At some point late last night after news of Philadelphia lavishing a 5 year, $125 million contract extension on slugger Ryan Howard — who still had two years to go on his existing pact — one keen observer mused the deal “will take him past his 37th birthday. By contrast, David Ortiz won’t be 35 ’til November.”  “Howard doesn’t even have to fall off a cliff in the next five years for this deal to be bad. It’s bad on day one,” pronounced Hardball Talk’s Craig Calcaterra (“while he’s better than he was on defense, he’s still bad and, before this contract was signed, seems like a guy who was on the DH-express”), and while Calcaterra is quick to cite Howard’s solid citizenry, that’s not nearly enough to impress FanGraph’s Matt Carruth who confesses, “when the news first broke and the details started to emerge, I was tempted to fill this entire article with just me laughing.”

Projecting Howard™s performance from 2012-7 is incredibly difficult. We™re not only looking very far into the future, but we™re doing so with a hitting profile that historically ages awfully. Richie Sexson, Cecil Fielder, Mo Vaugn, David Ortiz, Tony Clark and others are among Ryan Howard™s most comparable hitters according to Baseball-Reference. All of them dropped off harshly in their early 30s. About the only success story in Howard™s top ten comparables in Willie McCovey.

Even if you think baseball™s salary per win goes up to $4.25 million this coming offseason and rises at a 5% clip every winter through 2017, Howard will need to produce an average of 4.75 wins from 2012 through 2017 just in order to justify his salary. If you factor in that Howard gets (even more) long-term security from this deal, then that average production levels goes up to 5.3 wins.

In other words, Howard will need six seasons that were better than his 2009 season, except over his 32-37 years. I™m not sure I would lay even money on him achieving even half of that. This contract is both incredibly risky and unnecessary since Howard was already signed through 2011. Say hello to baseball™s newest worst contract.

The St. Louis Post-Dispatch’s Bernie Miklasz concurs with many of the negative opinions about the Howard extension, arguing it “seems to be an example of an overanxious front office working against itself.” Of course, Milasz is well aware that such a windfall for Howard will make things that much harder for the Cards to retain Albert Pujols (or for the Brewers to keep Prince Fielder).  And therein lies the genius of Ruben Amaro —he’s laid the groundwork for one, possibly two otherworldly sluggers to leave the National League and sign with the Yankees, Boston or Anaheim in the near future.