The Philadelphia Phillies on Monday signed star first baseman Ryan Howard to a five-year, $125-million contract extension. There were many different reactions to the news on the Interwebs, with most saber-friendly writers coming out strongly critical of the Phillies.

Howard, of course, is an exceptional hitter. He has posted a career line of .279/.373/.582 while averaging 49 home runs and 142 RBIs over 162 games during his seven seasons in the majors. While he gets overrated a bit because of the lofty RBI totals, in some part the function of having good teammates setting the table in front of him, and struggles against lefties, he is a legit stud hitter. Plus, he is a Philadelphia fan favorite, the clear face of the organization and one of the most marketable players in the sport.

But the timing and risk associated the move are hard to ignore. Why not simply wait to see how Howard ages over the length of his current contract? Indeed, there was simply no real incentive or rush for them to make this type of move right now, especially when factoring in the basic concept of positional scarcity (it is not all that difficult to find offensive production from the first base spot) and the opportunity cost of where else that money could have been invested.

In the short term, Howard will likely remain a productive force in the middle of the Philadelphia lineup, but, even so, has only been worth greater than $25-million one time during his career according to FanGraphs.com. Down the road, as a result, this deal will likely end up looking just terrible. First baseman, especially ones with an old man skill set like Howard, generally do not age well. The lefty slugger, having broken into the majors at 27, is already pushing 30. If he is struggling to live up to his current salary now even with improvements in conditioning and on defense, imagine how difficult it will be in his early-to-mid-30s when he will be one of the highest-paid players in baseball history.

So, while many fans are happy about the announcement now, keep in mind that most Boston Red Sox fans were happy when David Ortiz was extended for $52-million over four years back in April of 2006. How do Red Sox fans think about that move now? Even in that example, though, Ortiz put up two excellent campaigns in 2006 and 2007 and was somewhat decent in 2008. However, there was considerably less risk on Boston’s end than in the current example with Howard, who truly could end up as the next Mo Vaughn. Hence the gif image above.

See also: Howard gets new contract thanks to agent Jared Fogle.