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The Red Sox Just Invested in Chris Sale. What Does That Mean for Boston's Young Core and MLB?

Jon Tayler
The Red Sox Just Invested in Chris Sale. What Does That Mean for Boston's Young Core and MLB?

His name may be Chris Sale, but Boston just paid full price for him. (Sorry.) On Friday afternoon, news broke that the Red Sox and Sale agreed on a contract extension with their ace lefty, with ESPN’s Jeff Passan reporting terms of five years and $150 million, keeping him off the 2020 free-agent market. It’s a hefty chunk of change for one of baseball’s best starters, but what does it mean for both Boston and the league as a whole? Here are four thoughts on the dominoes knocked down by Sale’s decision.

1. No sale on Sale

With this new deal, Sale vaults into the upper echelon of salary for players. His total contract isn’t what is notable—$150 million doesn’t get him inside the 20 biggest active deals, or even No. 1 in his own rotation (that honor belongs to David Price and his $217 million pact)—but by average annual value, he’s now elite. At $30 million per year, he’s now tied with Max Scherzer for the eighth highest AAV ever in major league history; among starters, he trails only Zack Greinke ($34.4 million), Price ($31 million) and Clayton Kershaw ($30.7 million).

That’s quite the company to keep, and given how good Sale has been, it makes sense. A seven-time All-Star and owner of the highest strikeout-per-nine rate in baseball history, Sale is one of the best power pitchers ever to take a mound. Since joining Boston via a blockbuster trade after the 2016 season, he’s posted a 2.56 ERA and 545 strikeouts in 372 1/3 innings. Since becoming a full-time starter in 2012, his 143 ERA+ is second only to Kershaw among all pitchers in that span with 1,000 or more innings thrown. The spindly southpaw is a perennial Cy Young favorite (though always a bridesmaid; he’s finished in the top five of the voting the last six years and was runner-up in 2017, but never won it) and the undisputed ace of Boston’s staff. He even recorded the final out of last season’s World Series, clinching the franchise’s fourth title since 2004.

All of these are good reasons to pay Sale. What makes this outlay surprising, though, is his age and durability. On the former front, Sale turns 30 in one week, and the history of pitchers holding up past that round number isn’t a great one. In terms of the latter, he’s coming off a season in which he made just 27 starts and threw only 158 innings—just 17 of those coming between the end of July and the start of the postseason—due to shoulder troubles. A healthy Sale is one of the most dominant forces alive, but given his Gumby-on-a-diet body and a pitching motion that looks like wind chimes being tossed about in a hurricane, it’s anyone’s guess as to how long that’ll be the case.

Still, you make exceptions for great pitchers, and that’s Sale. Nor did the Red Sox have much of a choice here: The rotation aside from him is Price, the acceptable Rick Porcello, talented yet inconsistent lefty Eduardo Rodriguez, and hard-throwing yet oft-injured righty Nate Eovaldi. With both precious little internal depth to replace Sale and a free-agent class quickly losing all its stars (more on that later), president of baseball operations Dave Dombrowski’s hands were tied. That’s going to have consequences for the rest of Boston’s future. Speaking of which…

2. Who’s the odd man out in Boston?

With Sale locked down, the question now is what happens with the rest of Boston’s core. His new contract likely won’t be made official until after Opening Day for luxury tax reasons, and that’s important for Boston, which has the biggest payroll in baseball ($222 million) and is one of just three squads currently over the tax threshold. Ordinarily, that results in a pretty minor penalty, but as a repeat offender several years running, the Red Sox will be paying 50% on every dollar over the $206 million limit for this season.

That will almost certainly extend into 2020 and beyond, as the cap is barely budging up to $208 million. Boston is already on the hook for $109 million in guaranteed salary next year before Sale is factored into the equation. Add in a dozen arbitration-eligible players, and you’re creeping toward $200 million before making a single addition or retaining any key free agents.

That last part is crucial, as Sale wasn’t the only big name the Red Sox were set to lose next winter. The potential butcher’s bill also includes shortstop Xander Bogaerts, Porcello, and possibly All-Star slugger J.D. Martinez, who can opt out at the end of the season. In Martinez’s case, that would mean foregoing the three years and $62 million still left on his contract after 2019, but given his brilliant ‘18 campaign and whatever he does this season, he could stand to make more if he tries free agency again. (Albeit at age 32 and as a bad defensive outfielder.)

How the Red Sox triage that trio is complicated. It’s hard to see ownership digging up the money for yet another nine-figure extension—almost certainly what it would cost to keep Bogaerts—after a winter in which they retrenched significantly. Boston’s bullpen is so thin that Jenrry Mejia—who’s been suspended three times, had a permanent ban reversed and hasn’t pitched in the majors since 2015—has a decent chance to make the Opening Day roster, and yet the front office still wouldn’t pay to bring back All-Star closer Craig Kimbrel. Dombrowski and company may simply elect to let Bogaerts, Porcello and Martinez test the waters. If nothing else, Sale’s extension showed that he was the pending free agent most important to the front office, with principal owner John Henry pointedly refusing to make the same mistakes that cost the team former lefty ace Jon Lester.

But all of those conundrums pale in comparison to the biggest decision the Red Sox face: What to do with Mookie Betts. The defending AL MVP is under contract for 2019 and ’20, but the latter is his final year of arbitration before free agency beckons. And if you think Sale cost a fortune, than Betts—especially fresh off the mammoth sums given to Manny Machado, Bryce Harper, Nolan Arenado and Mike Trout—is going to command the GDP of a small Asian nation. Boston’s front office hasn’t made any progress in locking up Betts long-term: He rejected an eight-year, $200 million deal from the team after the 2017 season, and he’s only gotten more expensive since then. “I don’t expect anything to happen until I’m a free agent,” he told reporters after Trout’s mega-deal was announced. “I’m under no pressure to do anything.”

He may not be, but the Red Sox certainly are: Letting Betts walk would be a catastrophe. But in order to be the best, you have to employ the best, and that means paying them like the best. It’s going to be an expensive challenge for Boston to keep this championship band together, but with the equally powerful Yankees and Astros looking to dethrone them, ownership may have no choice but to spend like no team ever has before.

3. Who else is going to get paid?

Sale’s contract will have a ripple effect outside of Boston, too—about 200 miles south, to be precise, where the Mets remain in a stalemate with their ace, Jacob deGrom. The 2018 NL Cy Young winner is in Sale’s class as one of the league’s best pitchers, and he has just two seasons left before he’ll reach free agency. For any other team, that would mean a new deal already in place. But given that this is the Mets we’re talking about, talks have dragged on through the winter, with a deGrom-imposed deadline of Opening Day rapidly approaching. According to SNY’s Andy Martino, the righty is looking for a deal exactly the size of Sale’s—five years, $150 million—but the team apparently has yet to make him a formal offer. Sale’s extension probably isn’t going to make these talks any easier.

Regardless, deGrom isn’t the only pitcher who’ll be looking for a bigger payday after Sale’s score. Astros righty Gerrit Cole is set to hit free agency this winter and is coming off one of the best seasons of his career; so is rotation-mate Justin Verlander. The Mets also have Zack Wheeler, who’ll be a free agent after the season as well, to worry about. Looking ahead a year, you have Trevor Bauer—already adamant he’ll go year to year for the rest of his career—reaching the open market, as well as James Paxton, Robbie Ray, and Masahiro Tanaka. It’s unlikely most of those pitchers will get new contracts, but their agents will probably all be monitoring their phones regardless.

4. Whither free agency?

As noted, Sale’s extension takes him out of next offseason’s free-agent class—one that, even before he was knocked out, has thinned. The recent spate of new contracts this spring has removed the two best hitters who were going to hit the market in Arenado and Paul Goldschmidt, as well as Miles Mikolas and Aaron Hicks. The 2020 class, meanwhile, has lost Trout and Carlos Carrasco. There are still big names available—next winter brings us Bogaerts, Cole, Verlander, Madison Bumgarner, Anthony Rendon, Yasiel Puig, and Khris Davis, among others—but seemingly fewer and fewer players are making it to free agency.

Given the financial state of the game and the fear of a work stoppage when the current collective bargaining agreement expires after the 2021 season, it’s unsurprising that a number of players are choosing to get paid now. Even the elite ones like Sale, Trout and Arenado are passing on the opportunity for almost certainly more money than even these huge contracts will pay them.

The effect of all this is multifold. First, it drastically limits how much teams can improve themselves every offseason, which increases the stratification of the league. Second, it leaves only mid-tier players available in free agency, and those are the players that teams are already least willing to spend to get. Third, these new extensions will be the comps going forward for just about everyone, and since extensions are by and large team-friendly agreements, the ceiling of how much a player can earn is being lowered, which further hurts free agents.

As I wrote yesterday with regards to Blake Snell’s extension, owners have long sought to destroy or rein in free agency. It turns out that the best way to do it was create a system in which players are squeezed financially from day one of their careers, and then simply pick them off with extensions, making sure they never reach the open market in their primes. That won’t hurt guys like Trout or Arenado or Sale, but it crushes the non-elite options. Nor does it make for a particularly fun or interesting offseason for the fans. The hot stove used to sizzle on the regular over the winter, but it’s gone ice cold the last two years. That can only hurt the game, even if the owners are reaping the financial rewards.