FORT MYERS, Fla. – Jon Lester may be going where no pitcher has gone before.

Yahoo! Sports reported on Sunday that, according to a source close to the Red Sox, Lester has signed a five-year, $30 million deal with a $13 million option for the 2014 season. Red Sox officials, including CEO/President Larry Lucchino, GM Theo Epstein and manager Terry Francona, all declined to confirm, deny or comment on the report.

Earlier this spring, however, the pitcher made clear his desire to remain a Red Sox for the long haul.

“This organization,” said Lester, “is special to me and to my family. They’ve done a lot for us. The people in it have treated us very well.”

“I don’t see myself playing elsewhere … I’d love to stay here for the rest of my career if I can,” he added. “If the topic (of a long-term deal) comes up, we’re definitely going to sit there and listen and try to get something done. I’d love to be here for a very long time and have that security. When it comes up, hopefully we can get something done and be set.”

Lester acknowledged at the time that a long-term deal would necessarily involve a form of risk-sharing with the Red Sox, and that players need to sacrifice some dollars in exchange for both financial security and greater geographical stability. The left-hander made clear that he was open to those compromises to remain with the team that drafted him in 2002.

“Both sides win,” Lester said. “The young guys get money that’s going to set their families for the rest of their lives. They get the security. They know where they’re going to be at.

“It’s nice to see (teammates Dustin Pedroia and Kevin Youkilis get long-term deals). It’s probably nice for a lot of these other younger guys to see that the Red Sox care that much about their young guys to lock ‘em up. I think it’s good on both sides. They’re not spending free-agent money to get other guys. These guys are taking the right discounts and the Red Sox are giving them the right amount to be here for a long time.”

Now, it appears that Lester will be joining his teammates. If the reported terms are accurate, the deal would not only keep the 25-year-old pitcher in a Red Sox uniform through his 20s, but also represent the biggest commitment ever made to a pitcher at Lester’s career stage.

Lester has slightly more than two years of major-league service time. He is still a pre-arbitration player to whom the Sox can assign any contract value above the major-league minimum ($400,000) that they see fit. It would not be until after this coming year that Lester could secure a big payday through the arbitration process. Apparently, that timetable is about to change.

Never before in major-league history has a pitcher with Lester’s experience been given a contract with more than a four-year guarantee. Lester, if the report is accurate, will get five.

Never before in major-league history has a pitcher with Lester’s major-league service time been given a guarantee of more than $15 million. The left-hander will double that amount.


























AN ANSWER FOR EVERY QUESTION

That Lester would receive these sorts of unprecedented guarantees is startling. It was just over a year ago, after all, that Lester was hoping to demonstrate his abilities over the course of a full baseball season for the first time in his major-league career.

Most of the baseball world had little idea what to expect from the pitcher. Questions loomed as to whether he would ever recapture the immense promise he demonstrated during his journey through the minors, which was interrupted by cancer in his first major-league season.

Those questions were answered in remarkable fashion. Lester was the ace of the Red Sox staff last year, going 16-6 with a 3.21 ERA in 210 regular-season innings. He followed that by recording a 2.36 era in 26 postseason innings.

A common refrain crept up among talent evaluators from other clubs, more than one of whom suggested they had no idea that Lester would be so dominant, so quickly. Baseball officials were not alone in marveling at Lester’s emergence.

“I’m not blown away by too much. But I love watching playoff baseball if I’m not in it,” John Smoltz said upon his arrival in spring training. “What these guys have done, especially Jon Lester, what he did last year, I just sat there with my mouth open. At that time of the year, you’re not supposed to be doing what he did.”

LESTER TO BE IN A CLASS BY HIMSELF

Presuming that the Yahoo! report accurately represents the terms of a potential deal, the Red Sox are paying Lester as if he is indeed a rare breed.

Since 2005, there have been six pre-arbitration pitchers signed to long-term deals after two-plus seasons: Cliff Lee (4 years, $15 million), Adam Wainwright (4 years, $15 million), Jake Peavy (4 years, $14.5 million), Chris Young (4 years, $14.5 million), Scott Baker (4 years, $14.5 million) and Jeff Francis (4 years, $13.25 million).

All of those pitchers except Wainwright have offered the club a one-year option that would buy out their first year of free agency for $7-9.25 million. Wainwright gave the Cardinals options on his first two free-agent years, valued at $9 million and $12 million.

A five-year, $30 million guaranteed contract, then, would guarantee Lester $6 million more than any of those peers through his first free-agent year. The Sox would be placing more trust (as defined by guaranteed dollars) in Lester than any other club for any other pitcher who had not yet reached arbitration eligibility.

So why would Lester get such a bump?

Either he is viewed as a pitcher who has separated himself from other pitchers with two-plus years of service time (unlikely, given that both Lee and Peavy have won Cy Youngs) or that other contracts are influencing his.

The latter scenario appears more likely. It would seem that a few contracts represent key markers for a long-term deal for Lester.

Indians pitcher Fausto Carmona, after just more than a year of big-league service, signed a four-year, $15 million deal at the start of 2008. The deal could be worth up to $36 million for the guaranteed term of Lester’s contract (if the Indians exercise a pair of options to buy out one free-agent year), and up to $48 million total (as compared to $43 million for Lester) for a second year of free agency.

Left-hander Cole Hamels, who won the World Series MVP for the Phillies this October, offers another point of comparison. Hamels, who has played just under three seasons in the majors, was arbitration-eligible for the first time this winter.

The Phillies will pay the pitcher $20.5 million over the next three years. For a five-year, $30 million deal, the Sox would pay close to but slightly less than that amount for Lester’s arbitration years.

Angels pitcher Ervin Santana, who went 16-7 with a 3.49 ERA last year and was arbitration-eligible this winter after reaching more than three years of service in the majors, signed a four-year, $30 million deal this offseason. The deal bought out one year of free agency, and also featured a $13 million club option that is identical to the one that Lester has reportedly offered.

For all intents and purposes, Lester’s deal matches that of Santana. Long-term deals for pitchers with comparable service time usually offer a low salary (less than $1 million) in the first season, suggesting that Lester’s arbitration-eligible and free-agent seasons are valued almost identically with Santana’s.

That in itself would represent a coup for the Red Sox pitcher, since the earlier a player signs a long-term deal, the less money he typically gets, since there is less data about his long-term performance.

“I think it is quite a leap of faith, but could save (the Sox) money in the long run,” one executive of another club suggested. “The obviously believe in Lester.”

A TWO-WAY STREET

Even so, while the Sox may be willing to give Lester top dollar for his service class, the team still would stand to benefit from such a long-term deal. Lester has the potential to make piles of money through the arbitration process given some of his markers of career success.

Lester is 27-8 in his big-league career, and his .771 winning percentage ranks as the best of all time for pitchers with at least 25 starts. Last season, he vaulted to elite status, becoming one of just seven pitchers this decade who, at age 24 or under, won at least 15 games with a sub-4.00 ERA in one of his first three seasons.

Such pitchers can make quite a bit by going year-to-year. Cubs pitcher Carlos Zambrano, for instance, made roughly $22.6 million with three one-year deals during his three arbitration years.

Moreover, Lester’s free-agent year could end being a bargain should this year’s market, in which Derek Lowe received $15 million per year, A.J. Burnett got an average annual value of $16.5 million and CC Sabathia received an average of $23 million per year.

In many ways, Lester’s profile is similar to that of Cliff Lee at the time that he signed his four-year, $15 million extension. The Indians left-handed had about 2.5 years of big-league service and was coming off a year when he won 18 games and had a 3.79 ERA when he signed.

In 2007, the deal looked like it might represent an albatross when Lee had to be sent to the minors in a year when he went 5-8 with a 6.29 ERA. Last year, however, he turned in easily the most dominant season in the American League en route to the Cy Young.

Cleveland will retain his services for the bargain rate of $5.75 million for what would have been his final year of arbitration eligibility. Assuming Lee does not get injured, the team’s $9 million option for his first free-agent year in 2010 will also represent excellent value.

“Any multiyear deal for a pre arb player is about sharing risk,” Indians G.M. Mark Shapiro, who reached deals with both Carmona and Lee, explained in an email. “In every case, we are attempting to find a value that both the player and team will feel good about over the length of the deal while being very upfront that we are both risking something in the deal – the team overpaying due to injury or an unexpected drop in performance, and the player risks leaving money on the table that he would make in arbitration going year to year healthy with consistent performance. 

“We attempt to find that value that works for both sides but are also comfortable if the player prefers to go year to year. The defined risk is different for every player and is certainly greater incrementally from position players to starting pitchers to relief pitchers.”

Lester, the Sox seem to have concluded, is a player and person worthy of such a risk. For his part, the pitcher has concluded that he does not want to leave his club, a commitment that is worth some potential financial sacrifice of his own.

The apparent result is a deal unlike any other in major-league history. Of course, Lester’s career path has also been unique in big-league annals, and so perhaps it is only fitting that he might receive a contract that reflects that fact.