Come To Think Of It: Will Red Sox Have Happy Hollidays Or Halladays?

Bob Warja@@bobwarjaSenior Writer INovember 26, 2009

BOSTON - AUGUST 26:  The U.S. flag flies at half staff in honor of the late U.S. Sen. Ted Kennedy (D-MA) before the Boston Red Sox take on the Chicago White Sox on August 26, 2009 at Fenway Park in Boston, Massachusetts.  (Photo by Elsa/Getty Images)
Elsa/Getty Images

Matt Holliday...Roy Halladay...this offseason is so damn confusing. But we know one thing - both players are available and at least one will sign a huge deal this off-season. Will one of the teams that bites be the Red Sox?

Look, with apologies to Jason Bay and John Lackey, Matt Holliday is the best free agent on the market. Lackey is good, to be sure, but he's the best starting pitcher in a weak market.

Meanwhile, the only question surrounding Holliday is which player will show up for the team that signs him? The one in Oakland who seemed to further the idea that Matt was simply a product of the thin air in Denver, or the guy in St. Louis that destroyed NL pitching?

We do know that Holliday is better defensively than Bay, and we also recognize that he is represented by uber agent Scott Boras, so he will command a bigger contract for his services.

Still, the Red Sox, among others, are said to be interested in Holliday. Or is that Halladay? I told you this is confusing.

There are almost equal reports that the Sox are aggressively pursuing Doc from the Blue Jays, though I would think the key to any deal would be a contract extension.

If Doc was only a one year rental, the Jays know they wouldn't get as much for him. But if they allow a window for a team like the Sox to negotiate an extension with the star pitcher, well, that's a different story my friend.

For it's clear the Sox need starting pitching. Tim Wakefield is 44 years old. Dice K is coming off of injury and poor performance. Clay Buchholz is unproven.

Of course, Buchholz is likely to go as part of any package used to acquire Halladay. But in the AL East, you simply can't afford to stand pat, you have to take chances.

What would it take to sign Holliday? Try seven years and $126 million dollars perhaps. I don't see the Sox going that high.They could just as easily trade for Doc and sign Bay.

And what would it take to extend Halladay? Likely $20 million dollars per year but perhaps over a shorter time period. Let's say, for the sake of argument, four years, $80 million dollars. That may be more appealing to Theo Epstein.

I don't think any of this is going to materialize quickly. Still, it is the holidays. Or do I mean the Halladays? I told you this stuff was confusing, come to think of it.