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Cubs history: The time they almost traded for Derek Jeter

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That could have affected the fortunes of two franchises.

Imagine this guy in blue pinstripes instead of navy... it almost happened
Photo by Al Bello/Getty Images

Max Rieper runs our SB Nation Royals site Royals Review, but that site and the Kansas City Royals have nothing to do with this article.

But I owe Max a debt of gratitude for finding this gem, a clip from a Sporting News article from 1994:

Well now. That would have changed up Cubs history just a bit, no?

Derek Jeter was the Yankees’ first-round pick in the 1992 draft (sixth overall). In mid-season 1994 he was on a path from Advanced-A through Double-A. He eventually played Triple-A ball in 1994 and debuted for the Yankees May 29, 1995. Overall at three levels in 1994 he hit .344/.410/.463 with five home runs, 50 stolen bases in 58 attempts and scored 103 runs.

The Cubs had a succession of players start at shortstop in the mid to late 1990s, including Rey Sanchez, Jeff Blauser, Jose Hernandez, Alex Gonzalez and Shawon Dunston. Dunston, who had been the starter for nearly a decade, left via free agency after 1995, which would have been the perfect time for Jeter to take over. With Jeter at shortstop, the Cubs might have gone further in the 1998 postseason and who knows, might have wound up making more postseasons than they did.

Pat Kelly was a nothing-special utility guy. The clip there doesn’t say who the third player in the deal would have been, likely a prospect, as the 1994 Yankees didn’t have a lot of young players in the major leagues. But that Yankee team was in position to make a World Series run; they “finished” first in the A.L. East that year, “finished” in quotes because the strike ended the season and who knows where they’d have wound up, though their 70-43 record was best in the A.L. at the time. They hadn’t made the postseason since 1981 and the following year, they’d begin a run of 17 postseason appearances in 18 years, which included six World Series appearances and four WS titles.

Randy Myers pitched one more year for the Cubs and then also left after 1995 via free agency. Having Derek Jeter around from the beginning of his career would have been much, much better. And while the Yankees might still have been a playoff-caliber team in the Jeter era, the Cubs might have been right there with them in the postseason.