If the Red Sox sign Ellsbury long-term would they regret it like they did the Crawford contract? With the Red Sox facing the Dodgers as the one-year anniversary of the Nick Punto trade looms it's time to think about what that deal meant to Boston. The Red Sox were able to shed significant salary and long-term deals and that allowed them flexibility that simply didn't exist in Ben Cherington's first off-season as the general manager. That's how they ended up with productive short-term players like Mike Napoli Shane Victorino Stephen Drew and Koji Uehara and also how they were able to add Jake Peavy before this year's trade deadline when a need opened up in the rotation. It's a significant reason if not the reason that they're in first place in the East and leading the American League in wins. It's also time to think about what the deal has yet to the mean for the Sox and the building of future squads. More specifically if failures in the past mean the Red Sox should be avoiding long-term deals in the future such as with impending free agent outfielder and all-star Jacoby Ellsbury. Even the idea of a long-term and expensive Ellsbury contract with the Red Sox has some fans reeling as they simply can't handle risking another Carl Crawford. There are many many reasons though why an Ellsbury deal wouldn't have to be that way. Just because spending money didn't work with Adrian Gonzalez and Crawford -- and remember it nearly worked in 2011 -- doesn't mean it's always a poor strategy. It's about what the money is spent on and leaving yourself room to work once said spending is done. The problem in 2011 wasn't so much that Carl Crawford was hurt though it certainly played a part: it was that the Red Sox didn't have the financial flexibility to do something about it or to patch holes elsewhere like in a rotation that couldn't even afford the duct tape needed to patch it back together.