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Alex Speier

For Chris Sale, money isn’t everything when it comes to contract negotiations

Chris Sale (right) is entering his 10th MLB season. Barry Chin/Globe Staff/Globe Staff

FORT MYERS, Fla. — What does Chris Sale value?

At a time when the Red Sox lefthander is entering the final season before he’s eligible for free agency, that question looms large. If his mission is to extract every possible dollar, to erase old earnings landmarks and establish new ones, then common ground with the Red Sox on an extension before hitting the open market would seem remote.

But if his checklist of priorities features money as merely one of several factors, then it’s not hard to see how he and the Red Sox might find a way to extend his stay in Boston beyond 2019.


“I think we’re both mutually invested in this,” Sale reiterated Tuesday. “We’ve both said on both sides that it’s a possibility, for sure.”

Sale’s world view on the business of baseball was framed during his junior year at Florida Gulf Coast University, when his first son Rylan was born on May 4, 2010, just weeks before the draft. At the time, prominent first-rounders such as Sale (taken No. 13 overall by the White Sox) often went through a summer-long game of negotiating chicken in order to maximize their bonuses.

That year, Drew Pomeranz ($2.65 million) and Matt Harvey ($2.5 million) — pitchers taken a few picks in front of Sale — as well as Anthony Ranaudo ($2.55 million from the Red Sox after being the No. 39 pick) got bonuses well above the slot recommendations. Sale, with wife Brianne and one-month-old Rylan to support, wasn’t going to wait.

He signed less than two weeks after the draft for the slot recommendation of $1.565 million — albeit with an assurance by the White Sox that he would be considered for a callup (and, thus, a big league salary) within weeks. For Sale, security and a bird in hand meant more than the chance to test the limits of his earnings potential.


“I was offered the deal of a lifetime, obviously, but I wasn’t waiting around,” said Sale. “I was ready to go. Basically, from the time [Rylan] was born until the last game of the year in 2010, I was just completely numb. I was young. I didn’t know anything about professional baseball. I was naive to basically everything about it, just trying to survive.

“I didn’t know what I was doing. I just knew that I could pitch, they wanted me to pitch. I guess that’s kind of my foundation of my entire philosophy: hand me the ball and I’m just going to throw it until you take it out of my hand.

“That’s kind of where I was. I didn’t want to be heard or seen in the clubhouse, just kind of sneak in, sneak out, get my work done, pitch good, and stay out of everyone’s way. That definitely helped me get to where I am now.”

Family security again played a role in how Sale approached the idea of a long-term deal early in his career. Prior to the 2013 season, the lefthander — who had spent just over two years in the big leagues, including a 2012 season in which he emerged as an All-Star starter — again prioritized security over earnings potential.

He agreed to a five-year, $32.5 million deal with the White Sox that included a pair of team options, forgoing up to three seasons that would have been incredibly lucrative on the open market. Indeed, the value of those three seasons was so high that the Sox deemed them worth the four-player package (Yoan Moncada, Michael Kopech, Luis Alexander Basabe, and Victor Diaz) they sent to the White Sox for Sale in December 2016.


Had Sale not signed that deal and instead been a free agent in 2016 coming off his age-27 season, he might have been in line for a contract that surpassed the gold standards for total value ($217 million for David Price) and average annual value ($34.4 million for Zack Greinke). Instead, by the end of this year, he’ll have made a bit more than $39 million over his three years in Boston — a bit more, perhaps, than he’d have made in one year as a free agent.

Yet Sale has no regrets.

“Would I do it again? I wouldn’t flinch,” he said. “Knowing what I know now, going back to that moment in time, I would have done the same thing. Especially with the numbers that were in front of me, I thought I would have been an idiot to not do it.

“If I didn’t have kids, wasn’t married, I probably wouldn’t have signed that deal. But I was 23 years old. I’ve got a 2-year-old at the house, been married two years at that point. Put $30 million in front of me, I’m taking it.

“I get to play professional baseball, major league baseball, for five more years and make really good money doing it at 23. I just wasn’t going to have to worry about any of that [stuff] and my family was going to be taken care of, my kids were going to be able to go to college.


“That was basically the only thing on my mind, being able to take care of my family. That’s my responsibility.”

Sale understood that there was fragility to success. As much as he believes in his abilities, he isn’t a traditional elite pitcher who has enjoyed such a perch for his entire life. Out of high school and even through his freshman year of college prior to a massive delivery overhaul, Sale was a pitcher who worked in the mid-80s, a 21st-round choice in the 2007 draft who was repeatedly overlooked.

Sale also appreciated that the deal (if the options were exercised) would bring him to nine years and 61 days of service time, the cusp of a full big league pension. He also believed that the White Sox had promise, and he liked the idea of being part of a group that he expected to grow and win together. Moreover, he appreciated that he didn’t have to worry about the financial implications of his work on the mound.

“I just didn’t have to worry about the b.s. of baseball, the business,” said Sale. “I’m not a business guy. I’m a baseball player. Let’s take care of all this [stuff] and let me go play.”


Once he joined the Red Sox, he had the added value of spring training in Fort Myers — an easy commute from his home in Southwest Florida, and not too far from Lakeland, where he grew up.

And, of course, the Red Sox have already given him a chance to experience a championship — and with a group of starters with whom, in age and attitude, he feels incredibly close.

“I just got goose bumps thinking about it,” Sale said at the mention of getting a ring in April. “I still have a burning desire to win. It never stops. It’s an unbelievably horrible characteristic to have, but I’m not satisfied.”

There’s no guarantee Sale will work out an extension with the Sox, particularly given that he now does have the financial security he sought with his first deal. There’s a chance that he could place greater emphasis this time on maximizing his earnings, a matter of growing concern among players.

“We have a couple different scenarios,” Sale said of talks with the Sox. “If it works, awesome. If not, I’m still doing the same things. I’ve got a job to do, and that’s all I’m focused on. If it happens, great. If not, great.

“Obviously, this go-round is a little different than the last one with the contract situation. The wheels could fall off tomorrow and I can just take it to the house. There’s no worst-case scenario for me, knock on wood.

“I’m doing what I love to do. I can’t really complain past, present, or future.

“But just because I’m in a different area of my life doesn’t mean I have to change my values or my focus. What I’ve done my entire career has been just baseball — play baseball. That’s it.

“I’ve been stuck in that way for so long that I have a really hard time thinking I’ll have to find a way out of it.”

Alex Speier can be reached at Follow him on twitter at @alexspeier.