The Biggest Bombshells in MLB Winter Meetings History

Joel Reuter@JoelReuterBRFeatured ColumnistDecember 10, 2019

The Biggest Bombshells in MLB Winter Meetings History

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    MIKE NELSON/Getty Images

    The annual MLB winter meetings are underway as the baseball world converges on San Diego for the yearly flurry of free-agency and trade activity.

    While numerous notable moves have been made during previous winter meetings, we're going to focus on the bombshells that no one saw coming.

    What do we mean by a bombshell?

    Jon Lester's choice of the Chicago Cubs over the Boston Red Sox and San Francisco Giants in 2014 is one of the most impactful moves in winter meetings history. However, it was far from a bombshell. The Cubs were always viewed as one of the front-runners to sign him, so no one was left mouth agape when the news broke.

    Likewise, the blockbuster trades that sent Chris Sale to the Boston Red Sox and Giancarlo Stanton to the New York Yankees were landscape-altering deals, but they didn't come out of nowhere.

    On the other hand, no one expected the Los Angeles Dodgers to cut baseball's first $100 million check for Kevin Brown during the 1998 meetings or the Arizona Diamondbacks to trade No. 1 overall pick Dansby Swanson just months after drafting him.

    Now that we've clarified what is meant by bombshell, let's get to it.

Hall of Fame Slugger Traded to Orioles

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    Frank Robinson
    Frank RobinsonUncredited/Associated Press

    Date: Dec. 9, 1965

    Transaction: Baltimore Orioles acquire OF Frank Robinson from the Cincinnati Reds for SP Milt Pappas, RP Jack Baldschun and OF Dick Simpson

    As the story goes, Cincinnati Reds owner Bill DeWitt referred to Frank Robinson as "an old 30" in an effort to justify to the fanbase the decision to trade the future Hall of Famer to the Baltimore Orioles during the 1965 winter meetings.

    In his final year in Cincinnati, Robinson hit .296/.386/.540 with 33 home runs and 113 RBI in a 5.1-WAR season. He had 324 home runs and 63.9 WAR in 10 years with the Reds, earning six All-Star nods and 1961 NL MVP honors.

    His first year in Baltimore could not have gone better.

    He hit .316/.410/.637 with 49 home runs and 122 RBI to win the Triple Crown and become the first player in MLB history to win an MVP award in both leagues. He capped off the season by going 4-for-14 with two home runs in the Fall Classic to win World Series MVP honors.

    The "old" slugger played six seasons with the Orioles, posting a better OPS+ than he did in Cincinnati (169 to 150) while adding 179 home runs and 32.3 WAR to his resume.

    It goes down as one of the most lopsided trades in MLB history.

White Sox 'Open for Business'

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    Jim Kaat
    Jim KaatRon Kuntz Collection/Getty Images

    Dates: Dec. 10-12, 1975

    Traded: SP Jim Kaat (to PHI), 3B Bill Melton (to CAL), CF Ken Henderson (to ATL), RP Dan Osborn (to ATL), RP Dick Ruthven (to ATL), RP Rich Hinton (to CIN), IF Lee Richard (to STL), IF Larvell Blanks (to CLE), IF Mike Buskey (to PHI), RP Steve Dunning (to CAL), C Jeff Sovern (to CIN)

    Acquired: 1B Jim Spencer (via CAL), OF Ralph Garr (via ATL), RP Clay Carroll (via CIN), OF Buddy Bradford (via STL), UT Alan Bannister (via PHI), IF Jack Brohamer (via CLE), RP Greg Terlecky (via STL), RP Roy Thomas (via PHI), OF Morris Nettles (via CAL)

    After a 75-86 showing in 1975, and with previous owner Bill Veeck back to steer the ship, change was coming for the Chicago White Sox when the winter meetings rolled around. Joe Posnanski of Sports Illustrated told the story:

    "It was 1975, the meetings were at the Diplomat Hotel in Hollywood, Fla., and the owners had (against their better judgment—and on the second vote) allowed showman Bill Veeck to repurchase the Chicago White Sox. They were worried that Veeck, who in his previous life as an owner had sent a midget to the plate, would make a mockery of the game.

    "The next day Veeck and his general manager, Roland Hemond, set up a table and phones in the lobby of the Diplomat. And they posted a homemade sign that read: OPEN FOR BUSINESS. BY APPOINTMENT ONLY. Then Veeck and Hemond sat there for 14 straight hours and made four trades, the last one—Bee Bee Richard to St. Louis for Buddy Bradford and Greg Terlecky—just seconds before the midnight deadline. And the crowd cheered."

    Veteran ace Jim Kaat, starting third baseman Bill Melton and starting center fielder Ken Henderson were among the players the White Sox dealt. While it didn't lead to an immediate reversal of fortune, Chicago won 90 games in 1977 as first baseman Jim Spencer, shortstop Alan Bannister and left fielder Ralph Garr filled everyday roles.

A Record-Breaking 10-Year Deal

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    Dave Winfield
    Dave WinfieldFocus On Sport/Getty Images

    Date: Dec. 15, 1980

    Transaction: OF Dave Winfield signs a 10-year, $23 million deal with the New York Yankees

    $23 million might not sound like much by today's standards.

    However, when Dave Winfield inked his 10-year, $23 million deal with the New York Yankees, it represented the largest contract in professional sports history.

    While his time in the Bronx was tumultuous, to say the least, in large part because of a rocky relationship with owner George Steinbrenner, he was a consistent producer through the 1980s.

    In eight-plus seasons with the Yankeeshe missed the entire 1989 season with a back injury and was traded away in May 1990he hit .290/.356/.495 for a 134 OPS+ with 205 home runs, 818 RBI and 27.1 WAR.

    He made eight All-Star Game appearances, won five Silver Sluggers and five Gold Gloves as well as finished in the top 10 in AL MVP voting four times.

    Alas, the Yankees made the playoffs only once during his decade in pinstripes, and Winfield went just 1-for-22 during the team's 1981 World Series loss to the Los Angeles Dodgers.

Blue Jays Put Finishing Touches on a World Series Winner

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    Joe Carter
    Joe CarterRick Stewart/Getty Images

    Date: December 5, 1990

    Transaction: Toronto Blue Jays acquire 2B Roberto Alomar and OF Joe Carter from the San Diego Padres for 1B Fred McGriff and SS Tony Fernandez

    The Toronto Blue Jays finished second in the AL East in 1990 with an 86-76 record. With a solid core in place, the front office could have settled for some minor tweaks to the roster.

    Instead, the team traded its two WAR leaders among position playersfirst baseman Fred McGriff (5.2) and shortstop Tony Fernandez (4.5)to the San Diego Padres during the winter meetings.

    "Will you get home before you screw up the team any further?" Toronto general manager Pat Gillick's wife, Doris, told him when she learned of the trade, according to Tyler Kepner of the New York Times.

    To be fair, the presence of top prospect John Olerud made it easier to swallow the idea of moving McGriff, who had hit .300/.400/.530 with 35 home runs and finished 10th in AL MVP voting in 1990.

    Still, it was a bold move.

    In return, the Blue Jays acquired established slugger Joe Carter, who already had 175 career home runs, and 22-year-old Roberto Alomar, who was fresh off his first All-Star appearance.

    Both elevated their games in Toronto, playing an integral role in the team's back-to-back World Series wins in 1992 and 1993. It's fair to say those titles might not have happened without this trade.

Baseball's First $100 Million Contract

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    Kevin Brown
    Kevin BrownVincent Laforet/Getty Images

    Date: Dec. 12, 1998

    Transaction: SP Kevin Brown signs a seven-year, $105 million deal with the Los Angeles Dodgers

    When Kevin Brown hit free agency prior to the 1996 season, he signed a three-year, $12.6 million deal with the Florida Marlins that ranks among the best free-agent signings of all time.

    During that three-year span (the first two with the Marlins before they traded him to the San Diego Padres), he went 51-26 with a 2.33 ERA (172 ERA+), 1.06 WHIP and 23.5 WAR. He served as the ace of the staff for a Marlins team that won the World Series in '97 and a Padres team that captured the NL pennant in '98.

    That set him up to become the first $100 million man in MLB history.

    Former Dodgers general manager Kevin Malone told Gabriel Baumgaertner of Sports Illustrated last year:

    "Mike Piazza had just signed for $91 million in New York and Mo Vaughn signed for $80 million in Anaheim. I didn't think it was a stretch to break through this arbitrary $100 million glass ceiling. We wanted his production, his intensity and his ability to make pitchers around him better. We pushed it to the limit because we felt it was worth it."

    The deal shook the MLB landscape and ushered in a new era of megacontracts.

A 3-Team, 7-Player Blockbuster

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    Curtis Granderson
    Curtis GrandersonSeth Wenig/Associated Press

    Date: Dec. 8, 2009

    Transactions: Detroit Tigers acquire SP Max Scherzer (via ARI), OF Austin Jackson (via NYY), RP Phil Coke (via NYY) and RP Daniel Schlereth (via ARI); New York Yankees acquire OF Curtis Granderson (via DET); Arizona Diamondbacks acquire SP Edwin Jackson (via DET) and SP Ian Kennedy (via NYY)

    It's not often you see a three-team trade where everyone involved is dealing established MLB talent.

    Max Scherzer had gone 9-11 with a 4.12 ERA and 174 strikeouts in 170.1 innings as part of the Arizona Diamondbacks rotation in 2009.

    Center fielder Curtis Granderson posted a 102 OPS+ with 30 home runs and 20 steals in a 4.4-WAR season with the Detroit Tigers, while Edwin Jackson was 13-9 with a 3.62 ERA in 214 innings.

    Ian Kennedy and Austin Jackson were not significant contributors for the New York Yankees in 2009, but they were both MLB-ready young players with high ceilings.

    It would be easy to call the Tigers the big winners in hindsight thanks to Scherzer's emergence as one of baseball's best pitchers.

    However, the Yankees received 115 home runs and 15.0 WAR from Granderson in his four seasons with the team, while Kennedy served as the ace of the staff for a D-backs team that won 94 games and an NL West title in 2011.

    It could be awhile before we see another trade like this one.

The No. 1 Overall Pick Is Traded the Same Year He's Drafted

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    Dansby Swanson
    Dansby SwansonNorm Hall/Getty Images

    Date: Dec. 9, 2015

    Transaction: Arizona Diamondbacks acquire SP Shelby Miller and RP Gabe Speier from the Atlanta Braves for SS Dansby Swanson, OF Ender Inciarte and SP Aaron Blair

    The Arizona Diamondbacks selected Vanderbilt shortstop Dansby Swanson with the No. 1 overall pick in the MLB draft on June 8, 2015.

    Just 184 days later, they traded him to the Atlanta Braves.

    Never before had a No. 1 overall pick been traded in the same calendar year he was drafted, and it's something we might never see again based on how this one turned out.

    The D-backs also sent out 25-year-old outfielder Ender Inciarte, fresh off a 5.2-WAR season, and right-hander Aaron Blair, who began 2015 as the No. 40 prospect in baseball, according to Baseball America.

    In return, they received All-Star starter Shelby Miller and his three remaining years of club control.

    The 25-year-old posted a 3.02 ERA and 1.25 WHIP with 171 strikeouts in 205.1 innings in his lone season with the Braves after coming over in the deal that sent Jason Heyward to the St. Louis Cardinals.

    In three years in Arizona, Miller pitched a total of 139 innings, struggling to a 6.35 ERA and 1.68 WHIP for minus-1.2 WAR.


    All stats courtesy of Baseball Reference and FanGraphs, unless otherwise noted.