Zell's Pinstripe Blog

According to the Daily News, sources indicate that there is a split between Theo ‘Whiz Kid’ Epstein and owner John Henry about the potential acquisition of Roy Halladay. Apparently Epstein doesn’t want to part with Clay Buchholz, Josh Bard and Casey Kelly while John Henry appears to be the main effort behind the possible completion of such deal. Epstein would prefer to use those players in a possible deal for Adrian Gonzalez or former Red Sox farmhand Hanley Ramirez.

John Henry prefers to load up on star power as opposed to cultivating homegrown players, which really shouldn’t come as a surprise as he used to be a limited partner with George Steinbrenner. Henry is also tired of letting marquee players go the Yankees instead of his Red Sox (See: A-Rod, Contreras, and Teixeira). If I was in Henry’s place, I would feel slightly the same watching the parade of marquee players agreeing to wear pinstripes.

If the Yankees acquire Roy Halladay, this deal could hypothetically provide bigger dividends for the Yankees not only in the short term, but possibly the long term future. In this case, I’m coining ‘long term future’ as 5-10 years from this point on as long as John Henry is the owner of the Red Sox. In reality, Henry can only hold on so long while the Yankees sign or otherwise acquire personnel that Boston desires. If Henry acquiesces to Epstein’s long term plan of developing homegrown players (and doesn’t acquire Halladay), the question that comes to my mind is how many more players will the Yankees acquire that Boston desires before Henry blows up Epstein’s plan?

If Henry does blow of Epstein’s plan and the Red Sox acquire players like the Yankees did earlier in the 2000’s, its possible that a few years down the road, the Red Sox could experience the same heartache the Yankees felt with repeated early playoff exits between 2002-2008 (sans 2003).

Assuming that there will be a split for the short term future, it might actually help the Yankees in the acquisition of Roy Halladay. If the Red Sox hierarchy can’t come up with a proper package that both makes Henry and Epstein happy while meeting Toronto’s demand, it could drive the Blue Jays to make a deal with the Yankees. We already know at this point Halladay would waive his no trade clause to come to the Bronx, so that is one hurdle taken care of. However, it is hard to imagine that the Red Sox, regardless of the issues between Henry and Epstein, would not be involved in Halladay talks. Halladay wearing pinstripes would tip scales fully in the Yankees favor — not that they aren’t already.