Should the Phillies Wait to Extend Cole Hamels or Do It Now?

Cole Hamels is a World Series MVP, a world-class pitcher, left-handed and just 28 years old.  He's got that SoCal cool about him, a slightly high-pitched and nerdy sounding voice and a smokin' wife who once stripped for peanut butter during a challenge on Survivor.

He's also going to be very, very, very rich very soon.

Many experts believe that the six year, $127.5 million dollar contract extension Matt Cain signed at the beginning of April set the market for Hamels' extension.  I personally believe he's worth even more, and that he could easily garner $150 million or more on the open market this winter.

And so the Phillies have a dilemma on their hands: Should they push to re-sign Cole Hamels as soon as possible, or should they wait until after the season to address the issue?

The Case for Signing King Cole Now

The case for signing Hamels as soon as possible is pretty simple: He is really good, he is still young, he's come up through the Phillies' system, his teammates and the fans want him to stay.

There aren't many pitchers like Cole Hamels in baseball—lefties with killer change-ups and proven playoff credentials.  With the Phillies core players getting older, and with Halladay and Lee both due to decline eventually, re-signing Cole Hamels is a chance for the Phillies to keep their hold on a player they can count on for the next seven or so years.

If the Phillies front office believes that this team's window of high quality play from players such as Halladay, Lee, Ryan Howard, Chase Utley and Jimmy Rollins will remain open for the next couple of years, then they ought to sign Cole Hamels;  having a pitcher of his caliber gives the team its best chance to win another championship or two while the window of dominance is still open.

Plus, Hamels is killing it this season.  The longer the Phillies wait to re-sign him, and the more dominant starts Cole has, the higher his price gets.  By signing him sooner rather than later, the Phillies will probably save themselves some money.

The Case Against Signing Husky Hamels* Now

*First of all, I am officially taking all credit if this nickname catches on.

But in case you haven't noticed, the Phillies are old.  I mean, Polanco is practically moving around with a cane out at third, and I think Jimmy Rollins left his dentures on the field between innings the other day.

Clearly I'm exaggerating a bit, but this is a team that oftentimes lacks a youthful spark.  And as important as it is to keep Cole Hamels around, it may be even more important to think big picture and acquire some young pieces to fill in for some of the players on their way out.  

If the Phillies sign Cole Hamels now, that essentially takes the option of trading him for a potential bounty of young talent off the table.  Sure, Hamels is great, but is it worth keeping one stud pitcher at the expense of three or four players that may range from studs to capable starters?  I don't know, but that's certainly a "would you rather" that the Phillies' office must be thinking about long and hard.

Also, there's the issue of all that green, watermarked paper with dead presidents on it.  Hamels is going to be expensive—like really expensive.  For a team that has hundreds of millions locked up in aging players for years to come (Halladay, Howard, Lee, Papelbon, Rollins, Utley), re-signing Hamels for $150 million might handcuff them from doing any type of rebuilding that would be essential to keep this team competitive into the future.

My Opinion

I don't really know what the Phillies should do.  I am neither as baseball-savvy, as slick or as well-dressed as Ruben Amaro Jr.

I guess it all depends on the team's performance this season.  If the team is really doing well come July, and the early season struggles just seem like a blip on the radar by then, the Phillies may be better off holding onto Cole.  Who knows, maybe Utley gets a knee transplant, Howard comes back strong and J-Roll stops popping every pitch up in the infield?  Maybe the Phils' nucleus really does have three or four more great years and they can find players within their own organization (Dom Brown, Galvis, Cody Overbeck, Trevor May, etc) to take the reins.

On the other hand, if the team doesn't look competitive at all in July, it may be time to pull the trigger on a deal for Hamels.  I love the dude. I remember watching his first career start against the Reds, but I also love winning and smart baseball decisions.  This team needs youth, and to sink $150 million into Hamels when he's surrounded by decaying, expensive stars might not be the recipe for success.  

Another option that I've heard floated is that the Phillies may trade Hamels for some prospects mid-season if they are struggling, then come back and sign him after the year.  Groovy.  That might just be the best of both worlds if the Phillies are still scuffling around the trade deadline, but I wouldn't hold my breath on this situation coming to fruition.

So, what do you think?  Try and sign Cole now or not?