BOSTON -- Determined not to repeat the mistake they made with Jon Lester five years ago, Red Sox ownership on Monday voiced a priority to sign ace lefty Chris Sale to a long-term extension.
In Spring Training of 2014, Lester was entering his "walk year" and the Red Sox were fresh off a World Series championship. Lester had stated he would take a hometown discount, but Boston got negotiations off to a bad start with a four-year, $70-million offer that was nowhere close to market value.
So, here Sale is this spring, entering his walk year as the Red Sox are again coming off a World Series championship.
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Though Red Sox principal owner John Henry once said that signing pitchers in their 30s to long-term contracts didn't represent good business, he clearly thinks Sale -- who turns 30 next month -- is an exception.
"I think Chris falls out of the norm because he's just such a great [pitcher]," Henry said. "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 in the World Series. So he's a special player. We would love to be able to sign him. I think he would like to as well."
Henry and Red Sox chairman Tom Werner confirmed that the club has had discussions with Sale and star shortstop Xander Bogaerts, who is also eligible for free agency at the end of the season.
Though the owners want to keep negotiations private, Henry indicated the possibility of signing Sale before he reaches free agency. While some players are determined to test the market, Henry doesn't think that's the case with Sale.

"But there are the realities of the marketplace and budgets, and this is his opportunity to be a free agent, potentially, which we'd like to avoid, but I think he would as well," Henry said. "So something could happen."
That would certainly be great news for the Red Sox, who have had to watch Lester pitch well for the Cubs for the past four seasons, all the while knowing he never wanted to leave Boston.
"I think we blew the Jon Lester [negotiations]," Henry said. "We blew signing him in Spring Training. For reasons that are pretty apparent now, which I won't go into, but they're apparent."
Though Sale experienced left shoulder inflammation in the second half last season, Boston doesn't have long-term health concerns about him at this time.

"He's healthy. He had minor issues," Henry said. "They were able to take their time and give him some rest at one point, but he hasn't had any significant shoulder issues."
"It would be great," manager Alex Cora said when asked about the possibility of Sale signing an extension. "He's what you want from players. You talk to him, the interviews and how he handles everything, he handles Boston, he loves it. Very humble guy. It would be great."
While the 2019 Red Sox have a stacked cast that has as good a chance as any team to win the World Series, there are many decisions to make about the core in the upcoming years.
Aside from Sale and Bogaerts, Rick Porcello is also eligible for free agency at the end of the 2019 season. Mookie Betts and Jackie Bradley Jr. are under the club's control through '20. J.D. Martinez has opt-outs after each of the next two seasons.
The Red Sox are doing what they can to keep as much of the core intact as possible.

"Bogaerts is an extraordinarily great player. Sale, Mookie Betts, we'd love to be able to have long-term contracts with all of them," Werner said. "But our conversations with them, which are ongoing, are private. I think that's the best way to consummate a deal if one can be made."
Reality is that the Red Sox will lose some of their star players in the coming years.
"It's really hard to keep 25 players every year together. We'll do everything we can to keep this team together, and continue to rebuild and replenish. But free agency is what it is," Henry said. "We have a lot of young players who will mature at the same time, mature for free agency. We won't be able to keep all of them. We may have the largest payroll in baseball, but even then, you can't keep all of your players the way free agency works these days."