Ten years ago (if you can believe it), MLBTR standard-setter Ben Nicholson-Smith ran an awesome series looking back at the most notable deals of the prior decade. We have fallen short of the typically lofty BN-S mark, but didn’t want to pass up on an opportunity to round up the biggest swaps of the ensuing ten-year span with the new year upon us.

So, in this post we’ll categorize and cover the most notable aspects of the biggest trades of the past decade. If you want to re-live them in full, follow the links at each title.

Mammoth Contract Swaps

These deals are notable for their sheer scale, in terms of the volume of players and the dollars changing hands.

The August Coastal Blockbuster

Two behemoth teams. Mammoth contracts. This one set the course for the Dodgers and Red Sox for years to come. The Los Angeles organization fell short in the NL West in the year of the swap (2012) but has owned it ever since, with Adrian Gonzalez and Josh Beckett (less so Carl Crawford) helping to set the course. While the prospects added in return didn’t amount to much, the Red Sox used the re-set to vault into a World Series crown in 2013.

And in the ensuing years? The Hollywood Dodgers have turned into a finely tuned, disciplined machine that eschews just these kinds of deals. The Red Sox tired a bit of their own analytics and went old school for a stretch, resulting in another World Series win … followed by a step back to finish off a roller-coaster decade. After Boston’s latest leadership swap, both teams’ baseball operations departments are run by former Rays executives.

Fish Off The Hook

If the Sox have put their fans through a coaster ride, the Marlins of the past decade have been one of those stomach-churning drop towers. Long, slow buildups to an expected payoff that turns out to be disappointing … if not downright unpleasant. The late-2012 deal with the Blue Jays was emblematic. As part of part of the generally craven Marlins Park scheme, the Jeffrey Loria-owned Marlins went big in free agency but turned in a complete dud. No worries. The Jays were there to bail them out.

This deal is that actually worked quite well for the Marlins in retrospect. Their MLB roster lost many of its big names — Josh Johnson, Jose Reyes, Mark Buehrle (plus Emilio Bonifacio and John Buck) — but was also relieved of some onerous salary obligations. And the swap brought in a host of affordable, useful pieces. Every single player in this trade would ultimately be a big leaguer, in fact. None of the Marlins’ acquisitions (Henderson Alvarez, Anthony DeSclafani, Yunel Escobar, Adeiny Hechavarria, Jake Marisnick, Jeff Mathis) turned into stars, but most had productive stretches and many are still active.

Unfortunately, the Marlins never really proved capable of capitalizing on the surplus value, due in some part to ensuing trades. They immediately flipped Escobar, shipped Marisnick as part of a multi-player deal with the Astros, and sent DeSclafani out for Mat Latos. (This isn’t the last time we’ll hear from the Marlins or Latos.) The Fish also dumped Heath Bell that winter, another of the players signed the prior winter. This swap also connected to a few other memorable deals on the Toronto side. It was the precursor to the Jays’ acquisition of R.A. Dickey from the Mets later that winter (link), which cost the Toronto organization Noah Syndergaard and Travis d’Arnaud. And Reyes ended up being sent out in another highly memorable deal for Troy Tulowitzki (link).

Even Bigger Fish

Fresh off a sale of the team, the Marlins auctioned off all three of their star outfielders — Giancarlo Stanton, Marcell Ozuna, and Christian Yelich — in the 2017-18 offseason. While this list is going to focus on individual deals for the most part, it makes sense to think about this series of swaps as parts of a whole.

Any follower of the baseball hot stove will remember the Stanton trade as much or more for its build-up than its end result. The prodigious slugger held full no-trade rights, thus launching a highly unusual process in which he met in person with multiple teams (the Cardinals and Giants) before spurning them. Stanton wanted the Dodgers, but the L.A. org had already transitioned to a new-school approach and wouldn’t give up enough in prospects and/or take on enough in salary to facilitate a deal. Sensing an opportunity, the Yankees stepped in.

Once again, the Marlins may ultimately be proven wise to have moved a big contract … though again, that primarily reflects the questionable initial decision to sign it. The Miami organization was forced to eat cash (in the form of the Starlin Castro contract and $30MM in obligations that’ll be owed if Stanton doesn’t opt out next winter) to move … a mid-prime player fresh off of a National League MVP award. It’s possible the Fish will get something out of the young players acquired, Jorge Guzman and Jose Devers, and the contract flexibility is great, but this one goes down as another head-scratcher when viewed in the broadest context. (It also connects to some other major swaps, as we’ll explore below.)

From the Yanks’ side, it remains to be seen if Stanton can get back on track and deliver what the team hoped he would. He was injured for most of 2019 after a good but not great first campaign in New York. The swap installed a big salary that has impacted the future roster-building efforts of the disciplined (but still big-spending) behemoth. The Stanton pact may have tempered the team’s already less-than-robust interest in Bryce Harper and Manny Machado last winter, but didn’t stop the organization from stepping up to get the star it really wanted — Gerrit Cole — to kick off the new decade.

Somewhat surprisingly, the Miami club may have picked up its best pieces in the swap that sent Ozuna to the Cardinals. Young hurlers Sandy Alcantara and Zac Gallen have both shown early promise at the MLB level. The latter was cashed in over the trade deadline for prospect Jazz Chisholm. The third part of the return, Daniel Castano, had nice numbers last year at Double-A.

The most notable of the three swaps may end up being the Yelich disaster. This one would’ve fit in some of the other categories below, for reasons that will become obvious as you read them. Yelich has morphed from a very good hitter into an absolute monster over two seasons in Milwaukee, leading the National League in OPS with machine-like even numbers of 1.000 (2018) and 1.100 (2019). The real shame from the Marlins’ perspective is that they had the foresight to lock Yelich up to a contract that still has three affordable seasons of control remaining. The Brewers are the beneficiaries. There’s still hope that the Marlins will get some value out of the return they got for Yelich — outfielders Lewis Brinson and Monte Harrison, infielder Isan Diaz, and righty Jordan Yamamoto — but the initial returns haven’t been especially promising and certainly don’t come close to the immense surplus value created by Yelich.

Young Stars

They say there’s nothing more valuable than a mid-prime, cost-controlled star. So … what does one fetch in an active trade market?

JD From A’s To Jays

Oof. This one felt strained out of the gates and just never aged well for the A’s. Josh Donaldson reached new heights upon moving to the Jays, delivering the Toronto org huge value throughout his arbitration years. On the other side? It was a volume play with a long-term upside element, but the ledger doesn’t come close to balancing on paper. Brett Lawrie fell apart in Oakland, Kendall Graveman was a solid arm but ended up hurt, and Sean Nolin didn’t contribute much. It all hinges on Franklin Barreto, who hasn’t yet caught on in the majors but has shredded Triple-A pitching and is still just 23 years of age.

Greinke Goes North

This swap, from the very beginning of the epoch under consideration, has a better vibe for all sides. The acquisition of Zack Greinke helped the Brewers to a 96-win 2011 season. While things went south for the team in the ensuing campaign, they were able to ship him out for Jean Segura at the 2012 trade deadline. On the Royals side, while it hurt to part with their staff ace, the deal helped complete the picture for the eventual World Series-winning 2015 outfit by delivering Lorenzo Cain, Alcides Escobar, Jeremy Jeffress, and Jake Odorizzi. (Cain has since returned to the Brewers via free agency; we’ll hear more on Odorizzi below.)

Sale For Sale

There’s nothing like an unfolding Winter Meetings drama, and that’s just what we got when the White Sox decided to blow things up in the 2016-17 offseason. Deep in talks with the Nationals on Chris Sale — can you imagine the resulting rotation?!?! — the South Siders pivoted to the Red Sox when the Boston organization put some of its most valued young players on the table. The return featured two exceptional talents — Yoan Moncada (who turned in a breakout 2019) and Michael Kopech (who’s returning from Tommy John surgery) — who could lead the White Sox to greatness. Luis Alexander Basabe also remains a notable prospect on the Chicago farm. And the White Sox also got some of the players they had targeted from the Nats, including 2019 All-Star Lucas Giolito, when those two teams immediately shifted to a trade involving Adam Eaton. It was a big price, but it was essential to the Red Sox’ 2018 World Series winner.

Deadline Strikes

The summer trade period creates pressures … and often delivers high drama.

Closing The Curse

The ultimate go-for-broke move came from the 2016 Cubs. The roster was loaded but needed a finishing piece. And one was available … from an unlikely place. The Yankees weren’t even fully out of contention when they began talking with teams about their top-shelf closer, Aroldis Chapman, who had been acquired for a song prior to the season after his offseason arrest. (A reported move to the Dodgers was reportedly scuttled by that news.) Chapman helped the Cubs to the promised land before returning to the Yanks on a record-setting deal in the ensuing winter. For their trouble, the Yanks came away with franchise centerpiece Gleyber Torres (plus other pieces). Having moved Chapman, the Yanks were then able to run up the market for fellow left-handed relief ace Andrew Miller, who was spun off for a big return one week later … to the Cubbies’ eventual World Series competitors, the Indians.

August Stunner

You know never to declare the deadline dealing over until well after the expiration. We often see deals finished at the very last moment, with word only trickling out after the buzzer sounds. But that’s typically a phenomenon of the traditional July trade deadline — now the only trade deadline. In 2017, the August non-revocable waiver trade period delivered the fireworks. Veteran ace Justin Verlander seemed destined to stay put in Detroit, but last-minute scrambling — including JV’s decision to waive his no-trade protection — resulted in a deal to the Astros. The results were magical, as Verlander has found a whole second life in Houston and helped the team to a title. The Tigers seemingly did as well as could’ve been hoped at the time, but likely won’t end up being adequately compensated. It remains to be seen what they’ll end up getting from Franklin Perez, Daz Cameron, and Jake Rogers.

Dramatic Duo

What a flurry … it all began when reports emerged that the Mets were closing in on a deal to acquire Carlos Gomez from the Brewers. You’ll no doubt remember Wilmer Flores shedding tears on the field. Zack Wheeler was also reportedly in the deal, too. Then a kerfluffle involving Gomez’s medicals scuttled things. Quite an alternate history.

As it turned out, the Astros stepped in to land Gomez, which turned out to be a complete bust. The club also got Mike Fiers in the swap, but that was scant consolation given the price … a strong four-some of prospects that included current relief ace Josh Hader, starter Adrian Houser, and outfielders Brett Phillips and Domingo Santana. (At the time, the order of importance of those names was roughly the inverse.)

Meanwhile, the Mets pivoted … to some guy named Yoenis Cespedes. That swap may have delivered the Mets the 2015 pennant. It also came at what has at times seemed to be a steep price (Michael Fulmer). And it launched an ever-fascinating relationship with Cespedes, who has signed two free agent deals with the club, the latter of which was just renegotiated (with the team’s present GM and his former agent) after a bizarre injury.

Go For It

It’s always fun to see what happens when a team decides that NOW is the time to push for the prize.

The Odorizzi (?) Trade

That’s not what it was at the time, but MLBTR’s Steve Adams has quipped that’s what it’d end up being in the end. There’s some truth in it, as Jake Odorizzi is right now the highest-performing player that was involved in the December 2012 swap between the Rays and Royals. At the time? It was all about the Kansas City organization making a shocking strike for James Shields, giving up top prospect Wil Myers to secure the services of the long-excellent starter. This deal didn’t really shake out as anyone expected. And we’re still feeling the aftershocks.

The Royals did get a lot of very good innings from Shields, who helped them reach the World Series in 2014 even as he was obviously on the wane. But he was gone by the time the club won its ring in 2015 … with Wade Davis, the quiet part of the Royals’ side of the swap, pitching like an absolute maniac from the bullpen. Davis carried a 0.97 ERA in 139 1/3 innings from 2014-15. He was ultimately dealt for slugger Jorge Soler.

Myers was up and down in Tampa Bay before he was traded away in another consequential deal — the three-team arrangement that netted the Rays Trea Turner, only to see him passed along to the Nationals for Steven Souza. Odorizzi ended up being quite a valuable contributor for the Rays before he, too, was traded … in a swap that seems to have fallen flat for the TB org. The Rays also added lefty Mike Montgomery in the original deal, then swapped him out for a few useful seasons of Erasmo Ramirez.

Opening Day Eve

While Craig Kimbrel had been talked about for months by the aggressive Braves, it came as a total surprise when he was dealt to the Padres just before the start of the 2015 season. The highly unusual timing was what really made this deal stand out. The primary purpose for Atlanta was to shed the contract of Melvin Upton Jr., even if it meant giving up the homegrown relief stud and taking on the dollars owed to fellow outfielders Cameron Maybin and Carlos Quentin. Kimbrel was part of a failed San Diego win-now effort. He ended up being sent along to the Red Sox in a deal that brought the Pads Manuel Margot and others … including Logan Allen, who was ultimately a piece of last summer’s three-team swap that landed the Friars a potential eventual Margot replacement in Taylor Trammell. Back to the original deal … the Braves added a solid pitching prospect who didn’t work out (Matt Wisler) and a likely inconsequential outfield prospect (Jordan Paroubeck). But they also added the 41st pick in the 2015 draft, which turned out to be still-interesting young player Austin Riley.

Snakes Pick Up Shelby After Sell By

This deal had disaster written on it from the start, but it turned out much worse than might’ve been expected. The all-in D-Backs signed Greinke and traded for Shelby Miller with visions of a glorious rotation. But the former got off to a rough start — he ultimately redeemed himself and was sent to the Astros this past summer — and the latter completely fell to pieces. The Braves, who had picked up Miller from the Cardinals for one season of Jason Heyward, made out like bandits with two strong, controllable up-the-middle players in Dansby Swanson and Ender Inciarte. Even if Swanson hasn’t been quite as awesome as might’ve been hoped, there was a load of surplus value here for the Braves.

Beautiful Disasters

There are a host of other memorable trades that have turned into forehead smackers. Many connect up to above-featured deals. The Padres’ win-now effort in 2015 began in earnest with the disastrous acquisition of Matt Kemp and his big contract in a deal that cost Yasmani Grandal. Another player added in that push by the Friars was Shields, fresh off his time in Kansas City. That deal went south quick, but the San Diego org somehow managed not only to offload most of the salary early in the 2016 season, but also to pick up current superstar Fernando Tatis Jr. from the White Sox. Oof.

The Pirates finally went for it by dealing for Chris Archer at the 2018 deadline. What seemed like a buy-low has turned into a total wreck, as Archer has scuffled while Tyler Glasnow and Austin Meadows have soared for the Rays.

The Marlins have a few more duds on their recent resume. Further driving home the dangers of early mid-season strikes, the Fish gave up Chris Paddack for a Fernando Rodney rental. They also lucked out when they were able to un-do a portion of a seven-player deal they struck with the Padres to add Andrew Cashner and Colin Rea. Miami sent the injured Rea back to San Diego and recouped pitching prospect Luis Castillo … only to send him out in the ensuing winter for Dan Straily. Castillo is now one of the best young pitchers in baseball. Miami wasn’t alone in misjudging him; they originally got him from the Giants as part of the return for journeyman Casey McGehee.

The Reds also made out like bandits when they got Eugenio Suarez from the Tigers for Alfredo Simon. Who can forget the series of deals that left Anthony Rizzo in Chicago? The Cubs got him from the Padres for Cashner, then an elite pitching prospect, after the Friars sent Mat Latos to the Reds for a four-player package that included first bagger Yonder Alonso, the aforementioned Grandal, and hurlers Edinson Volquez and Brad Boxberger. The Cubs got even bigger value in the 2013 deadline deal that brought in buy-low hurlers Jake Arrieta and Pedro Strop from the Orioles for Steve Clevenger and a half-season of Scott Feldman.