1:17pm: Werner and principal owner John Henry met with the Boston media today and indicated that they’ve not only discussed a long-term deal with Sale but also with Xander Bogaerts (link via the Globe’s Peter Abraham). Like Sale, Bogaerts is slated to become a free agent at the end of the 2019 season. The ownership reps noted that while they’d love to be able to keep each of Sale, Bogaerts and Mookie Betts in Red Sox uniform for the long haul, such a scenario probably isn’t realistic.
Perhaps of note, when asked about the last top-tier lefty the Sox had on the cusp of free agency, Henry candidly acknowledged that the Red Sox “blew it” when trying to work out an extension with Jon Lester prior to 2014 — Lester’s last in Boston.
8:38am: The Red Sox and ace Chris Sale have had “private” discussions about a contract extension, chairman Tom Werner said in an appearance on WEEI’s Mut & Callahan show this morning (Twitter link, with audio). Sale is currently slated to earn $15MM in 2019 and will become a free agent next offseason. He said last week that the Red Sox had not yet initiated extension negotiations.
Clearly, whether it’s in the form of an extension or in an open-market setting, Sale is in position to command a substantial raise — likely one that would at least double his salary. The seven-time All-Star, who will turn 30 years old in March, has finished in the top five in American League Cy Young voting in each of the past six seasons and has never turned in an ERA higher than 2015’s mark of 3.41. It’s somewhat surprising that Sale has never actually taken home the Cy Young hardware, though his excellence and consistency still make him a solid bet to do so at some point in his career; Sale’s 10.88 K/9 and 5.31 K/BB ratio are both the best all-time marks for any pitcher to ever have thrown 1000 MLB innings.
A new contract for Sale would begin in his age-31 season, so the length of the pact could be a potential sticking point in talks. Teams throughout the league have shown increasing resistance to guaranteeing money to players into their late 30s, and it’s been fairly rare to see five-, six- and seven-year deals that guarantee pitchers into their age-37 seasons. That said, assuming a healthy year from Sale, he could have a case to to top Zack Greinke’s current $34.4MM annual salary record. While he hasn’t previously called that a goal, Sale did recently express the importance of furthering the market for future players.
“You want to do right by the guys who are coming next year, two years, 10 years down the road because you kind of set the bar and the next guy who comes along either gets to that bar or sets it a little more,” Sale said in his own appearance on Mut & Callahan last week. “That’s kind of the brotherhood of being a Major League Baseball player.”
A healthy 2019 season will be of particular importance for Sale in 2019. While he’s long been a consistent force in the rotation with both the White Sox and Red Sox, he was limited to 27 starts last year — his fewest since 2015 — and went through a pair of stints on the disabled list as a result of inflammation in his left shoulder. Sale certainly looked healthy when striking out the side to close out Boston’s World Series win over the Dodgers. though, and he’s now had the benefit of a full offseason to rest that mildly problematic shoulder.
It’s worth noting that an extension for Sale would push the Red Sox into the top luxury tax penalization bracket. As I explored recently when looking at what it’d actually cost the Sox to re-sign Craig Kimbrel — the taxes on any such signing could top $10MM — Boston is only about $6MM south of that $246MM barrier. Viewed through that lens, the Sox may actually prefer to wait until the end of the season, although in doing so they’d also be running the risk of allowing Sale to test the open market.