NEW YORK -- The question was posed to David Ortiz: "Do you think you have a better shot at getting a two-year deal heading into this offseason than at this time last offseason?"

It was met with another inquiry.

"I'm going to ask you that question," he said. "What do you think?"

All things considered -- the Red Sox new financial flexibility, the increased need for a middle-of-the-order hitter and another productive season (albeit for 3 1/2 months due to an Achilles tendon injury) -- the answer was "Yes."

"There you go," Ortiz responded, nodding his head. "There you go. I agree with you."

According to the Red Sox' designated hitter, there have already been signs this offseason might be more palatable for the 36-year-old. For example, there has been an engagement from the team's decision-makers, the likes of which didn't surface last year until well into what became an uncomfortable journey toward accepting arbitration.

"I can tell you what I'm thinking. I can't tell you what they're thinking. But right now it seems like things will be different than last year. We'll see," Ortiz said prior to his team's 10-2 loss to the Yankees. "They're interested in bringing me back.

"Last year I didn't hear anything until they tried to offer me arbitration. This year, they already said they're interested in bringing me back. That's why I'm telling you we're not going to go too far on this."

Still, while Ortiz is heading into this offseason with more optimism than after the 2011 campaign, he also is still carrying a good amount of trepidation.

After '11, he was coming off a season in which he finished eighth in the majors in OPS (.953), his best output since 2007. And considering the scarcity of middle-of-the-order bats in Major League Baseball, there was a level of comfort heading into what figured to be Ortiz' first foray into free agency.

But it didn't work out like the DH thought it might when October and November rolled around.

There was a two-year offer from the Red Sox, but only for a total of $18 million. Meanwhile, the rest of the teams awaited his decision regarding the acceptance of arbitration before full diving in. The end result was an agreed-upon one-year, $14.565 million deal that led into the '12 season.

"I wasn't happy with what was going on," said Ortiz of how last offseason unfolded. "I don't think I was the right guy to be involved with what we went through last year with arbitration and this and that. Nobody ever thought a guy like me thought I was going to be part of an arbitration case. The bottom line is that it wasn't on me. It was some people making a decision they thought would benefit them. Last year proved sometimes not all the decisions we make are the right ones. Humans, we normally learn from our mistakes. Hopefully that's the case.

"Nothing will surprise me. You guys already know my desire to come back and play here, but if we walk into the wrong situation that can change because the minute I see things are going the direction they were last year then I'm going to tell myself, 'OK, it seems like I'm not important here, so it's time to move on.'"

So, now what?

Despite his Achilles tendon injury, which limited the slugger to just 379 plate appearances, Ortiz has seemingly positioned himself in a fairly favorable spot with two games left until the next offseason. At the time of his injury, he had the third-best OPS in all of baseball (1.024), while totaling 23 home runs. Even a month after the ailment had sidelined Ortiz, he still led the team in home runs by three, while totaling the third-most RBIs. The Red Sox were also 46-44 with the DH in the lineup, making him the only member of the Opening Day lineup to finish the season with a winning record while on the field.

But there will be the debate regarding the value of the designated hitter, and some concern over his age and injury.

In Ortiz' mind, however, none of that should lead to another uneasy offseason. The Red Sox figure to have a need for the kind of talents he possesses. And there's a reason Ortiz has made it clear remaining in Boston is his first priority.

"The bottom line is things are going to be different this year," Ortiz said. "I'm not planning on going through the things I have been going through the past couple of years in the offseason. Hopefully we don't have to go there anymore."

Still, until the offers are made (none of which have been presented), there is always going to be some discomfort this time a year. It's just that this time around for Ortiz, the anxiety isn't quite as prevalent.

"The bottom line is, what am I asking? A four or five year deal? No. I was asking for two years last year and a year has already went by and they're thinking about signing me already," he explained. "If they sign me for two years it would be easy. We wouldn't have to be talking about contract right now.

"Hopefully everything goes well. This is the part of the season I kind of hate the most, when I have to sit down and start talking about contract situations. I hate the part people -- not all of it, but some of it -- they want to make it sound like it's my problem. I can never sign on my own. It isn't my problem. I can't be part of the ball club if I'm not signed, so it's not on me. I never ask for something I don't think I've earned. I never asked for anything ridiculous that I know I'm not going to get. The contract we've talked the past couple of years was a two-year deal. Hello, people. Anybody can get a two-year deal out of nowhere if they know you're capable of playing and put up numbers. That's the easiest thing to do in today's game, give a two-year deal."

Easy? Yes. A lock? Not quite yet. The lessons of last year still linger.

"I thought I was in a good situation last year," he said. "It's not all about being in a good situation or not, because what puts you in a good situation is the season you have, which is not my problem. I think what puts you in a good situation is what they need and what they don't."