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Best Trades Ever At Winter Meetings?

Elliott Price
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Best Trades Ever At Winter Meetings?

The first baseball convention was way back in 1857. The winter meetings became an annual event in 1900. It’s hard to believe any trade or signing had quite the impact of the Orioles/Reds trade of 1965. The deal turned out to be a huge mistake for Cincinnati.

Reds general manager Bill Dewitt believed former MVP Frank Robinson was past his prime at age 30. He thought the outfielder’s talent was fading due to leg injuries. Orioles executive Lee MacPhail thought different.

MacPhail sent the Reds pitchers Jack Baldschun and Milt Pappas plus outfielder Dick Simpson for Robinson and changed the course of baseball history and the Baltimore Orioles forever.

Robinson won the triple crown in 1966, leading the O’s to their first world series championship while winning his second MVP. The first to win MVP in both leagues. With Robinson the Orioles made it back to the fall classic three times in six years, winning it a second time in 1970.

It wasn’t the first time a future MVP was aquired at the meetings. Before the 1960 season Kansas City traded Roger Maris to the Yankees. He  eventually won two MVP awards, hitting a record sixty-one homers and winning two world series in the Bronx.

Who Had Best Winter Meetings Ever?
Mickey Mantle and Yankees teammate Roger Maris after a home run in 1961, Yankee Stadium IMAGO/Pond5 images

Let’s not forget that the Yankees brought an even better hitting right fielder home from the meetings last year when they grabbed the last year of Juan Soto’s contract. He came along with Trent Grisham for Michael King, Drew Thorpe, Jhony Brito, Randy Vásquez and Kyle Higashioka.

Tigers grab two future hall of famers

Best Winter Meetings Trades Ever?
Detroit Tigers DH Miguel Cabrera waves to fans after making his last play at first base as a Tigear Sunday, Oct. 1, 2024 – Credit: © Kirthmon F. Dozier / USA TODAY NETWORK

You’ve got to hand it to Dave Dombrowki who in 2007 and 2009 traded for a pair of future hall of famers. First Miguel Cabrera from Miami along with pitcher Dontrelle Willis for six players including Andrew Miller and Cameron Maybin.

Two years later it was a wild three team deal – The Top players involved – The D-backs received Edwin Jackson and Ian Kennedy, The Yankees, Curtis Granderson. The Tigers won this one easily. They landed Max Scherzer.

Saddest trade for a franchise?

Best Winter Meetings Trades Ever?
June 1981; Cincinnati, OH, USA; Montreal Expos catcher Gary Carter at Riverfront Stadium – Mandatory Credit: Malcolm Emmons-Imagn Images

Montreal Expos owner Charles Bronfman regretted the changing tides of baseball’s finances. In particular the seven year $14 million extention for catcher Gary Carter signed prior to the 1982 season. New general manager Murray Cook was told to trade him.

Prior to the 1985 season he was off to the Mets where he would win a world series in 1986. In exchange for Carter, New York gave up Hubie Brooks, Mike Fitzgerald, Herm Winningham and Floyd Youmans.

Blue Jays-Padres blockbuster

This 1990 trade involved four all stars and three future hall of famers. Blue Jays general manager Pat Gillick helped pave his way to Cooperstown with this risky deal. The Jays sent two very popular players to San Diego, shipping Fred McGriff and Tony Fernandez out West.

MLB — Toronto Blue Jay Joe Carter watches the world series winning homerun – Credit IMAGO / Newscom World – Date 22.10.1993

In return the Padres furnished the Blue Jays with a walkoff world series homer hero in Joe Carter and a twenty-one year old second baseman and future hall of famer in Roberto Alomar. The Jays would win back to back series with the pair in ’92 and ’93.

More MVPs and hall of famers

The trading of greatness at the winter meeting hasn’t abated over the years. Rickey Henderson joined Gary Carter being traded in 1984 as he went from the Athletics to the Yankees.

Then back to back years in 2016 and 2017 saw Chris Sale go from White to Red Sox and reigning NL MVP Giancarlo Stanton got shipped from Miami to the Bronx.

From the exploits of the Padres ‘Trader Jack’ McKeon to the Cardinals Whitey Herzog putting together the 1980’s Cardinals, you can almost always expect something to pop at the meetings.

As baseball brass from every team settle in Dallas, trades will be one thing. Free agency another and that probably means a new home for supertar Juan Soto before they leave there. Should be a fun few days as the winter hot stove is turned up to eleven.

About the author

Elliott Price

Elliott Price

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Elliott spent more than 40 years in sports broadcasting. He hosted sports morning shows in both Montreal and Toronto. Elliott handled play by play duties in a multitude of sports. Most notably as the voice of the Montreal Expos. Also CFL football, NHL hockey, OHL and QMJHL junior hockey, boxing, soccer, swimming and more. He currently is senior baseball writer for 'The Sports Rush'

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