Boston Red Sox owner John Henry did something admirable earlier last month, acknowledging the mistake he made as Jon Lester moved closer to free agency in 2015. If you recall, Boston lowballed Lester on an initial offer, $70 million, for less than half of what the left-hander eventually got from the Chicago Cubs, $155 million.
The Red Sox lost an ace with a strong postseason history in the prime of his career, without proposing anything close to market value. By doing that, they turned the offseason negotiation into a competition they were destined to lose. "I think we blew the signing [of Jon Lester] in spring training," Henry said last month.
Hey, live and learn, right?
But somebody has to say it: Henry and the Red Sox have made another mistake with a lefty ace, Chris Sale, this time with an outsized $145 million, five-year extension on top of the $14.5 million he will make this year. In the current context, in the current market, it appears to be a significant overpay and an assumption of enormous risk.
The past few years have been filled with a predominance of team-friendly, risk-free deals, and this is a great contract for Sale. One official not involved in the talks said of Sale's agent, B.B. Abbott: "He did a great job." It's good to see one of the best and most competitive pitchers of his generation get significant compensation. He has worked and prepared diligently, performed brilliantly, and now he is rewarded. No pitcher in baseball history has struck out more batters per nine innings, and only 10 pitchers, ever, have a better adjusted ERA+ than Sale's 144.
When he joined the Red Sox, Sale talked about how he wanted to win, and backed up his words with his actions at the end of last season. His fastball velocity dropped significantly in the last month, from 97.6 mph on Aug. 12 to 90.2 mph on Sept. 26, and yet he kept taking the ball through October, giving new manager Alex Cora and his teammates all he had.
Even after all that, Sale still made himself available to pitch in the World Series, starting Game 1 and contributing four innings, before entering in relief in the bottom of the ninth of Game 5. Riding the adrenaline of the moment -- driving the adrenaline, really -- Sale threw hard, he spun the ball well and Manny Machado swung over the top of one of his sliders to end the World Series.
It's good that it ended there, said one person with knowledge of the Red Sox's pitching quandaries, because that would have been it for Sale in the World Series. Like David Price, like Nathan Eovaldi, like all members of the Red Sox staff, Sale gave everything he had to give, the marathoner sprinting to the finish line. Because of that selflessness, Henry will get his fourth championship ring as the principal owner of the Red Sox.
But there is a practical side to Henry as well, someone who gets the numbers, and the numbers at the end of last season lead to natural questions about whether Sale's stuff will hold up through even the first years of the deal. Roy Halladay was the best pitcher in baseball in 2010, and less than three years later, in 2013, he was done, his ERA close to 7. Clayton Kershaw is arguably the best regular-season pitcher in history, and now his average fastball velocity drops below 90 mph some days -- and for the fourth straight year, he's dealing with some physical issues. It's not a question of if there will be a breakdown with Sale, but when; that's the way it is with all pitchers. Anybody who watched him pitch last October could see the red flags.
This is why there was more than a little shock in the industry that the Red Sox committed big dollars to Sale through the 2024 season. He got more money than any free-agent starter since Price. "If you're going to pay him like an elite free agent," asked one official, "why not wait until the year's out, so you can gather some more information about where he is physically?"
Or, some rival officials thought, offer him fewer years. A lucrative three-year extension might've been slightly more sane. But a six-year commitment? That was a surprise to other teams.
The Red Sox have said since January that Sale was given a clean bill of health by their doctors and resumed his throwing program on time. They're comfortable with what they're hearing, and maybe they thought if Sale reached the open market next fall as the best available left-hander, some other team with lots of dollars available (Yankees? Phillies?) might have made a hard run. If they hadn't reached an extension this spring, maybe it would've turned into a competition -- as it did with Lester, the regret that apparently gnaws at Henry.
Last year, Kershaw had a 2.73 ERA with 155 strikeouts and just 29 walks, and with a newly negotiated extension, he's signed through 2021, for $93 million. Patrick Corbin was the highest-paid free agent, made all of his starts last year, is slightly younger than Sale -- and he got less money, $140 million over six years. Justin Verlander is six years older than Sale, but made 67 regular-season starts the past two years, racking up 420 innings, and he got $66 million over two years.
There's no getting around the fact that Sale's deal doesn't really slot into the other payouts in the market, and is probably greater than what other teams would be willing to pay, seven months before he's actually on the open market.
It's Henry's money, to spend as he sees fit, and maybe he views it as some kind of a Lester penance. He wasn't going to let this lefty ace get away.