The saga — and potential fallout — of Jonathan Singleton

July 19 2015: Astros 1st baseman Jonathan Singleton during 10 - 0 win over the Rangers at Minute Maid Park in Houston, TX.
John Rivera/Icon Sportswire

Jonathan Singleton was outrighted off the Houston Astros’ 40-man roster last week, and will return to Triple-A. It’s entirely possible he will never appear in the Major Leagues again — he hasn’t played like someone who should be, up until this point — but far stranger things have happened. Regardless of how his career ends up, however, Singleton will be talked about for years to come, either as a warning, or as something of a success story. It depends, like everything, on your perspective. 

The way MLB’s compensation system is structured is designed to mimic not only its draft structure but, if you like, our society’s aspirational meritocracy in general: You start out making very little money with very little control over where you go and what you do there, but as you distinguish yourself through success at your job and through seniority, you receive promotions, increasing both your earning potential and your job security as you do so.

There are advantages to this system — for players, it provides the opportunity to become generationally rich by being a tenured major leaguer, and morally, it resonates very strongly with very many people; for teams, it allows them to drive the costs of any individual player down at the expense of paying aging stars more money on the backend of their careers.

But it is very far from perfect. The vast majority of professional baseball players do not become major leaguers; they spend a few years in the minors and then retire to pursue other, less lucrative careers. Some stick around in the high minors for a decade or two, earning a very respectable upper middle-class living; some do even better for themselves in the Japanese and Korean professional leagues, though usually that requires at least some small success in MLB first. The order of operations is very clear; you work your way to the majors, you play there for awhile under team control, and then, if you’ve proven you’re good enough to stick around and even excel, you hit free agency — and that’s where you get paid.

So Jonathan Singleton’s 2014 contract was a shock to that system. Having only been in the majors for two days — and having been negotiating this contract concomitantly with his promotion — Singleton signed a five-year, $10 million contract, buying out the remainder of his arbitration period.

26 March 2013: Astros infielder and top prospect Jonathan Singleton (89) during the spring training game between the Houston Astros and New York Yankees at George M. Steinbrenner Field in Tampa, FL.

(Mark LoMoglio/Icon Sportswire)

Baseball, as an industry, was shocked. The Player’s Association was appalled; Singleton, they reasoned, was dealing away his vast possible future earnings in arbitration for relative peanuts now, which was not something they wished to see encouraged as a point of principle. Front offices weren’t too much happier; Singleton, they reasoned, would now be encouraged to rest on his laurels, guaranteed as he was to earn millions of dollars regardless of his performance on the field.

This spoke to each party’s central anxiety when it came to their relationship with the other. The labor union worried that a worker taking less than he could theoretically have earned — remember, in 2014 Singleton was a fairly highly-regarded prospect — would impact the future earnings of other workers, while management worried that by providing a worker financial security for his future, the Astros had removed all impetus for him to hold up his end of the bargain; that now, he would cheat them.

What the Singleton contract represented, of course, was a compromise and a gamble — two things unlikely to make either management or labor very happy, in the abstract. The Houston Astros are an organization of a size and revenue stream such that they can, on occasion, knowingly risk $10 million over five years, lose that bet, get little to nothing in return, and not have it affect baseball operations in any significant way. Teams have risked many more dollars on much more established players and seen that investment detonate in their faces. And for his part, Singleton, who at the time was making a shade over $40,000 a year in the minors, cannot be faulted for taking the deal that was offered — the problem here is in the system, which makes such wild differentiations between a major league player and a minor league player with its financial incentives.

The problem the Singleton deal represented was not a problem with Singleton or Houston, but a problem with the system itself: Given the monetary rewards for being a major leaguer, it takes extreme belief in the justness of the system’s functioning to defer that opportunity by even one day if the chance is offered. And Singleton’s lack of success, despite what those who predicted disaster from day one might tell you, did not come because he stopped showing up to work after getting his money. His lack of success came because playing major league baseball is very, very, very hard to do, and Singleton turned out to be a first baseman who could not quite hit major league pitching.

The player’s association and the league are negotiating a new collective bargaining agreement right now; there’s still hope they’ll reach an agreement that will preclude a lockout by ownership. The system, such as it is, will likely continue to stagger on. But it’s still worth looking at cases like Singleton’s — and why, regardless of his success or failure as a player, his deal drew so much concern when he made it.

After all, it’s only ten million dollars, right?

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