Let’s just say that we are far removed from the times when Jon Lester and the Boston Red Sox were talking about a team-friendly, hometown discount in a contract extension.
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It might be that when Lester discussed a potential hometown discount, he did not necessarily mean in terms of years. Big league players often look for an extra year or two if the deal being negotiated is considered their last big chance to cash in for big money.
When the Red Sox offered Lester four years for $70 million, they were promptly rejected by their ace lefty. Extension talks between the two are supposedly ongoing but certainly do not seem to have much traction at this point.
The possibility of Lester hitting the free agent market becomes more real by the day, especially given the player’s own preference not to get deep into negotiations during the season.
Nick Cafardo of the Boston Globe writes that if Lester reaches free agency, he is not likely to re-sign with the Red Sox. He would be more likely to sign with a different team, a team willing to offer six or seven years in a blockbuster deal.
Cafardo notes that the Red Sox are reluctant to tie themselves down with long-term deals for veterans due to past mistakes:
"There’s no easy solution. It seems once the talks get to free agency, Lester will be lost, because the length of contracts being offered won’t be compatible with what the Sox are trying to do.That will not be a popular outcome."
Lester has been nothing short of outstanding this season and is among the fan favorites in Boston. If he does reach free agency, the Red Sox front office will hope that their fans buy into the business of baseball and understand the logic behind their decision.