Sep 7, 2021 4 min read

The time Derek Jeter could've become a Chicago Cub

The time Derek Jeter could've become a Chicago Cub

A trade rumor in 1994 had the future Yankees legend landing on the North Side.

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When Derek Jeter is inducted into Baseball's Hall of Fame today, he'll become the 54th one-franchise member in Cooperstown.

But what if he were going in as a Cub after a short stint with a team out east. You know, Ryne Sandberg style?

That alternate timeline could have started in 1994, at least according to one long-forgotten rumor that circulated that summer.

The trade? The Cubs would've sent closer Randy Myers to the Yankees for a package that included Jeter, who was still only 20 at the time.

For whatever it's worth, then-Yankees GM Gene Michael vehemently denied the report at the time.

"That's not even close," Michael said. "From what our people say about Jeter, absolutely not."

But would Michael have felt differently had an inescapable labor stoppage not been looming?

Michael died in 2017 and it's unlikely he would've ever copped to even briefly considering the idea after watching the career that Jeter turned in.

But consider this: In 1994, the Yankees were in the 13th year of a playoff drought and still under the control of the ever-impatient George Steinbrenner. They took over first place in the AL East in early May and had built a 6.5-game lead over Baltimore at the time of the strike with an AL-best 70-43 record.

With Mariano Rivera's own Hall of Fame career still a year away from starting, the Yankees bullpen was led that year by Steve Howe. The 36-year-old was in the middle of his last great season with a sub 2.00 ERA and 15 saves. Still, Howe's history of drug use and suspensions didn't exactly instill any confidence for helping out Don Mattingly in what would've been his first postseason appearance.

Enter Myers, who had saved a best-in-baseball 53 games for the 1993 Cubs and was in the middle of his age 31 season. He'd save an NL-best 38 games again in 1995 (though that year was best remembered for the "It's Gonna Happen" fan running on the field to confront him after Myers gave up a big homer in late September).

The No. 6 overall pick in the 1992 draft, Jeter was considered the jewel of the Yankees farm system at the time and had recently been elevated to Double-A. A promotion to the Bronx, where he'd replace names like Mike Gallego and Tony Fernandez, seemed imminent.

Trading away a cornerstone shortstop for a closer in order for just a chance at breaking a drought seems incomprehensible now, but ...

  • It was 1994. Prospects weren't viewed as untouchable as there are now. Even Michael's view on Jeter seems like it was informed by what his "people" were telling him second-hand. It's not that hard to picture Michael trading away Jeter to satisfy a Steinbrenner whim.
  • The Cubs pulled the opposite of this trade almost 20 years later, sending Gleyber Torres to the Yankees for Aroldis Chapman in their successful bid for the 2016 World Series title.

So it probably wasn't totally out of the question. Jeter's quick ascendance to the top of the Yankees franchise, where he'd stay for almost the next two decades, only makes it seem that way.

Jeter would only play a total of five games at Wrigley during his career, going 5-for-22 with five singles and no extra-base hits.

The what-if questions that remain are fun to think about.

Do the Cubs end their World Series drought earlier if Jeter plays on the North Side? Do the Yankees win their last five World Series titles without him? How would Jeter have gotten along with Sammy Sosa  during the boombox years? Would Jeter have turned the double play that Alex Gonzalez couldn't?

The answers are out there somewhere in the Cubs' multiverse.

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