The Best 50 Could-Have-Beens of the Yankees' Past 50 Years

https://cdn.vox-cdn.com/thumbor/ClmxsgtVGSFn-WinYZbWxZZmmDs=/0x31:1600x869/fit-in/1200x630/cdn.vox-cdn.com/uploads/chorus_asset/file/25791977/50_Best_Could_Have_Beens_copy__1_.jpg

Dan Brink

A toast to the greatest Yankees of the past 50 years who tantalized but were ultimately destined for greatness elsewhere (if anywhere).

"What will you hope to accomplish?"
"When I walk down the street, people will say, 'There goes Roy Hobbs: the best there ever was.'"

It's no mystery how The Natural became a timeless classic to baseball fans everywhere. It's more than just Robert Redford being handsome as hell while socking horsehide and Wilford Brimley looking like the most wonderfully crotchety 49-year-old you've ever seen. It's also the story of The Prospect Who Couldn't Miss somehow missing, and his eventual return to glory years later.

Everyone wants to say that they were among the first people to discover a remarkable talent like early-Natural Hobbs. And when ballplayers are teenagers or in their early twenties, it's all too easy to forecast a bright future.

"He's built like a Greek god and will become a regular 50-homer hitter."

"He's got an electric arm that can light up the radar gun while also mixing it up with a devastating breaker. This kid has a Cy Young future."

"It's only a matter of time before this guy become a World Series hero in pinstripes."

Alas, not everyone becomes an Aaron Judge, a Gerrit Cole, or a Derek Jeter. There might not be any Barbara Hershey-esque femme fatales involved in the lost legends of Yankees history (though ask an old Phillies fan about Eddie Waitkus sometime), but there are some pretty darn good stories — even if they didn't feature many happy endings for the ol' Bronx Bombers.

Over the next month and a half, the Pinstripe Alley writing staff will delve into the backgrounds and histories of 50 such players from the past 50 years of Yankees baseball who fit the mold of a classic "could-have-been." Everyone selected meets one of the following criteria:

  1. A prospect who didn't live up to his potential for one reason or another and fizzled out in pinstripes.
  2. A prospect who was traded away or released, only to flourish elsewhere and force the Bronx to rue the day he left the organization.
  3. A prospect who was traded away and might not have found the success he hoped, but still makes fans remember the talent that once made him seem so promising.

The emphasis on prospects means that the most we'll consider anyone a potential "could-have-been" if they had prospect or rookie eligibility with the Yankees. Ron Blomberg is not included because his peak hype came before the 50-year period we're inspecting (1974-2024), but he would otherwise be right up the alley. Simply being young and coming to New York from another team, however, doesn't quite hit the mark. For example, there was hope that former No. 7 overall pick Rick Cerone would be Thurman Munson's worthy successor in the 1980s. But while Cerone was 25 at the time of his trade to the Bronx, he had already played 269 games in the majors, so he will not be featured.

We also will not be including any players who were already international stars by the time they came to the Yankees. NPB sensation Hideki Irabu and Cuban icon José Contreras were simply not in the same stage of their lives when they joined the Yanks as, say, Spencer Jones or Jasson Domínguez (two active players who will not be featured). Could you have stretched the definition of a "could-have-been" to include them? Sure, but they're just not on our list since we feel that they're closer to free agent signings that went wrong.

Lastly, there's a difference between a true prospect and someone who comes up and goes gangbusters out of seemingly nowhere. All 50 players on our list were either elite prospects or players who broke through elsewhere and made the Yankees regret losing them. Kevin Maas' 1990 heater certainly fits among the most surprising seasons in Yankees history, but he doesn't make for a "could-have-been" because not much was expected in the first place.

The idea of a "could-have-been" is naturally subjective. We've done our best to lay out the eligibility for our particular exercise, and we'll maintain it throughout the process. We hope you'll enjoy this look back at the Yankees who might have found their way to Monument Park in another timeline — just not ours. Thank you!


This post will be gradually updated during the series with each named player. We're going in a roughly chronological order (not a ranking).

Otto Vélez
Rick Dempsey
Scott McGregor
Ken Clay
Gil Patterson
Jim Beattie
Willie McGee
Fred McGriff
Otis Nixon

×