Tony Massarotti’s latest article at the Boston Globe deals with the Sox payroll — both short-term and long-term versions of it. It’s something we’ve been exploring a bit here at Fire Brand, and Mazz does a great job tying it all together.

I was planning on bringing up this subject in later articles, but I might as well now, given the money quote here:

The biggest question Epstein may be faced with this offseason will result if he fails to sign either Bay or Holliday, leaving the Sox with a fistful of money and no marquee free agents to spend it on.

When that happened last year, Epstein signed a handful of pitchers to one-year contracts and rolled the dice that the Sox could pitch their way to a world title. And though that plan ultimately fell a few steps short, the Sox essentially are right back where they started.

With a roll of cash in their pockets, faced with the decision of spending it now or spending even more later.

As I’ve alluded to, this free agent class is horrible when it comes to making significant investments on the free agent market. There is no clear “break the bank” player. Bay understands he isn’t one, but is gunning for years, reportedly. Holliday is pretending he’s one. So what is Theo to do? Break the bank now or later?

The Sox attempted to do this last year with the signing of Mark Teixeira, but Theo’s conservatism cost the BoSox big time — and you can bet he realizes this.

So, to reiterate: Do we spend now or later? You decide, but let me just point out potential 2011 free agents:

Carlos Pena (who may cement himself as a major free agent target — he’s close), Julio Lugo (had to, just for kicks), Derek Jeter (hey, he wants to play for Boston), Adam Dunn, Jayson Werth, Josh Beckett (so we need to try and resign him), Roy Halladay, Huston Street and of course… Joe Mauer.

So tell us. Spend now or later?