes

Such is the specter of Cespedes that he was involved in two of the biggest Deadline trades of the decade. He was on the non-contender part here, with World Series hero Lester heading West as the A’s tried to take advantage of one of their best opportunities to win a World Series. It didn’t end up happening, and the Red Sox would end up trading Cespedes to Detroit a few months later. But Lester was a grand A’s moonshot taken at the perfect time. It just didn’t work out.

4. July 9, 2010: LHP Cliff Lee and RHP Mark Lowe go from the Mariners to the Rangers for 1B Justin Smoak, RHP Blake Beavan, RHP Josh Lueke and IF Matthew Lawson

Lee was the lustful object of Yankees fans for years, and that the Rangers sneaked in and got him, mostly by dangling top power prospect Smoak, would burn the britches of Bronx fans for most of the next decade. It showed that Texas meant business, and even though he wasn’t fantastic for his short stint with the Rangers, he was brilliant in the playoffs and helped get Texas to its first World Series. Then he went to Philadelphia the next year. The Yanks never did get him.

5. July 31, 2015: OF Yoenis Cespedes goes from the Tigers to the Mets for RHP Michael Fulmer and RHP Luis Cessa

Coming mere minutes before the Deadline elapsed, the Mets went for it at the 2015 Deadline, getting the slugger they felt they needed to go along with all their dominant rotation pieces. Cespedes was an instant superstar in New York, hitting 17 homers in August and September and helping the team to its first World Series in 15 years. He did so well that the Mets really had no choice but to sign him to a long-term deal that offseason (and then another one the next winter when he opted out of the first one). It didn’t turn out well … but it’s not like Michael Fulmer has been exactly what the Tigers had hoped for either.

After winning the AL Rookie of the Year Award in 2016, Fulmer has been hampered by a series of injuries, and he is recovering from Tommy John surgery, which will keep him out of action into the middle of next season.

6. July 27, 2011: Cardinals trade OF Colby Rasmus, RHP P.J. Walters, RHP Trever Miller and LHP Brian Tallet in a three-team deal and receive LHP Marc Rzepczynski, RHP Octavio Dotel and RHP Edwin Jackson

This was universally considered a horrific trade for the Cardinals at the time; ESPN’s Keith Law saw it as manager Tony La Russa forcing out a valuable young player he disliked. He wasn’t necessarily wrong, but boy did it turn out perfect for the Cards. Jackson was a rotation mainstay, and Rzepczynski and Dotel immediately shored up a faulty bullpen that St. Louis would, somehow, ride all the way to a World Series victory in La Russa’s final game as manager. And Rasmus ended up frustrating a lot more managers than just La Russa.

7. July 31, 2017: RHP Yu Darvish traded from Rangers to Dodgers for OF Willie Calhoun, RHP A.J. Alexy and IF Brendon Davis

Darvish was the subject of a good old-fashioned bidding war, and one that ensured that the Dodgers were tired of just winning the division every year and were aiming for their first World Series in nearly 30 years. Darvish felt almost like overkill when the Dodgers made the deal, but it helped take them to that Series … but his struggles in that same series were one of the main reasons they lost it.

8. July 31, 2012: OF Hunter Pence traded from Phillies to Giants for OF Nate Schierholtz, C Tommy Joseph and RHP Seth Rosin

Pence had become too expensive for a Phillies team that was about to face a roster reckoning, but he became an instant ignitor for the Giants, a team he would end up winning two World Series championships with, starting that October.

9. July 26, 2015: RHP Johnny Cueto traded from Reds to Royals for LHP Brandon Finnegan, LHP John Lamb and LHP Cody Reed

The Royals had fallen just short the season before and felt they needed some extra starting pitching oomph to reach the final frontier. Cueto struggled in the regular season for Kansas City, but he was brilliant when it counted, tossing a complete game in a 7-1 World Series Game 2 victory over the Mets. He’d ultimately earn a ring.

10. July 31, 2018: RHP Chris Archer traded from Rays to Pirates for OF Austin Meadows, RHP Tyler Glasnow and a player to be named later (RHP Shane Baz)

Obviously, it’s a little early for this one, but the ripple effects are still being felt a year later. Archer, who many thought would finally blossom in Pittsburgh, has struggled mightily for the Pirates. But Meadows and Glasnow have been key cogs of a Rays team that seems ticketed for the playoffs in 2019, though an arm injury may prematurely end Glasnow’s breakout year. It was an excellent day for Tampa Bay: The Rays picked up Tommy Pham in a deal with the Cardinals that day, too.