Red Sox rumors: Boston trying to extend Jon Lester

The Boston Red Sox have recently picked up extension negotiations with left-hander Jon Lester in what could be their final attempt to extend him before the end of the season, according to Buster Olney of ESPN.com. Rob Bradford of WEEI.com writes that no significant progress has been made between the two sides, but that the Sox are hopeful of getting talks underway with Lester once again.

Lester, who is 9-7 with a 2.92 ERA in 17 starts on the season, will join Max Scherzer and James Shields as the most coveted starting pitchers on the free agent market this winter. The Red Sox have long-expressed their desire to keep the southpaw in Boston on a long-term basis, but have been unable to make significant progress on a deal and now have only four months before Lester hits the open market.

As Jeff Passan of Yahoo! Sports reported in mid-April, the Red Sox initially offered Lester an extension worth $70M over four years, which was significantly lower than his asking price. The 30-year old is expected to command a much larger deal than that of Reds' righty Homer Bailey, who signed a six-year, $105M deal before the season to avoid free agency this winter.

Boston will likely have to go into the six- or seven-year range to extend Lester, who has established himself as one of the best left-handers in the game since breaking into the bigs in 2006. The team could trade starters Jake Peavy or Felix Doubront before the trade deadline in order to make room in the rotation for youngsters Rubby De La Rosa and Brandon Workman, but have made it clear that they want to make a long-term commitment to Lester as the ace of their staff.