As the saying goes, one person's loss is another person's gain. For the Cubs, this is especially true when it came to signing Jon Lester.
Lester entered spring training in 2014 on the last year of his contract with the Boston Red Sox. According to NBC Sports Boston's Justin Leger, the Red Sox reportedly offered Lester a four-year extension worth $70 million before the season started.
As the story goes, the two sides did not agree to a new deal and the Red Sox traded Lester to the Oakland Athletics ahead of the 2014 trade deadline. Lester went on to sign a six-year, $155 million deal (with a vesting option for 2021) with the Cubs ahead of the 2015 season.
At a press conference on Monday, Red Sox owner John Henry admitted the team mishandled negotiations with Lester.
“I think we blew the Jon Lester — we blew the signing in spring training,” Henry said. “And for reasons that are pretty apparent now, which I won’t go into, but they’re apparent. But it wasn’t… you can see what’s gone on in free agency.
"The price of WAR has gone up radically that it’s difficult, whether it’s a pitcher or a position player, entering into a really long term contract with high dollars.”
The Red Sox are in a similar position now with former-White Sox starter Chris Sale, who will hit free agency after the 2019 season. Henry was asked if his philosophy has evolved regarding signing pitchers 30 years old or above.
“I think Chris [Sale] falls out of the norm because he’s just such a great — not just a great pitcher but a great part of the team as we saw in the World Series he had quite an impact just being on the bench during the World Series,” he said. “So he’s a special player.
“We would love to be able to sign him. I think he would like to as well. But there are the realities of the marketplace in budgets and this is his opportunity to be a free agent, so, potentially…something could happen.”Click here to download the new MyTeams App by NBC Sports! Receive comprehensive coverage of your teams and stream the Cubs easily on your device.