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Lead Deals at Winter Meetings

12:05AM UTC

Baseball lands in San Diego next week, with the 2022 Winter Conference kicking off Sunday.

Some of the largest deals involving potential clients occurred in past winter conference deals , while lining up to follow suit this year, Jim Callis and Jonathan Mayo got together on the Pipeline podcast to review some of the most famous (and, in some organizations, notorious) blockbuster deals that took place at the Winter Conference and identify their winners and losers.

Here are six of the most popular winter conferences — or “adjacent” “Winter Meetings” — deals at the time involving top prospects and which side won.

December. 6th, 1989: Cleveland trades to Padres for Joe Carter


Sandy A Lomar was the Minor League Player of the Year in 1989, but he was blocked by Benito Santiago, and Belga was considered a prospect, but he wasn’t your typical second base rookie. Back then RBI was king and Joe Carter was Mr. RBI. It was a blockbuster, and Cleveland won the deal because they got several years of cost containment and quality play from Alomar and Baerga.


Now nobody is going to blink to see Baerga come in second base, especially with all the shift, but even without it. He can really hit the ball, and Alomar and Baerga are the keys to this team’s postseason success for years to come.

December-September 2012: Thunder acquire Will Myers, Jake Odoriz, Mike Montgomery and Patrick Leonard from Royals for James Shields and Wade Davis

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


I think the Rays have pretty decent talent, but I don’t think either of these guys survived until what they thought they were going to be, At the time (Royals general manager) Dayton Moore was killed because of the trade. James Shields helped the Royals win the 2014 AL pennant…not only did they get “Big Game James,” they got Wade Davis, who would eventually become baseball’s One of the best finishers and played a key role in the 2015 World Series championship and two pennants.


I’m going to the Royals too. None of these guys are huge impact players for the Rays, so I’d give the Royals an edge in getting Big Game James.

Dec-September 2015: Warriors acquire Dansby Swanson, Aaron Blair and Ender Inciarte from D-backs for Shelby Miller and Gabe Speier

Callis: That was a question that confused us all at the time. But John Coppleira did a lot of good things in Atlanta, and I know it didn’t end well, but he did some good things in Atlanta and ended up with a World Series title.

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 top rookie in baseball at the time, which marks 25 For the first time in years a No. 1 has been included in the deal. Flame-breathing Kopech is also a top-100 prospect.


I don’t think Moncada and Kopech are really what the White Sox are hoping for, other than maybe in a flash. So, I think it’s a clear Red Sox win with a chance for more, but I think the Red Sox will trade every time.


I think you’re arguing in either direction, but the fact that the Red Sox won the World Series in 2018, and Chris Sale for the Red Sox With everything the team has done, obviously even with Moncada and Kopech helping the White Sox, I’m going to get the Red Sox into the playoffs after a few years of winning.

December. 7, 2016: White Sox acquire Lucas Giolito, Reynaldo Lopez and Dane Dunning from Nationals for Adam Eaton


At that time we had Giolito as the best pitching prospect in baseball, we found the industry after the trade and next season Cooled him off…I don’t know if (Nationals general manager) Mike Rizzo would admit it now, but I think the Nationals thought they were sold high on Lucas Giolito at the time.


Even though Lucas Giolito has been a bit of an up and down guy, he’s been the mainstay of the White Sox rotation, and Adam Eaton… I remember thinking, ‘Wow! They got all of that for Adam Eaton? I still think, ‘Wow! They got all that for Adam Eaton? ‘

December. March 2018: Mariners acquire Jarred Kelenic, Jay Bruce, Anthony Swarzak, Justin Dunn and Gerson Bautista from Mets for Robinson Canó and Edwin Díaz


Really flipped, didn’t it? At first we thought, what a bad deal this is for the Mets. Now it’s like, what happened to Jarred Kelenic? Will the sailors get anything out of it?


Justin Dunn has moved on since then, say what you will about Robinson Canó, but Edwin Díaz becomes Edwin Díaz, so surprisingly for the Mets tick. 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 rather than big names ended up being the best player in the deal.

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