By Spike Eskin

PHILADELPHIA (CBS) – Remember the day the Phillies announced Ryan Howard’s contract extension? I do. Though there were some who were cautious (even negative) that the deal was risky, expensive, and unnecessarily early, but most of us were celebrating.

Sure, they didn’t need to do it just yet. But the Phillies are made of money, right? And they’re just going to keep on winning, no matter what. Right?

It’s three years later, and it doesn’t seem like either of those are true anymore. We were high on winning, and maybe lost a little bit of perspective. Perhaps the Phillies did as well.

Jonah Keri of Grantland rated the 15 worst contracts in all of baseball, and Howard’s came in third, behind Alex Rodriguez and Carl Crawford.

Signing a player to a gigantic long-term extension a year or more before his existing deal ends has become a relatively common practice, with Troy Tulowitzki, Evan Longoria, and others working out variants of that arrangement. But when Ryan Howard put pen to paper on a five-year, $125 million extension back on April 26, 2010, with nearly two full seasons left on an existing three-year pact, this was something new. It was, according to multiple baseball analysts, a catastrophe. Or as Keith Law put it at the time:

This is one of the worst extensions of its kind — it’s an overpay in both years and dollars. Howard is one of the last guys in the middle of the lineup I’d give that kind of money, too. He’s 30, has a bad body, is not a good defender, and has struggled to make contact versus lefties — he’s gone backwards in that area over the past couple of years. If you were locking him up through age 31, it’s not so bad. How happy are you if you’re Albert Pujols? If Howard is worth $25 million, Pujols is worth $50 million a year.

Other than that Pujols bit, that’s pretty damn spot-on. Howard did get in better shape not long after signing the extension. He also suffered a brutal Achilles injury at the end of the Phillies’ 2011 playoff run, which combined with a late-2012 broken toe and other ailments cost Howard 91 games and limited his season numbers to a hideous .219/.295/.423. Year 2 of the megacontract is in doubt too, with Phillies GM Ruben Amaro Jr. saying he doesn’t expect Howard to fully heal from his torn Achilles until some point during the season. This was the worst-case scenario, to be sure. Still, the Howard contract, which has four years and $105 million left on it (counting a $10 million 2017 buyout), was yet another in a long line of deals signed more on the basis of past performance than realistic future expectations. It was also a case of overrating power hitting above all other skills. As much as we’ve learned about the value of defense, baserunning — of being a well-rounded player, really — it’s the Ryan Howards of the league who still rake in the biggest bucks. Unfortunately, this particular example isn’t as good as the others, and is damaged goods. The Phillies wanted a long-term commitment. They’ve got one now, whether they still want it or not.

To make matters worse, even though closer Jonathan Papelbon didn’t make the list, he did get an honorable (dishonorable?) mention.

To see the full list of fifteen, visit Grantland.

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