It wasn't much of a surprise that Red Sox chairman Tom Werner made it known last week the team had begun to engage Chris Sale's representatives about a contract extension.
Sale is easily the biggest name on the Red Sox' list of potential free agents, and while the case could be made that Xander Bogaerts will be every bit as difficult to replace should he sign elsewhere, Sale that rarest of baseball species: the proven No. 1 starter.
Such pitchers are hard to find. If you're being generous, there might be a half-dozen or so around the game. Add in that the Sox mortgaged their two best prospects (Michael Kopech and Yoan Moncada) to get him from the White Sox and the desire to retain him is even greater.
His habit of faltering physically in the closing months of each season is something of a red flag, yes. But other than last summer, when mild shoulder inflammation limited Sale's workload (17 innings after July 27) and effectiveness (diminished velocity), Sale has been a workhorse, reaching 200 innings and 30 starts in each of the prior five seasons.
The Sox' well-documented aversion to 30-something starters has to be taken into account here, as well. But if Sale leaves, the Sox will be without an obvious No. 1 to take his place, and with no such prospects in the system -- at least for the next few years -- they'll have to either trade precious prospect capital (again), or pay dearly for someone like him on the free agent market.
And given that the Sox already know that Sale can handle the Boston experience -- something that can't necessarily be said of others -- there's incentive to get a deal done soon.
If there's a positive to the onset of negotiations, it's this: Sale, by all accounts, would prefer to stay with the Red Sox. He's enjoyed his first two seasons, loves the passion that's on display almost nightly at Fenway, likes his teammates, the training staff and both manager Alex Cora and pitching coach Dana LeVangie.
These are considerable advantages for the Red Sox. They don't have to try convincing him that his time will get better, or have to overpay to retain him.
But, of course, Sale isn't about to undersell his own value. He's a dominant, durable starter and will expect to be rewarded commensurately. If he goes onto the market, he'll be joined by some other impressive starters (Gerrit Cole, Justin Verlander, and Madison Bumgarner, to cite the top three), but Cole doesn't have Sale's track record, Verlander is almost six full years older and Bumgarner hasn't been the same pitcher due to injuries the last few seasons.
So, what would a deal look like and what will some important factors be?
1. The average annual value number will have to start with a '3.'
A $30 million yearly salary is the neighborhood for elite starters. Sale might not match the $34.4 million AAV landed by Zack Greinke a few years back at age 32, but he could come close.
Certainly, Sale can argue that he deserves as much as David Price ($31 million AAV), Clayton Kershaw ($31 million) and Max Scherzer ($30 million). Price, especially, is an important benchmark since it would be hard for the Sox to pay Sale less than they did Price, who signed with the Sox at age 30 and hasn't been nearly as good as Sale has been in the last two seasons.
Kershaw is another interesting comp. Last winter, he opted out of a contract and had the Dodgers re-write it by granting (essentially) one more year at approximately the same number. But a one-year extension is one thing and a new longer-term deal is another. And while Kershaw has seen significant drop-off in his performance and his velocity, with troubling and chronic back issues limiting his availability, Sale has been, in comparison, the picture of health.
2-The length of the deal will represent the biggest sticking point.
Even if the Red Sox concede Sale deserves an average annual salary of $30 million, they'll want to limit their exposure when it comes to how long they'll commit. The longer they go, the more risk they'll be taking on. It's one thing for a power pitcher to continue his dominance at 32 or 33; it's quite another to expect it will take place at 35 or 36. Verlander, who continues to flash a fastball in the upper 90s in his late 30s, is clearly the exception in this regard.
Sure, the Sox could keep the deal shorter and offer Sale a higher AAV. But that conveniently ignores two factors. First, it assumes that Sale would be OK with a shorter guarantee, forcing him back into the marketplace at 34 or older, when his appeal would be lessened. Secondly, there are important luxury tax consequences to a shorter deal.
If the Sox were to, say, make Sale's the highest-paid pitcher (by AAV, anyway) by offering three-years, $105 million, that new deal would increase the team's luxury tax concerns for this year even if the new deal wouldn't truly kick in until 2020. (Luxury tax computations are based on cumulative AAV, so even though Sale is making "only" $15 million in 2019 as the final year of a multi-year contract originally signed with the White Sox, that would jump considerably if an extension is reached).
It would surely send the Red Sox over the final luxury tax threshold to a point where every additional dollar spent over that figure would be taxed at 75 percent. That's a considerable additional expense to be factored into negotiations.
There's a (partial) way around this luxury tax mess -- give Sale a longer deal that is front-loaded for still-in-his-prime years while paying out less toward the end of the contract. But while that helps in the relative short-term, it still would mean that the Sox would have to cross their fingers about Sale in his mid-30s and beyond.
3. The Sox have to keep in mind that there are others waiting in line.
Sale will be the top-paid pitcher (or close to it) with any new deal -- this week, next month or next winter. Fine.
But he won't be the most expensive proposition facing them in the next two years. That distinction belongs to Mookie Betts, who will be 28 as his free agency arrives. And given that Manny Machado just hit the $300 million jackpot and Bryce Harper is expected to eclipse him, Betts will get more money than Sale. Likely a lot more.
Even if they succeed in retaining/extending both Sale and Betts in the near future, they could look forward to having three players (Price's deal has three more years to run) on the roster making in excess of $30 million in the coming years. That's roughly $100 million in annual payroll for just 12 percent of the roster.
It's going to be highly expensive to keep Sale. That much is a given. What they don't know is how painful -- financially speaking -- it will be, too.
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