The baseball world will descend on San Diego next week with the 2022 Winter Meetings set to begin on Sunday.
Here’s a look at six of the most popular Winter Meetings — or “adjacent Winter Meetings” — trades involving the top prospects at the time and which side won them.
December 6, 1989: Cleveland trades 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 considered 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 blink with Baerga playing second base, especially with all the moves, but even without him. He could really hit, and Alomar and Baerga were the keys to that team having postseason success in years to come.
December 9, 2012: Rays acquire Wil Myers, Jake Odorizzi, Mike Montgomery and Patrick Leonard from 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 any of those individual guys lived up to what they thought they would be, and then (Royals GM) Dayton Moore got killed for this trade . James Shields helped the Royals win the 2014 AL pennant … and not only did they get “Big Game James,” they got Wade Davis, who ended up being one of the best closers in baseball and played a key role in the World Series of -2015. championship and two pennants.
Mayo: I used to go to Royals too. Neither of those guys were huge impact players with the Rays, so I’m going to give the edge to the Royals to get Big Game James.
December 9, 2015: Braves acquire Dansby Swanson, Aaron Blair and Ender Inciarte from D-back for Shelby Miller and Gabe Speier
Callis: That was one we were all confused 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 ended up resulting in a World Series championship.
December 6, 2016: White Sox acquire Yoán Moncada, Michael Kopech, Luis Alexander Basabe and Victor Diaz from Red Sox for Chris Sale
Moncada was the No. 1 prospect in baseball at the time, marking the first time in 25 years that the No. 1 guy had been included in a trade. The flamethrowing Kopech was also a Top 100 prospect.
Callis: I don’t think Moncada and Kopech were really what the White Sox had hoped for, except maybe in flashes. So, I think it’s a clear Red Sox win with a chance to maybe get even more, but I think the Red Sox make that trade every time.
Mayo: I think you’re cold making an argument either way, but the fact that the Red Sox won the World Series in 2018, and what Chris Sale did for the Red Sox, of course I’d give the Red Sox the win even if Moncada and Kopech help the White Sox reach the postseason a few years later.
December 7, 2016: White Sox acquire 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 found out after that trade and the next season that the industry was going cold on him … I don’t know if (Nationals GM) Mike Rizzo wouldn’t admit it now, but I think the Nationals thought they were selling Lucas Giolito high at the time.
Mayo: Even though Lucas Giolito was a little up and down, he was a mainstay in the White Sox rotation, and Adam Eaton… I remember thinking at the time, ‘Wow! Did they get all that for Adam Eaton?’ And I’m still thinking, ‘Wow! Did they get all that for Adam Eaton?’
December 3, 2018: Mariners acquire Jarred Kelenic, Jay Bruce, Anthony Swarzak, Justin Dunn and Gerson Bautista from the Mets for Robinson Canó and Edwin Díaz
Callis: It’s really crazy, isn’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? Will the Mariners get anything out of this?
Mayo: Justin Dunn has since moved on, and say what you will about Robinson Canó but Edwin Díaz turned into Edwin Díaz, so check out for the Mets, unexpectedly. That’s why you can’t really evaluate things like this until much later 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 the trade.