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How other teams’ hesitancy to spend led to Derek Jeter becoming a Yankee

The Yankees chose Jeter with the sixth overall pick in the 1992 MLB Draft, and it wasn’t a slam-dunk that they’d get him.

New York Yankees

A little over three decades ago, the Yankees were doing something rather rare for this organization, picking pretty high in the MLB Draft — the sixth overall spot, to be specific. With their choice, the team selected the first high schooler off the board, a shortstop by the name of Derek Jeter, and the rest was history.

Jeter went on to become The Face of the Yankees of our generation, winning a boatload of individual accolades, and enough World Series to form a modern-day dynasty.

The MLB Draft is a particular kind of crapshoot; it’s just the way the sport works. That’s not to discount any of the incredibly hard work that’s put in by everyone who’s a part of the process. It’s just that the success rate is very small, much like the one of actually hitting a baseball, kind of fitting for the sport.

So much could have happened in that Draft to change the outcome of history, it’s an odd exercise to look back at a decision that could’ve just easily gone a different direction, and all that it would’ve changed.

However, there’s a lot to uncover and discuss, that’s as far from random as it can possibly be. Deliberate choices were made, with short-sighted objectives, which ultimately led to the legend of No. 2 in pinstripes.

Houston, Cleveland, Montreal, Baltimore, and Cincinnati each held the first five picks in that year’s MLB Draft. There’s definitely a universe where Jeter becomes an All-Star for one of those other ballclubs, perhaps giving the city a championship or two, as well (something that none of the latter four has achieved since then unless you count Montreal moving to DC). But the name of the game was all about signing bonus demands.

The Astros were coming off a Draft in 1991 in which the team failed to sign its top pick, unable to meet the demands of University of Florida pitcher John Burke (the No. 6 overall pick). The organization was not about to repeat that same debacle.

Jeffrey Hammonds, an outfielder out of Stanford, and Derek Jeter, a shortstop who had received a scholarship to play for the Michigan Wolverines, both were known to command large signing bonuses. Instead, Houston chose to draft Phil Nevin, a third baseman out of Cal State Fullerton (and future Angels manager).

Chicago White Sox v Detriot Tigers
Houston didn’t even hang on to Nevin for long, trading him to Detroit in 1995.
Photo by Mitchell Layton/Getty Images

The Astros knew they were going to be able to sign Nevin for a bonus well under previous years’ No. 1 overall picks, such as Chipper Jones and Brien Taylor, ultimately settling at $700K.

There is even a newspaper clip in the Google Archives with a funny quote from Nevin:

“I realize the Houston Astros aren’t the Oakland A’s, New York Yankees, or the Toronto Blue Jays. I just think we’ll settle on something fair.”

It’s interesting to reminisce on a time in which the Athletics were big spenders (as they were while winning three consecutive AL pennants from 1988-90), and the Astros were the penny-pinchers. That’s baseball history for you.

The Astros opted for the short-sighted route, saving a few bucks, and many fans already know the story about scout Hal Newhouser (a Hall of Famer himself) quitting the team after he wasn’t able to convince the front office to sign Jeter.

Hammonds would slide all the way to the fourth pick, despite being the preferred choice of at least one of the top three teams, because of his bonus demands. Jeter fell all the way to the sixth slot, where the Yankees’ front office was only too happy to snatch him up.

Here we are talking about teams being reluctant to spend, and what else is new. However, part of what accentuated this phenomenon in the top of the ‘92 MLB Draft, was that the top four teams held the four lowest payrolls in baseball at the time. Cleveland, Houston, and Montreal in particular stood out. Their combined payroll was only marginally higher than the Yankees’ $35 million, and at the time, the Yanks weren’t even head and shoulders above the pack, slotting in as the sixth-highest payroll in the sport.

While it was reasonable to expect that those four top teams would be stingy about splashing out the cash for the top prospects, the Reds — who came in with the fifth pick — held a payroll virtually equal to the Yankees.

Cincinnati could’ve very well made the investment required to sign Derek Jeter, and yet they chose to draft an outfielder out of Central Florida, Chad Mottola. Their area scout, Gene Bennett, had urged them to take Jeter, but perhaps the organization felt that shortstop wasn’t a concern because they had Hall of Famer Barry Larkin manning the position. It’s not as though it would have been impossible for Jeter to find another home eventually if they didn’t want to move Larkin. The No. 5 overall pick Mottola received by far the lowest signing bonus out of the top six, signing for $400,000 on Draft Day.

It took a little bit of convincing, but the Yankees ultimately drafted Jeter. They got him on board for the same $700,000 that the Astros used to sign Nevin. Of course, said convincing might have ended up being more difficult for teams other than the Yankees, and there is an alternate dimension where Jeter elects to play at Michigan for a little while instead. Regardless, none of those five teams chose to pick Jeter, forgoing the chance to sign USA Today’s High School Player of the Year.

It’s never just one thing, and a wide range of factors — from luck to more deliberate choices — led the most successful organization in the sport to its greatest shortstop, and a staple of many championship teams.