beckdawg
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For me I am not so sure. They've passed to date on doing so. They'll almost have to if they are going the FA route for pitching and their young stars approaching "real money" status rapidly.
The thing to remember is the way they've built their pitching in their farm system. They have literally like a dozen guys who probably end up some where between a #3 and a #5 starter. In other words, in the next 2-3 years it's an utter lock that you're going to be able to fill 3 of the 5 starters internally so you're really only talking about potentially spending money at the top of the rotation. If for example you say a playoff caliber team spends like $30 mil on a #1, $25 mil on a #2, $15 mil on a #3 and like $10 mil on a 4 and 5 that's $90 mil. On the other hand, if the cubs can continually pump out 3-5 starters you can pretty easily spend $25-30 mil on FA starters at the top of the rotation and continually trim down the older guys from #1's to #3's and so on by paying them more up front and making their value as they age better.
When you think about it in that manner from a development standpoint it is kind of intelligent. You're not risking all that teams do trying to find the next big pitching prospect. And while sure you may miss out on home grown Kershaw's and Sale's, you aren't dealing with all the busts that lead to those successes. And in terms of where in the draft the cubs are finding these guys it's not early. Obviously you're going to mix in guys like Lange/Little from time to time but Michael Rucker was an 11th round pick and he's almost certainly going to pitch in the majors. Hatch was a third round pick...etc.
The issue they have in my eyes is all of that hitting talent left a giant hole in their farm system from a hitting perspective. It's really not very pleasant above South Bend. You can probably count on one hand the number of guys who are realistically guys who stay at the MLB level their entire career. So, they really need to be able to ride this wave for 3-4 more years without dipping too much into hitting prospects in trades.