FORT MYERS -- As he enters retirement following a 19-year major league career that netted 200 victories, there are any number of ways to understand the career of Tim Wakefield.

The knuckleballer was a story in perseverance, having resurrected his career in 1995 after he thought his time in baseball might be at its end following his release by the Pirates.

He was a study in longevity, consistency and endurance, traits that allowed him to move up the franchise leaderboard in numerous categories. Though he never did eclipse Roger Clemens and Cy Young for the franchise record in wins, as Dan Duquette -- the former Red Sox general manager who signed Wakefield to a minor league deal in 1995 -- noted, he is tops in franchise history in innings thrown and, hence, outs recorded.

When he volunteered to sacrifice his Game 4 start in order to pitch in relief for an overtaxed bullpen in Game 3 of the 2004 American League Championship Series, Wakefield became a study in self-sacrifice for the team good.

Wakefield’s impact off the field and in the community was vast as well, something that earned him recognition in 2010 as the Roberto Clemente Award winner for contributions on and off the field.

But in many respects, one trait characterizes Wakefield more than any other. A compelling case can be made that the 45-year-old was the most loyal player in modern Red Sox history, a notion underscored by a one-of-a-kind contract that he signed in 2005.

For Wakefield, the attraction of being a member of the Red Sox was nearly instantaneous after he signed with the club in 1995 following his release by the Pirates. He thought that his career might be over when Pittsburgh consigned him to the scrap heap, and so when he first entered Fenway Park as a member of his new club and went on a magical 14-1 run that summer to start his Boston career, he could be forgiven an instant sentimentality.

Wakefield's first appearance in Fenway Park as a member of the Red Sox was indeed unforgettable. It was June 4, 1995, and he ended up throwing a 10-inning complete-game, guiding the Red Sox to a 2-1 victory over the Mariners. For Wakefield, the day was breathtaking for reasons that had little to do with the box score.

“[The feeling of wanting to retire with the Red Sox occurred] the first time I stepped out of the dugout in ’95 and saw the Green Monster. Honestly," Wakefield said. “Just being part of such a historic franchise, I knew it the first year I put this uniform on that this is where I wanted to retire and this is where I wanted to spend the rest of my career, however long it was going to be.

“You never know when you’re that young in your career how long your career is going to last, but I knew [it] once I put this uniform on.”

That said, Wakefield also was a realist. He recognized that the world of modern baseball free agency works two ways, and that a player does not have complete control over the team for whom he will play.

“There were some years there,” Wakefield acknowledged, “where I didn’t know if I was going to come back or not.”

In early 2005, Wakefield was nearing the end of a three-year, $13 million contract he’d signed following the 2002 season. He was in the 11th year of his improbable run with the Red Sox, and he wanted to take any guesswork out of where he would spend the rest of his career.

He and his agent, Barry Meister, were hoping to engage the Red Sox in dialogue about a contract extension. The Sox valued Wakefield -- at age 38, he represented a durable presence in the rotation, someone who would reliably take the ball every five days and more often than not give his team a chance to win -- but it was still early in the year, and mindful of the various elements (injury, performance decline) that can befall players, the team was a bit reluctant to advance talks of an extension too aggressively.

But Wakefield had no desire to leave any gray area about his future. His baseball home was Boston. He wanted to do everything in his power to avoid even the possibility of changing teams. That, in turn, led to the following conversation, as recounted by Meister yesterday:

Meister: “When you’re going to be a free agent, signing with the Red Sox is going to be a combination of your interest in staying and their interest in keeping you, and sometimes their interest in keeping you. Sometimes whether you stay with a team isn’t just affected by what happens to you. There are trades the year before; there are free agents.”

Wakefield: “Well, what if we just stay ahead of the curve, sign a contract that we can talk about in July and August of each year and then just extend the process?” 

Meister: “OK, I can build that concept but it’s going to cost you money.”

Wakefield: “Is it more or less likely I’ll be a Red Sox if we do it?”

Meister: “Again, more, but there’s a price.”

Wakefield: “Do it.”

“That,” Meister concluded, “is how it came about.”

Meister told the Sox that Wakefield was amenable to a contract structure that had an option built in. Indeed, according to one person familiar with the talks, the agent suggested that Wakefield would give his team “an option forever.”

The Sox took the idea literally, and worked with Meister to create a contract that had never been seen in the era of modern free agency and that has not been enacted since. Wakefield agreed to a one-year, $4 million deal for the 2006 season (itself, as Meister suggested, a relative bargain for the Sox given that the market value of durable starting pitchers was perhaps millions more than that) that included a recurring $4 million team option.

If the Sox wanted to retain Wakefield for the 2007 season and exercise his option for that year, they would get another team option at the same $4 million base salary for 2008. If they exercised that, they would get another $4 million team option for 2009.

In short, Wakefield waved off the opportunity to seek market value for his services and ceded control of his contract completely to the team in order to do everything in his power to ensure that he would remain a Red Sox for life. It was a stunning contract that, in some ways, hearkened back to the days when players were controlled by teams in perpetuity under baseball’s reserve clause, a system that was struck down (thus spawning the era of modern free agency) in December 1975.

The uniqueness of the contract was such that there was uncertainty about whether the Major League Baseball Commissioner’s Office or the Players Association would approve it.

“It really does show what this guy’s priority was. His priority was to remain a Red Sox. He expected when he signed that contract to pitch for a long time,” Red Sox assistant GM Brian O’Halloran recalled. “Clearly, his priority was remaining a Red Sox. That says a lot. It’s impressive. And the feeling was mutual.

“It was unheard of, and hadn’t been done before or since,” O’Halloran added. “It’s always impressive when a player or someone in any walk of life makes a decision based on things that are more important than money. Obviously he put a lot of thought into it. They were looking for ways to make sure he stayed a Red Sox. It was creative.

“I remember thinking at the time, ‘Wow, that’s amazing that he wants to do that.’ … It helped carry the relationship this far and a lot of good things happened in this time.”

The sacrifice was particularly significant since Wakefield enjoyed one of the greatest seasons of his career in 2005. At age 38, he went 16-12 with a 4.15 ERA and a career-high 225 innings, serving as the de facto ace of the Sox pitching staff that year.

Had he reached the market that offseason -- a winter when Kevin Millwood received a five-year, $60 million deal, A.J. Burnett was given a five-year, $55 million contract and Jarrod Washburn received a four-year, $36 million contract -- Wakefield might have been able to double the annual salary he received from the Red Sox with his extension. But that matter was secondary.

Wakefield wanted to remain with the Red Sox, and his contract helped him ensure that he would do so. The team exercised its option three times (for the 2007, 2008 and 2009 seasons) and then, after the 2009 season, negotiated a new two-year, $5 million deal with Wakefield that included various incentives for the number of games started.

With six more years in Boston, Wakefield won a second World Series with the club, was named to his first All-Star Game in 2009, reached 200 career victories and set a record for the most seasons spent pitching for the Sox. And on Friday, he was able to retire not only as a Red Sox, but as someone for whom it was unimaginable to be anything but a Red Sox.

“Honestly, we had four separate clubs call about him this offseason. I said, ‘Do you want me to play the agent game, the what-if game? I know one of them wants to offer you a major league contract,’ ” Meister noted. “He said, ‘No, I’m going to retire a Red Sox one way or the other.’ ”

And so, Wakefield spent the offseason weighing the question of whether to return to the Sox on a minor league deal and compete for a job in big league camp or to finish his career. To his mind, even with offers from other teams, there was no third choice.

Ultimately, Wakefield said on Friday, he felt that for both his family and the good of the Red Sox, it was time for him to step away. But his departure struck all the right notes, and occurred in an appropriate setting for a player whose actions were those of a player who is worthy of the title of the Most Loyal Red Sox of the free agent era.

Some players speak of loyalty, but none has ever put his money where his mouth is in the fashion that Wakefield did. He went to extremes to avoid the open market, and as such, his career concluded in precisely the way that he had hoped ever since he first glimpsed Fenway Park.

“I never wanted to pitch for another team. I always said that I wanted to retire a Red Sox, and today I'm able to do that,” Wakefield said. “I’m very grateful I've been able to put this uniform on for such a long time, and win two World Series for this great city. Now I can finally say it’s over.”