Jon Singleton's new contract with the Houston Astros occupies a complicated space in the discussion about money and professional baseball. It raises the question of what constitutes a good contract all across the league, as more and more players bargain away years of arbitration and/or free agency for guaranteed money right now.

First things first. Assuming good financial planning and sound budgeting, Singleton should be set for life, even if he blows out his back two weeks from now and can never set foot on a professional baseball field again. The Astros have guaranteed Singleton $10 million over the next five seasons, with club options and bonuses that could bring the total payout to $35 million. The contract buys out Singleton's pre-arbitration years (for which he otherwise would have been paid the league minimum) as well as his first arbitration year, and it gives the team options to buy out the rest of his arbitration years, as well as his first season of free agency.

The deal is especially good for Singleton given that he's a risky prospect, at least as "name" minor leaguers go. Singleton came into the 2014 season rated 82nd overall by Baseball America, down from 27th overall entering 2013, due to an abysmal season both on the field (.687 OPS over 294 PA, despite hitting in the offense-friendly PCL) and off. (He began the season serving a 50-game suspension for violating the minor league drug agreement's prohibition on marijuana use, and then clearly suffered ill after-effects from quitting the drug cold turkey.) Singleton seems to have his head back in the game this season, but he still has more plate appearances as a bad player in the PCL than as a good one. He also has a fairly one-dimensional profile to begin with, relying on his power translating to the big leagues if he's going to be more than a replacement-level asset.

The Astros rushed Singleton onto the 40-man roster last October, officially putting him under the aegis of the MLB drug testing program, which does not suspend for positive marijuana tests. (Similarly, Jeremy Jeffress was added to Milwaukee's 40-man roster after his second failed drug test, reportedly for marijuana.) Given the substantial risk Singleton entails, $10 million guaranteed, along with the chance to potentially triple that, is a deal he should jump into with both feet, eyes wide open, with dollar signs in them.

His promotion to the big leagues at the same moment the contract is signed makes for some bad optics, however, for a team that was heavily criticized earlier this spring for keeping George Springer in the minors in early April, seemingly because he wouldn't sign away his arbitration years and first season of free agency. The Astros have been feeling increased heat around the industry for the way they deal with players and agents. It's telling that Bud Norris felt comfortable taking shots at a front office that might have been near the front of the line to sign him in free agency, given how well he's performed at Minute Maid Park in his career. (Then again, it could only be telling that Bud Norris doesn't know when to stop talking.)

This is not the first time a club seemed to be tying a team-friendly deal to a prospect getting called up, implying that failure to sign might mean more time on the bus in Triple-A. That would be a clear gaming of the arbitration system -- as is keeping a player down until mid-June in order to clear the "Super Two" cutoff point -- and not something that fans should applaud their teams for doing. But while the Super Two stuff has been going on for a while, Houston could be the first team to suggest to a prospect on the cusp of the majors that if he doesn't agree to a certain type of contract, he'll be staying in the minors a little bit longer. (Pittsburgh seems to be in a similiar position with Gregory Polanco, although the Pirates have denied stalling promotions as a contract tactic.)

Generally speaking, players should take these cost-certainty deals, because a lot them won't live up to their fans' insane expectations. Starlin Castro and Anthony Rizzo were right to sign with the Cubs through 2020, for example, because while the floor could still fall out from under either one of them, neither is likely to ever be much more than what he is right now -- respectively, a defensively flawed shortstop who only hits for average and a modestly powerful first baseman with a serious platoon-split problems. These contracts often are disasters for the teams involved, though, which is one more reason why fans should be leery of deals that are tied, implicitly or explicitly, to promotion.

All told, though, it's a good sign that the Astros are doing this now. For whatever reason, Houston is kicking its roster improvements into high gear. We've been saying for years now that, sooner or later, the Astros were going to turn things around. Over the past couple months, it's finally looking like sooner rather than later.