4 Derek Jeter Trades That Would've Shifted the Entire MLB Landscape

Jacob Shafer@@jacobshaferFeatured ColumnistJune 3, 2020

4 Derek Jeter Trades That Would've Shifted the Entire MLB Landscape

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    Today, Derek Jeter is the face of the Miami Marlins ownership group and guiding the franchise through a painful rebuild.

    He's also a Hall of Fame shortstop who staked his place among the all-time New York Yankees greats during his 20-year career in pinstripes.

    Here's an interesting thought experiment: What if the Yanks had dealt Jeter before he became a franchise icon?

    Believe it or not, credible trade chatter surrounded The Captain before he made his New York debut. Let's take those old rumors, plus a dollop of our own what-if speculation, and see what would have happened to the MLB landscape if he had wound up in a different uniform.

Scenario No. 1: Jeter to the Chicago Cubs

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    In 1994, a strike cut the season short in August. It cost baseball dearly as the World Series was canceled, and fans responded with extreme ire.

    The strike also might have prevented a Jeter-to-the-Chicago Cubs swap.

    According to a report from Sporting News (h/t Max Rieper of Bleed Cubbie Blue), the Cubs believed they had a deal in the works to send left-handed reliever Randy Myers to the Yankees in exchange for second baseman Pat Kelly and then-prospect Jeter, plus an unnamed third player.

    The impending work stoppage made teams hold back at the July trade deadline. But had this deal gone through, it would have been a massive coup for the Cubbies.

    After he was selected by New York with the sixth overall pick in the 1992 amateur draft, Jeter hit .344 with an .873 OPS between High-A, Double-A and Triple-A in 1994 and made his big league debut the following year. 

    He would have joined a Cubs team that was mired in last place in the National League Central when the '94 campaign ended but returned to the postseason as a wild card in 1998.

    Jeter obviously would have been a pivotal part of Chicago's resurgence and could have accelerated its championship-drought-busting timeline.

    The Yankees, meanwhile, could have landed Myers, a solid bullpen arm who made three All-Star appearances between 1994 and 1997 but was out of the league following the 1998 season.

    All it would have cost them was a franchise shortstop who became one of the most beloved players in club history.

Scenario No. 2: Jeter to the San Francisco Giants

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    This one requires some serious speculation, but bear with us.

    If we assume, based on the Sporting News report, that the Yankees were open to dealing Jeter, the San Francisco Giants could have been a fit.

    By 1993, Brian Sabean was working in the Giants' front office, and in 1996, he was promoted to general manager. Prior to that, he worked as a scout in the Yankees organization and was heavily involved in the decision to draft Jeter.

    Before the 1997 season, Sabean remade San Francisco's roster, most notably trading All-Star third baseman Matt Williams to the Cleveland Indians for a package of players that included second baseman Jeff Kent.

    In a different world, Sabean could have dangled Williams to the Yankees. New York's primary third baseman in '97 was veteran Charlie Hayes, who posted a modest .728 OPS in 100 games that season. Needless to say, Williams, who swatted 32 homers with 105 RBI for Cleveland, would have been a significant power upgrade.

    In the spring of '96, with Jeter struggling in spring training, the Yankees reportedly considered a trade for Seattle Mariners shortstop Felix Fermin that would have included Mariano Rivera.

    "They had Felix Fermin they wanted to move,'' Yankees general manager Brian Cashman recalled, per Newsday's Erik Boland. "They wanted either Mariano Rivera or Bob Wickman. One of those two guys for Felix Fermin, and The Boss [owner George Steinbrenner] was honestly considering it and forced us to have some serious conversations about it."

    Rivera on the Mariners would have created an alternate reality that would have worked out decidedly well for Seattle.

    Jeter, meanwhile, if blocked by Fermin, could have joined a Giants lineup that included Barry Bonds and won the NL West title in Sabean's first year at the helm. He would have doubtlessly helped the Giants compete during Bonds' prodigious prime.

    Another note: Jeter would have likely blocked shortstop Rich Aurilia, who was the Giants' Opening Day starter at the position every season from 1998 to 2003 and hit 37 home runs in 2001.

Scenario No. 3: Jeter to the Los Angeles Dodgers

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    In a world in which the Giants went after Jeter, it's easy to imagine the archrival Los Angeles Dodgers getting involved.

    Again, we're purely in the realm of speculation. But the Dodgers cycled through an array of middling veterans at shortstop from the mid-'90s well into the 2000s and could have benefited from a rising star such as Jeter. 

    It's impossible to say what, exactly, the Yankees would have demanded in return. But the Dodgers' roster and pockets were deep (sound familiar?). They employed five consecutive National League Rookie of the Year winners between 1992 and 1996 and could have put together a better package than the one the Cubs reportedly offered.

    Again, assuming the Fermin deal went through, the Yanks might have been open to a swap. And Jeter would have landed in another huge market where his abilities and marketable personality would have played well.

    And given the fact he won five rings with New York while developing a reputation as a clutch performer in big moments, he might have helped Los Angeles win its first title since 1988.

Scenario No. 4: Jeter to the Montreal Expos

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    In 1999, the Montreal Expos made a play for Jeter under owner Jeffrey Loria. Nick Cafardo of the Boston Globe offered the details:

    "When Jeffrey Loria owned the Expos, he was obsessed with Derek Jeter. So he ordered his general manager, Jim Beattie, to try to make a deal with the Yankees and to give up whatever he had to. Beattie offered Yankees GM Brian Cashman Vladimir Guerrero and Pedro Martinez. Stunned, Cashman told Beattie, 'I can't trade Derek Jeter.'"

    That is an incredible what-if.

    First off, Jeter would have joined an Expos team that Loria would later sell before it relocated to Washington D.C. and became the Nationals prior to the 2005 season. Perhaps a player of Jeter's quality could have altered that trajectory, or maybe he would have been another star caught in the series of fire sales Loria oversaw during his time as owner of the Expos and, later, the Marlins.

    On the other side of the deal, the Yankees would have landed a pair of future Hall of Famers.

    Over the course of their distinguished careers, Guerrero and Martinez posted WARs of 59.5 and 86.1, respectively, and both would surely have thrived under the bright lights of Yankee Stadium. Plus, the Yanks could have kept Pedro away from the Boston Red Sox, with whom he won a Curse-of-the-Bambino-busting ring in 2004.

    Would it have been worth sacrificing Jeter and his 71.3 career WAR? We'll never know, but it sure is a fascinating hypothetical.


    All statistics courtesy of Baseball Reference.