Jon Lester heard another pitch for his services Monday, meeting with the San Francisco Giants, who can show off three World Series trophies won in the past five years as evidence that if it is winning the pitcher treasures most, there are worse places to go.
The Giants also have some reserves of cash, having been beaten out by the Red Sox for the services of their popular third baseman, Pablo Sandoval, who signed a five-year, $98 million deal with Boston last week. Lester doesn't have a nickname to rival that of the Kung Fu Panda -- he doesn't have a nickname, period -- but he can offer a persuasive case that he gives the Giants a better chance to return to October than Sandoval could.
The Giants are the fourth team Lester is known to have met with, joining the Red Sox, Chicago Cubs and Atlanta Braves. Lester's agent, Seth Levinson, has not identified whether there are remaining stops on Lester's tour, but with the winter meetings opening next Monday in San Diego, there are certain to be critical conversations with the known suitors and a possible unknown (Yankees?) before the courtship phase gives way to decision time. That decision, as Levinson repeatedly has reminded inquisitors, could come at any moment, although it would surprise no one if the contenders for his services get a final chance in San Diego to sweeten their offers.
John Hart, the Braves' director of baseball operations, signaled that his team is not in contention when he told MLB Network Radio that Lester was the "right person at the wrong time" for the Braves. The Giants are a late entry for Lester, the Cubs are employing a full-court press, and Red Sox owner John W. Henry indicated last week that his team would be willing to exceed the luxury tax threshold in its pursuit of pitching.
How high will the bidding go for Lester? Baseball Prospectus recently noted that there have been only seven $100 million-plus deals for free-agent pitchers since Kevin Brown signed the first in 1998, and only two of those pitchers, Brown and Cliff Lee, were past their age-30 seasons when they signed.
But of that group, only two pitchers had a higher ERA+ in their walk year than Lester's 155 (Brown 164 and Sabathia 156), which only reinforces the belief that Lester will command top dollar. He won't approach Clayton Kershaw territory ($30.7 million average annual value), but considering where the next tier is -- Sabathia ($24.4 million AAV), Cole Hamels ($24 million) and Lee ($24 million) -- the $25 million area is certainly feasible.
Will the Red Sox go that high? They went to a $22 million AAV last week for the oft-injured Hanley Ramirez, who like Lester is entering his age-31 season. But he will be playing a new position, left field, and trying to reverse a trend in which has missed 185 games over the past four seasons. Given that precedent, Lester and agent Levinson are doubtful to embrace a significant hometown discount. The Red Sox are willing to go to six years, but a six-year, $132 million deal might represent more a base-level offer than ceiling for Lester.
The Sox are prepared to explore other pitching options if Lester chooses to go elsewhere, and have several factors working in their favor:
• They have the two commodities in the greatest demand on the trade market -- productive bats and young pitching under contractual control.
• There are a number of quality pitchers who are one year away from free agency, making their teams more apt to consider dealing them.
• They have boatloads of cash.
Hamels remains the most obvious target if the Sox fail in their pursuit of Lester. The Phillies are in rebuilding mode, Hamels is just days older than Lester, has proven just as durable (200 innings or more in six of the past seven seasons), has thrived in a market (Philadelphia) as demanding as Boston and is coming off a season in which he posted a career-best ERA+ (151).
The Phillies want premium prospects in return, which could mean the Sox will be asked to part with Mookie Betts or Henry Owens, just as they did nine winters ago when they traded their best prospect, Hanley Ramirez, plus pitcher Anibal Sanchez, to the Florida Marlins in the deal that netted them Josh Beckett and Mike Lowell. The Sox won the World Series two years later, and owner Henry last week might have offered a hint at his willingness to give up prospects if necessary when asked about the team's worst-to-first-to-worst performance in the past three years.
"If I could go to the World Series every other year,'' he said, "I'll take it.''
One way general manager Ben Cherington could avoid surrendering his best prospects is if he could engage a third team in trade talks with the Phillies, which would lessen the hit the Sox would take. Former GM Jim Bowden, writing on ESPN.com, proposed just such a scenario involving the Cincinnati Reds, who would wind up with veteran outfielder Yoenis Cespedes while combining with the Sox to offer prospects that would net Hamels for the Sox. Purely speculation, but the Sox are hardly averse to considering multiteam proposals.
The Reds and Red Sox might find they match up directly. GM Walt Jocketty has three quality pitchers a year away from free agency -- Johnny Cueto, Mat Latos and Mike Leake -- and is looking for offense. Cueto might be off the table, but a package built around Cespedes and perhaps Allen Craig could entice the Reds for Latos or Leake.
The Padres have a new GM, A.J. Preller, who offered Sandoval more years than he got from the Red Sox and also made a strong run at Cuban slugger Yasmani Tomas before he signed with Arizona. Preller needs help for the offense-starved Padres, and he has a right-handed free-agent-to-be, Ian Kennedy, who matches up well financially with Cespedes, who is owed $10.5 million in 2015. Kennedy, who struck out 207 batters in 201 innings, is projected to approach that figure in salary arbitration.
Oakland GM Billy Beane, who last Friday traded his All-Star third baseman, Josh Donaldson, in a stunning deal with Toronto, has demonstrated time and again his willingness to trade anyone on his roster. Could that possibly include ace right-hander Sonny Gray? It seems preposterous to even mention it, unless the Sox were willing to build a package around Xander Bogaerts.
Beane already has fielded inquiries for Jeff Samardzija, the right-hander who cost him his top prospect, Addison Russell, in a trade-deadline deal with the Cubs. The Athletics and White Sox are talking about a Samardzija deal that would gain Oakland shortstop Alexei Ramirez in return, but the Red Sox are known to have an interest.
Other potential targets include Jordan Zimmermann, the Nationals' top pitcher, Mets left-hander Jon Niese and perhaps Tigers right-hander Rick Porcello (Zimmermann and Porcello are a year away from free agency, Niese is signed for 2015 and '16 with team options for '17 and '18). The Sox are not expected to make a run at free agent Max Scherzer, who turned down a six-year, $144 million offer from the Tigers last spring, but free-agent right-hander James Shields remains a potential fallback plan.
The Red Sox, remember, prefer to come away this winter with two pitchers to slot at the top of the rotation. But the number of true aces remains few, and Lester still figures as the ideal solution.