Let’s get this out of the way – the Red Sox still have not begun any sort of talks with Jason Bay and his agent, Joe Urbon, regarding any sort of contract extension.
Yet.
The Red Sox have made a living out of signing players to extensions before feeling the discomfort that comes with free agency. Josh Beckett. David Ortiz. Dustin Pedroia. Kevin Youkilis. It has become one of this regime’s calling cards and most successful tactics.
But when it comes to Bay, time is ticking. One season stands between the left fielder and the open market, which, in his case, is looking better and better all the time (even in this economy).
Bay will be making $7.5 million this season, finishing off the final year of the four-year, $18.25 million extension he signed with Pittsburgh in 2005. Next year at this time, that annual number could very easily double, with the Red Sox facing the daunting task of finding another middle-of-the-order bat/left fielder.
“I would say 50-50,” said Bay from his home in the Northwest when analyzing the prospects of ever reaching free agency. “But I love Boston.”
There is little doubt that Bay’s almost three-month stay with the Red Sox last season left an impression. He liked the atmosphere (“It’s like chugging coffee almost all the time”), enjoyed his teammates, manager and everything else about the team to which he will be reintroduced when he heads to Fort Myers on Feb. 15.
Yet there is a reality that neither Bay nor the Red Sox are ignoring – as it currently stands, if the 30-year-old files for free agency next offseason, he will most likely join Oakland’s Matt Holliday and the Angels’ Vladimir Guerrero as the most sought-after bats in the market.
Bay admits he has been glued to the computer screen this winter following the changes in the baseball landscape.

“My wife said I’ve reached the end of the internet,” he conceded.

He just might be running into his name appreciably more if that free-agent scenario plays out.
“(Boston) becomes more favorable because I was able to take the unknown out of it,” Bay explained. “I got almost a three-month taste.”
And as much of a solid impression as the Red Sox left on Bay, the player smothered the team with an equally heavy dose of good vibes thanks to his second half production.
Those unfamiliar with Bay before he headed over to the American League in the memorable Manny Ramirez deal at the trade deadline came away with an appreciation for more than just the outfielder’s bat. He surprised many with his work in left field, and a surprisingly effective ability to run the bases.
As for his performance at the plate, Bay led all left fielders in the second half in OPS (on base percentage plus slugging percentage; .897) and home runs (9).
And he did this while living in a shadow – that of Ramirez – that he now admits was a bit more consuming than he previously let on.
“It’s easy for people to say not to try and replace (Ramirez),” Bay said. “But it’s a lot tougher to buy into it.”
And immediately answering doubts – first in August (.315) and then in the American League Division Series (.412) – while fending off Jumbotron images of Ramirez’s West Coast exploits provided a powerful elixir as well.
“In hindsight, in all honesty, that definitely helped,” said Bay of the good starts. “At the time I was downplaying it because I didn’t want to put any undue pressure on myself, but it was human nature (to feel the pressure). Getting off to those starts was a huge part of my success.
“I was well-received by the fans right away and that really helped ease my transition. When you have to go into a situation where there are a lot of unknowns those little things go a lot further than people understand.”
Bay’s success could also be attributed to his ability to adapt. He references how surprised he was regarding the constant wave of power arms coming out of every opponent’s bullpen. The outfielder also flipped the script a bit when it came to his approach at the plate, swinging earlier in the count in order to cut down the insecurity.
His pitches per plate appearance dropped to 3.90 from the 4.14 clip he was totaling with Pittsburgh in the season’s first half.
“It was a big adjustment,” Bay said. “Familiarity (with the pitchers) was the biggest adjustment. I would go over things with (hitting coach Dave Magadan), but he can’t do everything. I would simply wait for the first good ball I saw and swung at it.”
So with Bay passing virtually every test thrown at him in what can often be the intimidating world of baseball in Boston, his value continues to increase.  Finding meat-of-the-order hitters simply isn’t easy, especially when it comes to delving into the competitive free-agent market.
(Oh, and by the way, when it comes to Bay’s preference in regards to what spot he likes in the batting order, he notes, “I’m comfortable wherever they put me. There isn’t a spot I don’t like.” Just something to think about when looking for cleanup-hitting options if Kevin Youkilis is called upon to hit elsewhere.)
The Red Sox may very well choose to once again rely on a farm system that has rarely let them down, eyeing the emergence of outfielder Josh Reddick. The almost-22-year-old’s power continues to trend upward, having hit five home runs in just 23 Arizona Fall League games this offseaon after totaling 23 between Single- and Double-A last season.
Or the organization could lock into another option via trade, or stop-gap, following next season, choosing not to allocate the money or years that Bay is most likely going to command.
But, no matter what the plan, the memory of how uncomfortable free agency can be for both the teams and the players should be rekindled when looking at the case of Bay.  Signed or not, this guy could be the next big deal for the Red Sox.