Though Beckett's performance level has gone up since he inked that last deal -- he led the Red Sox to a World Series championship in 2007 and has been a consistent workhorse for manager Terry Francona -- his motives for staying put remained the same.
"This is a very special place and I think that everyone who has had a chance to play here knows that," Beckett said. "The people who haven't had a chance probably know that through other people that have. I think this organization, they just do everything they can to make our jobs as easy as possible and from people I've talked to, there's not a whole lot of organizations out there that really do that. Whether it be in between starts or roundtable meetings, there's just a lot of things that go on here that make it a very ideal situation for a baseball player."
The Red Sox, knowing that Beckett is a fierce competitor every fifth day and a relentless worker in the four days in between, had no interest in watching him slip away.
"We couldn't be more thrilled to keep Josh around," said Red Sox general manager Theo Epstein. "We were just talking about the fact that it will be nine years as a Red Sox when this contract is up. He's earned it. Josh is an excellent contributor on the field and off the field to this organization. He's a big part of our team and our pitching staff and it means a lot for us to have the stability, knowing he'll be here for a long time leading this staff."
It is a staff that is now loaded for not just this year, but for the next several. Not only do the Red Sox have contractual control over Beckett through 2014, but also Jon Lester, John Lackey and Clay Buchholz.
"Well, it feels good," said Epstein. "It's hard to have an elite organization without excellent starting pitching. I think we have an even higher standard here. We need starting pitching that can succeed in the American League East and against these tough lineups that we face night in and night out. When you have that pitching, you don't want to let it get away. It's hard to acquire in free agency, it's hard to acquire in trade, and it's hard to draft and develop this kind of starting pitching."
So when Epstein signed Lackey for five years at $82.5 million back in December, he immediately sent Beckett a text message to let the ace know that his long-term future with the team was still a high priority. Epstein and his staff turned that into action, holding some talks with Beckett's representatives this winter and hammering out most of the new deal during the final stretch of Spring Training.
"It's pretty easy when you have a strong desire to retain the player and the player has a strong desire to stay in the city," said Beckett. "Those things tend to get done."
Because A.J. Burnett signed for five years a year ago and Lackey did so in December, there was some thought that Beckett would similarly want a contract of that length. Whether he did or not, it didn't become a sticking point.
"I guess I look at it differently than most people do," said Beckett. "A lot of people look at what you can lose or what you lost and I look at what I gained here. I gained four years more of stability knowing that I'm going to be in an organization that's going to put a competitive team out there every year. And that really can't be underestimated either, because the season gets really long when you're losing 90 games. Whenever you've got a chance to win 100 games every year, the season goes by a little faster. I know I'm going to have a chance to win every year here. For me, I look at it more for what I gained than what I potentially lost."
And, as Epstein noted, the way the timing of this deal happened, the Red Sox essentially have made a five-year commitment in Beckett. Did Epstein and the Red Sox fear that the lack of a fifth year in the extension could become an obstacle?
"I thought it could have been. It's always up to the player," Epstein said. "The fifth year is not something we would have done at this early date. We're basically going a year early. We're taking a risk of five years, even though it's only a four-year extension. Players often have to decide if they want to maximize years and dollars and wait all the way to free agency to get that reward or whether they want the security of a contract now. When you do a contract early, often times the club wants some type of a discount, whether it's years or dollars and I think this is a very fair contract for both sides."
Health projection is always something a club labors over in a contract of this magnitude. In Beckett, the Red Sox know they have a pitcher who will do everything in his power to keep his shoulder strong.
"We have outstanding health reports," Epstein said. "All the testing now [on Beckett] is better than it's ever been. I think the commitment we made today demonstrates that. We kind of put our money where our mouth is. He's a guy that's insurable. He's a guy that we count on to be as healthy as he's been. And look at what he's done for us. He's been remarkably consistent throwing as many innings as anybody and there's not a medical reason why that shouldn't continue with the work he's put in to create a foundation for success health-wise."
Beckett appreciates being that guy the Red Sox can count on for durability and performance.
"I think you've just got to put yourself in the best possible position," said Beckett. "I think that the work that not only myself, but also the trainers and the strength coaches do, puts me in that situation. I think the thing that the Red Sox see is they're not worried about me skimping on things that make me healthy. That's where the health comes in."
Beckett's contract was finalized the day after he struggled against the Yankees on Opening Night, giving up eight hits and five runs over 4 2/3 innings. The Red Sox went on to win the game, 9-7. He will take the ball next on Sunday in Kansas City.
Beckett, who will turn 30 on May 15, is 65-34 with a 4.07 ERA in 123 starts for the Red Sox. He is 106-68 with a 3.81 ERA in his career, which began with the Florida Marlins in 2001. He had an October for the ages in 2007, going 4-0 with a 1.20 ERA to lift the Red Sox to a World Series championship. Beckett was similarly heroic in leading the Marlins to a World Series title in '03, firing a shutout against the Yankees on three days' rest in the Series-clinching Game 6.
He was acquired by the Red Sox in November 2005 in a blockbuster trade that also brought Mike Lowell to Boston. Hanley Ramirez, now one of the best all-around players in the game, went to Florida in that deal.
With two World Series rings already tucked away, Beckett would love to add some more to his collection.
"I think that's what we're all striving for every year," Beckett said. "It's a very difficult thing to attain. I would say that with this organization, I think we have a chance to win a ring every year. I've only been on one team here  that didn't make the playoffs. I haven't been on one team here where I didn't think we could win the World Series at the beginning of the season. That's pretty remarkable to think ... this is my fifth season here now, and at the beginning of each year, I really had a strong feeling that we could win the World Series."