My concern is not so much with the Ellsbury decision in isolation, but with what appears to be an organizational decision not to seriously compete to re-sign our best players when they hit FA in their late 20s/early 30s. I fear the team is moving towards a de facto refusal to sign FA (including especially our own) in the absence of a significant hometown discount.
Ellsbury is the most obvious example, and the Lester contract negotiations seem to fit the pattern too. Unless I am mistaken, we havent been significant players for the very the top level of FA for years. Pedroia and Buchholz are signed on a signficant hometown discounts. Papi is a partial exception I suppose, but the last 2 have been short deals, and before that, if I have it right, Ortiz left money on the table.
As others have pointed out, if you are not prepared to "overpay" periodically for the best players in the FA market, then you have effectively shut yourself out of that market.
The end result of this threatens to be a team built on homegrown 20 somethings before they hit FA, vets who are prepared to leave significant money on the table and B/C level FAs to fill the gaps. Yes, it is a strategy which won a WS for us in 2013, and it might do so again. It is an approach that certainly has its benefits for the owners. But as a fan, it has equally obvious drawbacks, including the shittiness of watching Ellsbury play CF (or Lester pitching) for the Yankees, and the sinking feeling that one ought not to get too attached to the likes of Xander Bogaerts given that if this approach holds he will be playing SS for the Yankees (or some other team willing to "over pay" him) in 6-7 years.