It wasn’t supposed to be this easy, but it was. Why? Because the Red Sox really like Josh Beckett. It’s that simple.

Monday, after tying up a few loose ends, the Red Sox announced the signing of Beckett to a four-year contract extension worth $68 million (annual salaries of $15.75 million from 2011-14 with a $5 million signing bonus baked in). Done. Yet another starter now carrying a contract of four or more years, giving the Sox more than any team in baseball.

This was supposed to be complicated. It wasn’t.

In the end, the negotiations weren’t all that out of the ordinary. Beckett came in with a high figure -- asking upwards of Carlos Zambrano’s five-year, $91 million deal that includes a vesting option for another $19.25 in 2013. That’s what you’re supposed to do.

The Red Sox requested some sort of medical contingency for the back-end of the extension, offering a financial bump in exchange for the security. That’s what they like to do.

Beckett told his agent, Michael Moye, what he was ultimately looking for at different stages of the negotiation, and not to call unless the Red Sox got close to those parameters. A few phone calls later, the team was holding a press conference.

Simple.

The reasons why it shouldn’t have been so seamless first were uncovered a few years ago and stretch all the way to the day Red Sox general manager Theo Epstein text messaged Beckett after signing up John Lackey. Here’s a timeline that led to skepticism:

2005: Beckett turns down the opportunity to secure an insurance policy after he was told it would include coverage on every part of his body but his right shoulder. "I ended up not getting it because I'm a major league pitcher," he said during a spring training interview. "I didn't want them to insure my face." It marked the initial concern regarding Beckett’s shoulder, a body part that has since not been identified as a problem during his tenure with the Red Sox.

2006: Beckett signs a three-year, $30 million contract extension. The deal was struck not only at a time when the pitcher was struggling in his first season with the Red Sox, but at a time when he may have still had some insecurities about not having been able to secure insurance a year earlier.

2007: Johan Santana signs a six-year, $137.5 million deal with the Mets. The reason this was significant was because if Beckett hadn’t signed his previous extension, this was the same kind of contract for whcih he could have been in line following a momentous ’07 season. And while the Sox had signed Daisuke Matsuzaka to a six-year deal, the organization was reluctant to commit the kind of years Santana had secured to any pitcher, never mind one with medical question marks with which the team was intimately familiar.

2008-09: While the shoulder still wasn’t an issue, enough aches and pains had cropped up with Beckett throughout the two seasons (back, numbness in his arm, etc.) that might have given the Red Sox some pause when committing to the almost-30-year-old.

2009: The Jason Bay negotiations. It was learned that the Red Sox had drawn back on a four-year, $60 million deal due to medical concerns, having asked the outfielder to accept a deal with medical contingencies. It was thought by some that if the Sox were going to be hesitant about signing an outfielder because of medical issues -- particularly medical issues that were viewed as non-threatening for the life of the contract by other doctors who offered second and third opinions -- the Red Sox would surely throw up a litany of red flags when it came to evaluating Beckett’s long-term viability.

2009: Lackey signs. Once word came down that the pitcher -- whose age and statistics compared favorably with Beckett -- had been awarded a five-year deal, it was natural to conclude that the Sox wouldn’t possibly dish out a similar deal to yet another starting pitcher. Few thought the Sox would commit to five years with Beckett to begin with, and with Lackey aboard it seemed as though the organization might view the presence of their Opening Day starter as a luxury until it was time to turn over the top of the rotation at year’s end.

So, why did all of this get pushed aside, leading to a starting staff with 20 years of club contractual control (not including Clay Buchholz)? Because Beckett convinced the Red Sox that he was worth it.

First came the evolution of Beckett as the leader for not only the Red Sox’ current staff, but for an entire organization of young pitchers. The hurler has developed a process that lends itself to success, one that has already paid dividends. Jon Lester, for instance, is a byproduct of embracing Beckett’s way of approaching each start, and Buchholz seems to be getting it, as well.

"What I would tell our young pitchers is, ‘Look at Josh, and look at the reasons we signed him.’ Yeah, it’s for his performance on the field, but it’s also for the way he goes about his business and how important routine is to him, how much he cares about preparation, how much he cares about his teammates, how he prioritizes winning over his own individual performances. That’s the model," said Sox general manager Theo Epstein. "We already do that. We tell our minor leaguers in their first year in big league camp, like Casey Kelly this year, watch Josh Beckett, watch Jon Lester, and learn the difference between being a guy who just goes out and takes the mound every five days and being a starting pitcher for the Boston Red Sox.

"If you want to succeed in the American League East, there’s a lot more that goes into it than just toeing the slab every five days. There’s a lot of mental, physical and fundamental preparation and work that’s required. [Beckett] is a great example of how to do it the right way."

And then there were the physicals. Beckett took both physical examinations administered by the team and an insurance company, passing both with little problem. They not only led to his current deal getting done, but also the ability to secure the personal insurance policy that had eluded him following the ’05 season. 

"We have outstanding health reports. … All the testing now is better than it’s ever been. The commitment that we made today demonstrates that," said Epstein. "We kind of put our money where our mouth is. He’s a guy who is insurable. He’s someone who 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. He’s thrown as many innings as anybody. There’s not a medical reason why that shouldn’t continue with the work that he’s put in to create a foundation for his success health-wise."

There was also the matter of what the Red Sox would do if Beckett had left following ’10. As Epstein pointed out, the likelihood is that there will only one top-of-the-rotation pitcher [Cliff Lee] available on the open market following this season, and while optimism abounds regarding Lester, Lackey, Buchholz, and even 20-year-old Casey Kelly, there is always the possibility that keeping up with the Yankees means somehow getting one more ace.

In the end, it all worked out for both sides when few thought it would. Who knew? Not the Red Sox or Beckett ... until Monday.