Sean Pendergast

Releasing Jon Singleton Ends One Wager That Jeff Luhnow Lost

The Astros have spent the last three seasons making trades where they were on the receiving end of the biggest names in the deal, dishing out prospects by the handful along the way. However, there was a time, not all that long ago, where the shoe was on the other foot, when the Astros were dealing names like Berkman, Oswalt, Bourn, and Pence for gaggles of minor league prospects, as the franchise's rebuild was in full swing.

One of the brightest potential stars to come over in such a deal was first baseman Jon Singleton, who came over to the Astros in the 2011 trade with Philadelphia for Hunter Pence. Tuesday night, Singleton's career in the Astros' system ended ignominiously as the team released him, as first reported by's Brian McTaggart on Twitter:

Singleton, a 2009 eighth round draft pick out of Long Beach, CA, unfortunately, made more of a mark on the suspension list than he did the box score in his first couple years in the Astros system, failing a test for marijuana in June of 2012, and then failing a second test in December of that year, the latter flunked test landing him a 50 game suspension.

Heading into 2014, Singleton was the baseball definition of a "depressed asset," a fearsome power hitter who was one figurative strike away from a 100 game suspension. Analytics and wagering have a lot in common, as both are, in some sense, about probabilities and outcomes. I say that as a preface to Astros GM Jeff Luhnow's decision (which some would call a "bet," given the risky nature) to offer Singleton a guaranteed five year, $10 million deal before he'd played one game in the majors. (The deal had team options in years six, seven, and eight that could bring it to $30 million total.)

The deal, in its five year form, would essentially "buy out" Singleton's arbitration years at a cost well below what the Astros would likely have to pay if Singleton were on the big league roster in those season. The additional team options would hold off free agency for a few more years. The downside for the Astros? Well, if Singleton couldn't hit big league pitching and/or stay off the weed, it would be a $10 million bet lost.

Singleton signed the deal and made his debut on June 3, 2014, and was with the big league club for the remainder of 2014, in which he hit .168 with 13 home runs. In 2015, he began the season in Fresno in the Pacific Coast League, before eventually playing in 19 Major League games later that year. That would be the last of Singleton in MLB.

As it turns out, not only couldn't Singleton hit big league pitching, he couldn't stop smoking weed either. In January of this year, he received a 100 game suspension for his third strike on the marijuana policy. (For what it's worth, Singleton admitted that he was severely addicted to marijuana in multiple interviews, so Luhnow knew what he was dealing with when they agreed to the contract in 2014.)

This brings us back to Singleton's contract — as it turns out, Singleton's bet AGAINST his own future success was the right call for him. He will get every penny of that $10 million deal. Luhnow's m.o., especially when the team was in the rebuild phase, was to offer young, good prospects deals that would give them life changing money, but keep them off the expensive (for Jim Crane) arbitration and free agency markets. It worked great with Jose Altuve, who has been one of baseball's most underpaid players until signing his big deal this past spring.

Luhnow's approach most assuredly did NOT work with Singleton. However, I'm sure this won't stop Luhnow from trying to manage the budget in similar fashion with young prospects (despite the protestations of Bud Norris).

You win some, you lose some. On Tuesday, Jon Singleton made Luhnow eat a rare L.

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