Chris Sale gets a five-year extension from Red Sox

FORT MYERS, Fla. — Early in spring training, Red Sox principal owner John Henry looked back with some chagrin on his team’s efforts to extend lefthander Jon Lester in spring training five years earlier.

“We blew that signing in spring training,” Henry, the Globe’s owner, said in February.

The team didn’t want to do the same with Chris Sale. According to multiple major league sources, the Red Sox and Sale have agreed to a five-year, $145 million extension that will run from 2020-24. The contract includes an opt-out for the pitcher after 2022 and deferrals that will lower the average annual value of the deal between 2020 and 2024. Sale, according to a major league source, passed his physical on Friday night.

The deferrals lower the payroll impact of the deal as calculated for luxury tax purposes to $25.6 million per year — something that was important to both Sale and the team to permit the Red Sox the greatest possible flexibility to build the rest of their roster.

There are escalators that can increase Sale’s salary by up to $2 million per year starting in 2021 based on how Sale finishes in Cy Young voting in the previous year.

The deal includes a $20 million team option for 2025 that becomes guaranteed if Sale finishes in the top-10 in Cy Young voting in 2024.

There are escalators that could increase the value of the option as high as $25 million based on how Sale finishes in Cy Young voting in 2023 and 2024.

When Sale reaches 10 years of big league service time in 2020, the Red Sox will give him the rights of a 10/5 player (10 years in the big leagues, five with one team), allowing him to veto any prospective deal.

The deal assures that Sale — who would have been eligible for free agency after this year — will instead continue to anchor the Red Sox rotation, and, the team hopes, its October ambitions, for years to come.

“It improves our chances of winning as opposed to not having Chris Sale,” said David Price. “I’m sure our hitters don’t want to face him and I don’t want to not root for him.”

In two seasons in Boston, Sale has been the most dominant starting pitcher in baseball when on the mound. In 59 starts, he’s 29-12 with a 2.56 ERA, 13.2 strikeouts per nine innings, and 1.9 walks per nine innings. He’s been the American League’s starting pitcher in the All-Star Game in both seasons.

Red Sox pitching coach Dana LeVangie spoke glowingly of the lefthander’s abilities and personality, describing Sale as “a kid that didn’t grow up in Boston but he sure acts like he did.” LeVangie said that Sale’s deception and ability to manipulate the ball will allow him to remain a standout pitcher for years to come, even if he becomes less of a pure power pitcher at some point in his career.

“He’ll be a force throughout his career,” said LeVangie. “It’s very similar to watching Pedro [Martinez]. You don’t ever want to miss a pitch that he throws. You’re always expecting something special when he’s on the mound. I think the atmosphere that these guys carry with them is so unique and special . . . These guys don’t come by too often, and when they do, you hope you have them for a long time.”

Still, Sale’s conclusion to 2018 — in which he went 12-4 with a 2.11 ERA, 13.5 strikeouts per nine innings, and a microscopic 0.86 WHIP – raised some concerns about his long-term health. After Sale delivered an American League-high 214⅓ innings in 2017, he logged just 158 innings in 2018 while spending time on the DL in August and September for what the Red Sox called shoulder tendinitis.

But despite Sale’s limited workload down the stretch last year and his uneven performance during the postseason, the Red Sox and Sale have all suggested that the lefthander is healthy as he prepares for his second straight Opening Day start as a member of the Red Sox. Henry said earlier this spring that Sale “hasn’t had any significant shoulder issues.”

The lefthander has had a smooth buildup to the season in spring training. By design, the Red Sox held him and several other rotation members back this spring to control their workloads after last year’s title run. Sale made his first and only Grapefruit League start on March 16, tossing four shutout innings and striking out seven while walking none and showing excellent command. Though he was scheduled to start Friday’s Red Sox game against the Twins, he was a healthy scratch from the contest while awaiting results of the physical.

The extension will be appended to Sale’s prior deal. Under the terms of the second option year of the deal he signed with the White Sox in 2013, the lefthander was scheduled to make $15 million in 2019. He will still do so.

On top of that, the extension will pay Sale $30 million in 2020, 2021, and 2022 (after which he has the right to opt out) and $27.5 million in 2023 and 2024.

With that contract structure, the Red Sox’ 2019 payroll will remain unchanged; the team still projects to remain below the third and highest penalty tier at which a 75 percent penalty takes effect for spending beyond $246 million.

Sale was entering the second and final option season of a five-year, $32.5 million deal he signed with the White Sox in March 2013. Given that he’s finished in the top five of AL Cy Young voting in each of the first six years of that deal, the lefthander has been one of the foremost bargains in the game. Yet he had no regrets about the decision to prioritize security for his family over maximizing his earnings.

“Would I do it again? I wouldn’t flinch,” Sale said earlier this spring.

In a sense, with the extension, he proved the point. With a healthy 2019 season, Sale could have surpassed the seven-year, $217 million standard that teammate David Price set for the largest guaranteed deal ever given to a pitcher, and he likewise might have challenged Zack Greinke’s $34.4 million record for the largest average annual value (AAV) for a pitcher.

Instead, his extension of $29 million per year will rank as the sixth-largest AAV ever for a pitcher, behind Greinke, Price, two Clayton Kershaw deals with the Dodgers, and Max Scherzer. Yet all of those pitchers reached free agency (Kershaw signed his first with the Dodgers while under team control, but then renegotiated the deal as a free agent this winter). Sale, who has made no secret of his enjoyment of his Red Sox experience, didn’t relish a foray into the open market for its own sake.

Sale would give the Red Sox four starters who are under team control for years to come, joining Nathan Eovaldi (signed through 2022), Price (2022), and Eduardo Rodriguez (not eligible for free agency until after 2021). His deal will take effect after the 2019 season, when Rick Porcello’s deal (a $20.625 million AAV) comes off the books. (Porcello has said on multiple occasions this spring that he’d like to re-sign with the Sox as well.)

By re-signing with the Sox, Sale, who turns 30 on March 30, will continue to live at home during spring training (he resides in southwest Florida), to pitch in a passionate baseball city, and to continue pursuing championships — something for which the lefthander said he had an even greater appetite after 2018.

“I still have a burning desire to win,” he said.

That same desire is what led the Red Sox to acquire Sale in the first place. After 2016, the team made a bold bet in landing Sale from the White Sox in exchange for a four-prospect package headlined by potentially elite young talents in Yoan Moncada and Michael Kopech. At the time, the calculus was clear: Sale could improve the team’s chances of winning a championship (or championships) so much over his three remaining seasons of team control that he was worth whatever future impact the minor leaguers might one day be capable of delivering.

The 2018 World Series — punctuated by Sale striking out the side in Dodger Stadium — allowed the Sox to make good on that bet. Now, the Red Sox are willing to make another.

2019 Baseball Preview coverage:

■ ‘They’re special kids’: The last great Red Sox outfield on the new great Red Sox outfield

■ How the Red Sox outfielders play their positions at Fenway

■ Chad Finn: An appreciation of the Red Sox’ dynamic outfielders

■ Profiles of Mookie Betts, Jackie Bradley Jr., and Andrew Benintendi

■ Sean McDonough is back where he belongs — calling Red Sox games

■ Tara Sullivan: These Red Sox deserve to be confident as they try to repeat. But they should also be wary

■ Globe staff predictions for the season

Alex Speier can be reached at alex.speier@globe.com. Follow him on twitter at @alexspeier.