When John Henry sat on the bench outside JetBlue Park in late February 2019 and finally admitted the Red Sox had botched the Jon Lester negotiations from five years before and weren't planning on repeating their mistake, one person took particular notice.
That would have been Chris Sale.
"Oh, absolutely," Sale told WEEI.com when asked if that message from the Red Sox principal owner caught his attention.
When Sale was informed that most of the media believed that once Henry uttered those words the then-Red Sox ace was bound to get a contract extension done, the pitcher laughed and said, "I knew they were going to sign me, too."
Then Sale added this anecdote: "We went to Chicago later that year and we were working out in the weight room over at their place and I was kind of waiting to see him in the weight room or in passing or whatever but I didn’t. I was like, ‘Whoever sees Lester first, tell him I said, ‘Thank you.’"
Sale - who would have been eligible for free agency after the 2019 season - ultimately signed a five-year, $145 million extension, which was announced on March 23. It was the culmination of a month of negotiating, that the pitcher always believed was going to end in one place - a commitment to remain with the Red Sox.
"Yes and no," Sale said when asked if the weeks leading up to the agreement were chaotic. "It was chaotic in the sense that it was just mind-blowing. I was excited. It was very, I’m not going to say easy, but it was very fluid.
"Their first offer was the first week or so of spring training and everything was very upfront. Everything was on the table. There were no secrets. There were no mystery doors. It was very easy and at the very end of it I went and talked to Dave (Dombrowski).
"I told them, I have played baseball … I understand the business side of it, I just don’t like it. I’m a ballplayer. That’s what I have done my entire life. When I was 4 years old I didn’t talk about how rich I wanted to be. I talked about how much I wanted to be a ballplayer. That has always been first and foremost. So I told them I don’t want this getting in the way of my actual business of taking care of what I need to take care of, and that’s pitching. I told them,’If we don’t get something done in spring training we’ll figure it out at the end of the year.’"
It is all the same sort of conversation and drama that these current Red Sox are navigating their way through, with foundational players such as Xander Bogaerts, J.D. Martinez, Nathan Eovaldi, Kiké Hernandez, and Christian Vazquez all eligible for free agency after the 2022 season. Then, of course, there is the conversation involving Rafael Devers, who can hit the market after 2023.
The consistent theme with most of these situations involves the players usually not wanting to drag any negotiations into the regular season, as was the case with Sale three years ago.
"You have a lot of stuff going on in the season, anyway," Sale said. "Having, the quote-unquote pressure - although I have never had it because I have never been a free agent - lasting throughout the year. I can only imagine what it would feel like being in June hitting .215 after turning down a whatever extension. Then you start pressing and things like that. Some guys do it and they get through it, I guess.
"It gets talked about, it’s just not at the forefront and that might be hard to understand because it’s a lot of money. It’s a lot. These are big numbers. But my experience and what I’ve seen, we’re just so wired to do what we’re supposed to do … Yeah, you might talk about it in passing at breakfast, but it’s not, ‘Hey, today is this,’ or ‘Hey, today is that.’'
With one day left until Opening Day, contractural "this" or "that" won't be part of the conversations for much longer. Three years ago, the Red Sox were able to avoid it with Sale (and Bogaerts, a few days later). This time? We'll see.
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