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Astros reportedly lock up Jon Singleton, make a fantastic deal

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It's a fantastic deal for them. Probably not for Singleton.

Tommy Gilligan-USA TODAY Sports

When Gregory Polanco spurned the Pirates' contract advances, we looked at the performance of top-10 hitting prospects to see which side might have gotten the better of the deal. Thanks to Jon Singleton and the Houston Astros, we have another fascinating contract to discuss. Singleton received five guaranteed years at $10 million, with three team option years after that.

If you assume close-to-the minimum salaries for the first three years and standard regular-player raises after that, it's not out of the question that Singleton would have made close to $10 million for his first five years. In exchange for the guaranteed cash, though, Singleton was willing to trade in two of his free-agent years.

As a man with 84,392 Monty Fariss rookie cards, I understand the temptation to get the guaranteed payday before playing in a major-league game. As someone who writes about baseball contracts all the time, I understand why some people are appalled by the decision to get the guaranteed payday. The odds are good, possibly great, that Singleton just gave a lot of money away.

Let's review Singleton's credentials and see if history can help us pick a side. Singleton is:

  • A first baseman
  • Ranked #82 in Baseball America's 2014 Top-100 list
  • a player with Triple-A experience

This means that if we're going to dig through BA's top-100 list for historical comps, we should stay away from teenagers in the low-minors and focus on first basemen about to break into the majors. How many of them would have been worth the equivalent of $10 million over five years? From 1990 through 2008:

Worth it (35)

Paul Sorrento
Eric Karros
Mo Vaughn
Rico Brogna
Tino Martinez
Frank Thomas
Reggie Jefferson
John Olerud
Jeff Conine
Ryan Klesko
Cliff Floyd
J.T. Snow
Kevin Young
Dmitri Young
Tony Clark
Derrek Lee
Brad Fullmer
Richie Sexson
Paul Konerko
Todd Helton
Sean Casey
Carlos Pena
Nick Johnson
Jack Cust
Adrian Gonzalez
Xavier Nady
Justin Morneau
Prince Fielder
Lyle Overbay
Travis Hafner
James Loney
Adam LaRoche
Kendrys Morales
Conor Jackson
Joey Votto

Questionable (7)

David Segui
Bob Hamelin
Steve Cox
Travis Lee
Hee-Seop Choi
Casey Kotchman
Daric Barton

Nope (10)

Dave Staton
Dave McCarty
J.R. Phillips
Ron Wright
Calvin Pickering
Eric Munson
Jason Hart
Brad Nelson
Michael Aubrey
Justin Huber
Steve Pearce

If you're mathematically inclined, you might note that "35" is a larger number than both "7" and "17." It's even larger than both of them put together. More than twice as large, even. That's because first-base prospects who hit close to the majors are mostly known quantities. There's almost no way they'll completely flame out.

You might wonder what the "questionable" pile is all about. Those are the first basemen who were probably worth the equivalent of $10 million in 2014 bucks, at least from a raw WAR/$ perspective. It doesn't take much to be worth that much, and those seven all had a good season or two that might have been valuable enough to justify a contract like Singleton's. I'll leave that to you.

The risk is that Singleton is one of the terrible 10 at the bottom. Forgetting that Pearce is in the middle of a surprising renaissance as a solid bench option, those 10 players didn't do anything close to major-league quality work. There were concerns for all of them, whether contact issues (Phillips) or body type (Pickering), but they were all supposed to do something more than they did. Singleton has a similar concern, having been suspended twice for marijuana and labeling himself as someone suffering from drug addiction. That's not a small concern.

Still, it wasn't something preventing the Astros from making the offer. And if those teams took a Singleton-type risk on those players? Well, that would have cost them about two seasons of a left-handed setup man over five years. That's it.

Look at the 35 players above that, though. All Singleton needs to be is Xavier Nady to give the Astros a good deal. Brad Fullmer or Rico Brogna. Even if he's a Casey Kotchman-type, the Astros will come close to breaking even.

I get the risk aversion. If someone came to me with $100,000 in exchange for any money I make on a novel, non-fiction book, or screenplay for the next 15 years, I'd jump at it. Because when I'm not writing this nonsense, I'm actively avoiding writing anything else. There's a chance, though, that while cashing sweet, sweet unemployment checks that I actually write something that makes money by accident. Oh, that would be frustrating.

Right now, though, I'd buy a Playstation 4 with that money. And plumbing that worked. It would be awesome.

Now extrapolate that out to what Singleton's worst-case scenario would be. He'll still be a millionaire several times over. Even if he's Bob Hamelin, he'll be extraordinarily rich. That's a heckuva worst-case scenario, at least financially.

But he almost certainly saved the Astros a ton of money. We're probably on the other side of the giggling-at-the-Astros hill. In a couple years, you'll forget what it was like to giggle at them and the decisions they made. You won't find a reason here. The odds are overwhelmingly on their side. They probably just made an excellent investment that will help them build a better team for the next decade.