Jon Lester Will Sign With Cubs, Pitcher Decides, Snubbing Boston Red Sox [UPDATED]

Jon Lester, the most sought-after free agent pitcher on the market this offseason, is expected to commit to a deal with the Chicago Cubs, an organization headed by former Boston Red Sox General Manager Theo Epstein, according to various baseball sources on Tuesday night.

But Lester’s original team, the Red Sox, believe they are still in the chase for Lester, who was expected to make a decision on his future home by Tuesday — at this point, however, the pitcher may not be able to make up his mind until sometime Wednesday, reports say.

UPDATE 2:30 am EST: Jon Lester has announced that he will sign a contract with the Chicago Cubs, rejecting the team that drafted him and with which he won two World Series rings, the Boston Red Sox. His contract will reportedly pay him $155 million over six years.

The reigning Major League Baseball champion San Francisco Giants, the only team other than the Red Sox to win three World Series titles since the turn of the century, have also made an offer to Lester, as have their hated rivals, the Los Angeles Dodgers — but a Giants official, assistant GM Bobby Evans, said on Monday that he felt that both the Giants and Dodgers had already missed out on signing Lester.

AGM Bobby Evans #Giants leads us to believe that Lester has both Red Sox and Cubs ahead of them & Dodgers @MLBNetworkRadio

— Jim Bowden (@JimBowden_ESPN) December 9, 2014

The Giants now believe that the 30-year-old Tacoma, Washington, native will opt either for the Red Sox — the team that drafted him since 2002 and that developed him until he was dealt to Oakland at the 2014 trading deadline — or the Cubs, where Lester has close personal ties to Epstein and General Manager Jed Hoyer, another former Red Sox executive.

But even as the sun set on Tuesday, the day when Lester was allegedly going to issue his decision, conflicting reports were emerging from Lester’s camp. According to ESPN veteran baseball reporter Buster Olney, Lester will have full details of all four offers in front of him by Tuesday night and could make his call before retiring for the evening. Another ESPN writer, longtime Red Sox beat reporter Gordon Edes, agreed with Olney’s assessment.

By tonight, Lester will have all info in front of him to make decision

— Gordon Edes (@GordonEdes) December 9, 2014

But a report out of Boston from another Red Sox beat writer, Rob Bradford of WEEI.com, said late Tuesday that Lester’s agents did not yet feel ready to hand over documents regarding the four offers to the ace southpaw at his home in Atlanta.

According to Bradford, Red Sox brass met with Lester’s agents again on Tuesday afternoon, which would appear to indicate that Lester is still considering returning to the team where he played a key role in World Series championships in 2007 and 2013.

In fact, Bradford reported, ownership groups for all four teams vying for the services of Jon Lester have become directly involved in the talks — and that’s the reason why progress toward the pitcher’s final decision has slowed down.