ST. LOUIS – A deal that merited almost no attention at the time now stands as one of the best free-agent signings in Red Sox and even baseball history. 

No one cared much when the Red Sox signed Tim Wakefield to a minor-league contract on April 26, 1995, less than a week after he’d been released by the Pirates. Nearly 15 seasons later, that pact represents one of the great value signings of all time. (For a look at where his signing ranks in Red Sox free-agent history, see Wakefield in Perspective.)

Wakefield now has 175 wins with the Red Sox, third most in franchise history behind Roger Clemens and Cy Young (192 apiece). Since the advent of the modern free-agent system in 1976, only one pitcher (Greg Maddux, Braves, 194) has won more games for a team after moving to them as a free agent.

The idea that a team could have signed a player for little more than the league minimum and then gotten 15 years of successful service from him borders on preposterous. Yet that is precisely what has happened for Wakefield in Boston.

All of that raises a pair of questions: Just how was it that Wakefield was available in 1995? And why was it the Red Sox, among the 28 major-league clubs (Tampa Bay and Arizona had not yet been added as expansion teams), that acquired his services?

A GREAT START, A QUICK UNRAVELING

Wakefield was a sensation upon his major-league debut in 1992. He went 8-1 with a 2.15 ERA for the Pirates, finishing third in Rookie of the Year voting (to Eric Karros of the Dodgers and Moises Alou of the Expos) and becoming a key member of the playoff-bound Pirates staff.

In the postseason, Wakefield may have been even better. He had a complete-game victory in Game 3 of the NLCS between the Pirates and Braves, and another nine-inning W in Game 6 to force a winner-take-all seventh game.

“He basically dominated us,” recalled Sox pitcher John Smoltz, who was a member of Atlanta’s rotation that series. “I had to pitch Game 7. I was like, ‘I hope they don’t take him out (of Game 6). I know this guy can probably pitch on no days of rest. I thought they would bring him back. We couldn’t hit him.”

But as meteoric as his rise had been, his fall was perhaps even more sudden. In 1993, Wakefield entered the year as a starter in the Pittsburgh rotation. He went 6-11 with a 5.61 ERA, resulting in a demotion to Double-A, where he was even worse. Wakefield went 3-5 with a 6.95 ERA, then in Triple-A the following year, he suffered through a 5-15 campaign and 5.94 ERA.

“I just kind of lost my confidence. When you go from being celebrated in 92, winning two post-season games for them and carrying them through the NLCS to getting sent to Double-A it’s kind of demoralizing, I guess,” said Wakefield. “Then I had a clean-up surgery (for elbow bone chips) after the end of the ’93 season and I really wasn’t ready by the time spring training started so I went to Triple-A thinking I was only going to be there until I got healthy. I just wasn’t very good.”

The following spring, Wakefield had become almost an afterthought in Pirates camp. He made only one appearance in a major-league game, allowing 10 runs on eight hits against the White Sox. The Pirates released him.

“They have given me every opportunity to do what I could do, and I didn't do it. I think this is the best thing for the organization and the best thing for me,” Wakefield told reporters at the time. “I always said I wanted to finish my career in Pittsburgh. Maybe in my 28th year in the big leagues I can. I hate to leave Pittsburgh, but it's their decision. I have to respect that, and I do.”

For obvious reasons, that moment was a tremendously difficult one for Wakefield. In retrospect, however, the pitcher is able to consider it without any sense of remorse or discomfort.

“I only got to spend a little over a year (in Pittsburgh) as far as service time is concerned. I got to love the city. But not knowing what Boston is like, I’m glad it happened,” Wakefield said. “I think things happen for a reason, and I think the reason was for me to be here.”

“OFF THE SCRAP HEAP”

Coming out of spring training in 1995, the Red Sox rotation was in some disarray. With Roger Clemens sidelined, the team had been left to scramble, plugging pitchers like Rheal Cormier, Vaughn Eshelman and Frankie Rodriguez in for a few starts at a time.

So there was a realistic opportunity for a pitcher to sign at the end of spring training and find an entry crack into the rotation in Boston. That being the case, Wakefield agreed to sign a minor-league deal, with an assignment to Triple-A Pawtucket.

“We picked him up off the scrap heap. He was released and we gave him a second chance, which he deserved based upon how he pitched the first time around,” said former Sox G.M. Dan Duquette, who signed the pitcher. “He almost won the pennant for (the Pirates in 1992). He was one of their best pitchers and he worked fast and threw a lot of strikes with his knuckleball, which I liked. So I remembered that when he became available.”

In retrospect, it is almost surprising that virtually no one else even wanted to kick the tires. Wakefield was just two seasons removed from a year in which he was one of the most dominant pitchers in the game. Yet the pitcher recalls just one offer – a Double-A gig for the Orioles – aside from that made by the Sox.

It now seems fair to ask: if he had been a traditional pitcher, someone whose rookie success was predicated on a big fastball, would Pittsburgh have made him available? Would nearly every baseball team pass on the chance to sign him on the cheap?

“Probably not, but knuckleballers are an anomaly in the business,” said Duquette. “If you’re a knuckleballer, your confidence can be as fluttery as the pitch because so many variables go into your performance.

“Whether it’s an indoor stadium or an outdoor stadium, whether the wind’s blowing against you or it’s blowing from behind or it’s blowing from across, there’s so many variables that can affect your performance. If you don’t really have the skills, if you don’t really have the arrows in your quiver, it’s a very difficult row to hoe to keep confidence.”

That being the case, the Sox presented a unique opportunity to restore the pitcher’s path. Before shipping him to Pawtucket, the Sox first wanted the knuckleballer to head to their extended spring training facility in Fort Myers. There, by remarkable coincidence, Wakefield would have the opportunity for a unique tutorial.

The Sox were sharing their Fort Myers facility with the Colorado Silver Bullets, a women’s professional baseball team that was the first of its kind since the All-American Girls Professional Baseball League had folded following its lone year in 1954. The Silver Bullets had been formed in 1994 in response to the popularity of the 1992 movie “A League of Their Own.”

The team was owned by former Braves executive Bob Hope, who called upon former Atlanta pitching great Phil Niekro to manage the club. Phil Niekro not only agreed, but also sought out his brother, Joe, as the pitching coach.

And so, Wakefield had an opportunity to work with two of the finest knuckleballers of all time, a sibling tandem with 539 combined wins to its credit (318 for Phil, 221 for Joe).

“The Sox said we’ll send you to Fort Myers and you’ll get to work with Joe and Phil Niekro for about 10 days and then we’ll send you to Pawtucket,” said Wakefield. “It was pretty cool. The girls were pretty good and it was something that was breaking the barriers of gender stuff in baseball… I got a chance to work with (the Niekros) in the mornings before their workouts would happen.”

Though the association was relatively brief, it appeared to have a substantial payoff. Wakefield’s flagging confidence appeared restored by the opportunity to work with two of the pitch’s greatest practitioners and advocates.

“I think the time that Tim spend with Phil Niekro, who’s a Hall of Famer and head of the knuckleball fraternity, I think that served Tim well,” recalled Duquette. “Phil said ‘Timmy, you can pitch until you’re 45, and beyond if you want to with this pitch.

“Phil was a mentor to Tim and impressed upon him that the knuckleball is an out-pitch every time you throw it, and also encouraged him not to be discouraged on the days that he didn’t have perfect control of it because it was still an out-pitch whenever he threw it, even if the bases were loaded. I think that gave Tim a lot of confidence.”

There were other parts to the conversation: the significance of having an off-speed pitch, fielding the position, holding baserunners. Whatever the substance of the tutorial, it appears to have worked.

Wakefield went to Pawtucket, where he went 2-1 with a 2.52 ERA in four starts. That earned him a call-up to the majors, where he had an almost unfathomable run of success. In his first 16 starts, the knuckleballer went 14-1 with a 1.65 ERA. Just as was the case with Pittsburgh three years earlier, he was a key component of a Sox team that won the division.

A RED SOX MAINSTAY

But unlike Pittsburgh, where Wakefield was virtually a flash in the pan, the knuckleballer became a long-time fixture for the Red Sox. Only once in the last 15 seasons has he reached free agency.

That moment followed the 2000 season, when it seemed that the pitcher might not return to Boston. Wakefield recalled that the Sox were not going to offer him salary arbitration. But at the last minute, the Sox offered him a two-year deal with a team option for 2003.

“It came down to the 11th hour where they offered me another two-year deal to come back, and I couldn’t turn that down,” said Wakefield. “I could’ve become a free agent and tried to sign somewhere else but at that time I really wasn’t getting any offers before the deadline. I’m sure I would’ve gotten some after, but I wanted to come back here.”

That decision was further rewarded in and after the 2002 season. Wakefield, to his dismay, shuttled between the bullpen and rotation from 1999-2002 under managers Jimy Williams, Joe Kerrigan and Grady Little.

But Little and the Sox committed to making Wakefield a rotation fixture down the stretch in ‘02, and the organization made it a priority to sign the pitcher to a long-term deal that offseason.

“I really felt like I was a staple in the organization,” said Wakefield. “I had already gotten a sense that since the new regime had taken over that they viewed my loyalty to the Red Sox and my versatility as a pitcher at the time to how important I was to the club. I was also involved in some philanthropic things off the field that I really cared a lot about. They looked at that very deeply and they appreciated it.”

Wakefield, in turn, reciprocated that affinity. During the 2005 season, he made the extraordinary decision to sign a one-year, $4 million extension with a renewable team option that would allow the Sox to keep him at a relative pittance for as long as the team wanted to do so.

Now, Wakefield is 15 seasons into his Boston tenure, and performing as one of the better pitchers in the game. He is tied for the major-league lead with 11 wins in 2009, earning his first-ever nod in an All-Star game this year.

All these years after his Red Sox debut, the 42-year-old Wakefield continues to offer Boston remarkable return on the free-agent contract that he signed as a 28-year-old. What he has done during his tenure with the club is remarkable in its own right – a fact made evident by his climb up the franchise leader boards – but all the more so for the fact of how he came to the club.

Free-agent pitchers typically represent a terribly overpriced source of failure. Wakefield has been precisely the opposite.

“The value proposition, in terms of what you have to pay for the production you’re going to get on the free agent market, particularly as it relates to pitching, is generally a significant premium,” said Duquette. “But Tim is a unique pitcher, but we’re really finding out over the last year or so how truly unique he is, as he goes past Clemens for starts and starts to approach Clemens and Cy Young for victories.

“Tim fulfilled the prophecy that Niekro set for him,” he added. “He said, ‘Timmy, you can pitch until you’re 45 and if you want to stay in one place, you can do that, too.’ He told him all that.

“I think that because he goes about his job in a businessman-like way and has been here for so long, he doesn’t always get the credit that he could get, but he’s done a great job for the team.”