Before I start writing, I would like to note that this is pure speculation on my part.
Jason Bay is set to be a free agent after the 2009 season, and has yet to talk extension with the Boston Red Sox.
Could this be on purpose?
While Bay has without a doubt provided a great bat in the middle of the Red Sox lineup, there are still better options out there, and Boston may be interested in pursuing them.
Matt Holliday, also a free agent next winter, could very well be one of those options.
Matt Holliday's talent is certainly not in question. In five full seasons, here is Holliday's track record:
2004: .290 AVG, 14 HR, 57 RBI
2005: .307 AVG, 19 HR, 87 RBI
2006: .326 AVG, 34 HR, 114 RBI
2007: .340 AVG, 36 HR, 137 RBI
2008: .321 AVG, 25 HR, 88 RBI
While Holliday's talent has been proven over the past four years, what sort of money he, or his agent, rather, would command on the free agent market is still a question.
Holliday is a Scott Boras client who will be in a very weak free agent crop. With this being the case, Holliday is likely to get a king's ransom on the market.
However, the Red Sox may not be opposed to doling out the money. Barring a surprise move, the Yankees don't look like they'll be in the Holliday sweepstakes.
While there is nothing wrong with Jason Bay, he could possibly be a bridge between Manny Ramirez and a possible Matt Holliday acquisition.