In the final two months of 2008, Jason Bay had to answer question after question. Though he made a transition to Boston with what seemed like remarkable ease, he nevertheless was viewed as a great unknown at every step of his first three months with the Red Sox. 

Could he handle the scrutiny of playing in Boston after a career spent almost entirely on losing squads in Pittsburgh? Could he succeed in the face of the inevitable comparisons to Manny Ramirez, the man whom he replaced in left field for the Sox? Would he wilt amidst the pressure of the postseason?

Now, as he prepares for his second playoff run, Bay is no longer treated with suspicion. The 31-year-old has responded to every challenge that has faced him by delivering consistent production to the Boston lineup. He has shown that the skills he demonstrated in Pittsburgh were not a byproduct of playing for an uncompetitive team, but rather a reflection of his abilities.

Bay understands why the questions were asked about him. He also understands that he will no longer have to face that particular line of inquiry based on his 14 months with the Red Sox.

“You come over from the market I was in and a playoff situation, from where I was and to come to this one, it was like, 'Boom.' Everybody is going to have their questions, everybody is going to have their doubts,” said Bay. “It was not like I never wanted the chance [to play for a contender], I just never got the chance.

“Obviously it went fairly well for me,” Bay continued. “I was never trying to prove anything to anybody, but at the same time, I think the way things went for me, now that that is behind me, it makes going forward a lot easier.”

Indeed, Bay suggests that his time in Boston has been, in many ways, even more enjoyable this year than it was a year ago. In 2008, he endured a “whirlwind” as he tried to relocate in the middle of the season and make himself at home in a new city and clubhouse.

This year, he has felt a part of the Sox since he first reported to spring training. As such, he has been able to take full advantage of a culture in which he has been able to ignore issues of personal success and instead focus solely on winning.

Last September, Bay marveled that he felt energized to be in a pennant race for the first time, in contrast to the years spent dragging toward the finish line in September. One year later, with just days separating him from the postseason, the three-time All-Star suggests that is still in many ways the case.

“I think the novelty of [being in Boston] has worn off, but the atmosphere and what comes with it has not. Nor will it,” said Bay. “Last year, a lot of things were, not overwhelming, but new at times. You’re going left and right and trying to figure out and then two months go fast for me. And this year the ride has been a little slower. It’s not over yet, don’t get me wrong, but I’ve had more of a chance to really, I guess, kind of enjoy it.”

Certainly, his performance has left him wanting for little. He has set career highs in homers (36) and RBI (116) while producing an elite .923 OPS. In so doing, he has shown that he is capable of thriving regardless of the setting or stage, just as he did in hitting .341 with a .471 OBP and .634 slugging mark last year in the playoffs.

That is not to say that his tenure with the Sox has been without challenges, or the occasional new line of inquiry. When he finally endured his first struggles with the Red Sox over a two-month stretch this summer, it was fair to wonder whether he could handle adversity in such a public setting, or whether contract negotiations with the Sox might get in the way of his play.

Even Bay at times wondered about some of those matters. But life on a contending team allowed the outfielder to look beyond such issues.

“Whoever is going good or bad, if you are winning games your slump does not get magnified. It’s kind of a side note: ‘still struggling.’ Winning, that’s the ultimate goal,” said Bay. “For a lot of reasons it was easier [to deal with a slump in Boston] but at the same time, obviously you’re in a bigger market, more people are talking about it, it’s a contract year, so you’ve got people and that angle on it, what it is and all these people are trying to figure out.

“I treated it like I always did and it never seemed any different, other than some external factors being here and dealing with it. I kind of felt like I struggled before and I had something to draw upon in dealing with it.”

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Bay’s performance sagged for roughly five weeks this season, as he hit .165 with a .581 OPS, one homer and five runs batted in during a 31-game stretch that ran from late June through the end of July. Because that rut happened to coincide with a period when Bay was engaged in negotiations about a possible extension with the Sox and then the time immediately after those talks were tabled, it was easy to connect Bay’s contractual status with his dip in performance.

But Bay insists that it would be a mistake to view the slump and the course of his talks as anything but a coincidence.

“To be honest with you, when things were going well I didn’t think I was going to break the bank and when things got real bad I wasn’t thinking I’ve ruined my season by any means,” Bay said. “I am pretty good at taking things for what it is every day and I never, even at this point, I am not thinking with every RBI I get I am adding an extra X amount ... I don’t buy into that stuff.”

Bay has never carried himself as a player on a contract drive in Boston. He has maintained a remarkably steady demeanor throughout the year, regardless of his or his club’s performance.

Because of that, and because Bay has emerged from that slump with a monster final two months, having hit .292 with a .390 OBP, .646 slugging mark and an AL-leading 16 homers since Aug. 5, the outfielder has positioned himself for a substantial haul in free agency.

Multiple industry sources expect that bidding for Bay — who is making $7.5 million this year in the final season of a four-year, $18.25 million deal he signed while with the Pirates — will reach at least four years at $14 million-15 million per year this offseason should the outfielder seek to maximize his worth on the open market. Indeed, some have suggested that he could exceed those estimates, both in years and dollars. Certainly, it could help the slugger’s cause that the number of interested teams is expected to be significant.

Simply looking at the teams that will have money coming off the books and a potential outfield position need, one could envision the Angels (especially if Bobby Abreu leaves), Cardinals (if Matt Holliday departs), Giants, Mariners, Mets and Yankees, among others, jumping into the fray if Bay does not re-sign with the Red Sox.

While life on that wining-and-dining free agency circuit may soon beckon, however, it seems of little concern right now to Bay. Just as he has issued a powerful rebuttal to all of the other questions about his performance in Boston, so, too, does he wave away the notion that his focus is on anything but what his team has accomplished thus far in 2009 and what it may yet achieve in the weeks to come.

“After being in the situation I was in Pittsburgh, I think there is a lot more to be said for being part of a whole, the team winning games and how you fit into that,” Bay said. “Granted, my numbers suggest that I am part of that … I hope that when things are said and done, my numbers will be there so people can just say, ‘Hey, you did your part.’ ”

It would be difficult to suggest otherwise, since the questions about what Bay might deliver for Boston in any given situation have long since been dismissed. In their wake is the sense that in the 2009 playoffs, just as was the case in the regular season, the Sox will need Bay to be exactly what he has been ever since joining them last summer.