SAN DIEGO -- In recent weeks, the Red Sox have made their pitch to Jon Lester, both in person and through multiple discussions with agents Seth and Sam Levinson. Sometime before the Winter Meetings conclude Thursday, they should know whether the lefty will make a return engagement to Boston or sign with one of his other suitors.
The Cubs and Giants are two other teams heavily in play for Lester, and the Dodgers got involved last week. And you can never count out a mystery team such as the Yankees swooping in at the last instant. Lester's offers are all around $150 million over six years, FoxSports.com reported, with one unidentified team indicating it would be willing to go to seven years for about $175 million.
One report suggested the Red Sox had dwindled to remote underdogs for Lester. FOXSports.com's Ken Rosenthal tweeted on Monday afternoon, "Sources: Barring late change, Lester choosing between #Cubs, #SFGiants."
However, Seth Levinson responded swiftly, saying it was "completely untrue" that the Red Sox were out of the mix.
Red Sox general manager Ben Cherington added that he's heard nothing from Lester's camp to suggest his team was out of the running.
And Boston manager John Farrell went so far as to say he remained optimistic that Lester could once again list Fenway Park as his home baseball address for 2015 and beyond.
"I think we're still confident that we can sign Jon," said Farrell. "He's obviously going through this free-agency process. And as we came into this offseason, there were a couple of spots in the rotation that we needed to address and add to. And we're in the midst of that right now."
Farrell and Lester have a relationship that dates back to 2007. Farrell said he's been in contact with Lester three or four times this offseason, either by phone or text. And Cherington confirmed a report that owner John Henry visited Lester in the pitcher's hometown of Atlanta at the end of last week.
The one thing that seemed clear as of Monday evening was that the situation was on the verge of reaching closure.
"Oh, again, we're still optimistic that he'll be in a Red Sox uniform. There's a lot of history between the Red Sox and Jon," said Farrell. "We obviously have a strong desire to bring him back. And yet hopefully this is coming to a little bit of a head here."
Cherington stayed away from any predictions on which path Lester will choose.
"Jon will make a decision and he's sort of, as a free agent, has control over that process more than anyone else. I don't want to comment on speculate on anything other than we've been involved and other teams have too and it seems as though he's probably getting closer to a decision but that's all we know," said Cherington.
Once Lester signs, it could cause a flurry of activity with the rest of the pitching market.
And teams that don't sign anyone from that trio will surely be active in trying to trade for a pitcher. The Phillies' Cole Hamels, the A's Jeff Samardzija and the Padres' Ian Kennedy are among those who could be made available, and the Reds are believed to be willing to trade from their depth of pitching.
"But perhaps that'll start moving quicker [after Lester signs]," said Cherington. "I think there's been a lot of trade talk, not just with us, but with other teams too, and that's been going on for a while. I don't know if the two are directly related or not. I would think that deals will start to happen and then they'll speed up over the next several days."
Lester's future has been a topic of conversation since January, when he indicated he would take a hometown discount to stay with the Red Sox, as long as the offer was competitive. But after the Red Sox offered Lester a four-year, $70 million deal back in the spring, negotiations ended shortly thereafter.
"We desired to have a conversation with him and wanted to in Spring Training and wanted to during the season," said Cherington. "We were not able to have as much of one as we would have liked. There were reasons for that, and we understand and respected his desire certainly once we got into the season. So I think we wish we would have had a chance to talk more, whether it was in Spring Training or during the season. But, you know, that's behind us. We are now here, it's December, and it is what it is. We'll see what happens."
Lester was drafted by the Red Sox out of high school in 2002, and spent his entire career with the club until the deal that sent him to Oakland for Yoenis Cespedes on July 31.
Did the trade have any impact on the negotiations between Lester and the Sox this winter?
"It pushed it into free agency," Cherington said. "That's the only difference that I can tell. When you're in free agency, obviously, you're not the only team talking, so that's what changed. I don't sense any change in the relationship or our ability to communicate or anything like that. It's just he's a free agent and other teams are talking to him."
It is believed that it will take a contract offer of at least six years to sign Lester. Reports have surfaced of offers that have reached the $140 million range, but there has been very little in the way of specifics.
"Jon's going to go through this process as he needs to," Farrell said. "He's earned the right to get to this point in his career. And he's a primary target for a number of teams. And that speaks to his abilities as a player and as a pitcher."
Ian Browne is a reporter for MLB.com. Read his blog, Brownie Points, and follow him on Twitter @IanMBrowne. This story was not subject to the approval of Major League Baseball or its clubs.