Who won these past Winter Meetings blockbusters?

December 1st, 2023

The baseball world will descend on Nashville next week with the 2023 Winter Meetings set to kick off on Sunday.

Some of the biggest trades involving prospect hauls have taken place in past Winter Meetings deals, and there is plenty to keep an eye out for this year, with several clubs equipped with prospects to trade. But while we wait to see what happens this year, Jim Callis and Jonathan Mayo take a look back at some of the most famous (and infamous in the case of some organizations) blockbuster deals that have occurred at the Winter Meetings and determine the winners and losers of those transactions.

Here is a look at six of the most popular Winter Meetings -- or "Winter Meetings-adjacent" -- trades involving top prospects at the time and which side won them.

Dec. 6, 1989: Cleveland gets Sandy Alomar, Carlos Baerga and Chris James from the Padres for Joe Carter

Callis: Sandy Alomar was Baseball America’s Minor League player of the year in 1989, but he was blocked by Benito Santiago, and Baerga was regarded as a prospect, but he wasn’t your classic second base prospect. And back then RBIs were king and Joe Carter was Mr. RBI. That was a blockbuster and Cleveland won that trade because they got several years of cost control and quality play from Alomar and Baerga.

Mayo: Nowadays no one would even blink with Baerga playing second base, especially with all the shifting, but even without it. He could really hit, and Alomar and Baerga were keys to that team that had postseason success in the coming years.

Winner: Cleveland

Dec. 9, 2012: Rays get Wil Myers, Jake Odorizzi, Mike Montgomery and Patrick Leonard from the Royals for James Shields and Wade Davis

Myers was the No. 3 overall prospect on the Pipeline list, but this deal was also exciting because Montgomery was our No. 31 prospect in 2012 and Odorizzi was No. 47 that year.

Callis: I think the Rays got a decent package of talent, but I don’t think that any of those individual guys lived up to what they thought they would be, and at the time (Royals GM) Dayton Moore got killed for this trade. James Shields helped the Royals win the 2014 AL pennant … and they didn’t just get "Big Game James", they got Wade Davis, who wound up being one of the best closers in baseball and played a key role in the 2015 World Series championship and two pennants.

Mayo: I would go Royals as well. None of those guys were huge impact players with the Rays, so I will give the Royals the edge in getting Big Game James.

Winner: Royals

Dec. 9, 2015: Braves get Dansby Swanson, Aaron Blair and Ender Inciarte from the D-backs for Shelby Miller and Gabe Speier

Callis: That was one that we were all puzzled about at the time. But John Coppolella did a lot of good work in Atlanta, and I know it didn’t end well, but he did some good work in Atlanta that wound up resulting in a World Series championship.

Mayo: The Braves.

Winner: Braves

Dec. 6, 2016: White Sox get Yoán Moncada, Michael Kopech, Luis Alexander Basabe and Victor Diaz from the Red Sox for Chris Sale

Moncada was the No. 1 prospect in baseball at the time, and it marked the first time in 25 years the No. 1 guy had been included in a trade. The flame-throwing Kopech was also a Top 100 prospect.

Callis: I don’t think Moncada and Kopech have been really what the White Sox had hoped, except maybe in flashes. So, I think it’s a clear Red Sox win with a chance to maybe get more even, but I think the Red Sox make that trade every time.

Mayo: I think you cold make an argument in either direction, but the fact that the Red Sox won the World Series in 2018, and what Chris Sale has done for the Red Sox, obviously I would give the Red Sox the win even if Moncada and Kopech help the White Sox reach the postseason a few years later.

Winner: Red Sox

Dec. 7, 2016: White Sox get Lucas Giolito, Reynaldo López and Dane Dunning from the Nationals for Adam Eaton

Callis: At the time we had Giolito as the best pitching prospect in baseball and we kind of found out after that trade and into the next season that the industry had cooled on him ... I don’t know if (Nationals GM) Mike Rizzo would admit this now, but I think the Nationals thought they were selling high on Lucas Giolito at the time.

Mayo: Even if Lucas Giolito has been a little up-and-down, he has been a mainstay in the White Sox rotation, and Adam Eaton … I remember thinking at the time, 'Wow! They got all of that for Adam Eaton?' And I still think, 'Wow! They got all of that for Adam Eaton?'

Winner: White Sox

Dec. 3, 2018: Mariners get Jarred Kelenic, Jay Bruce, Anthony Swarzak, Justin Dunn and Gerson Bautista from the Mets for Robinson Canó and Edwin Díaz

Callis: It’s really flipped, hasn’t it? At first we’re like, what a bad trade for the Mets. And now it’s like, what’s going on with Jarred Kelenic? Are the Mariners going to get anything out of this?

Mayo: Justin Dunn has since moved on, and say what you want about Robinson Canó but Edwin Díaz has turned into Edwin Díaz, so check mark for the Mets, unexpectedly. Which is why you can’t really evaluate things like this until much later on because you never know. Not that Edwin Díaz was a throw-in, but complementary pieces and not the big names end up being the best players in trades.

Winner: Mets