Red Sox

Red Sox

Dave Dombrowski couldn't resist getting involved in Extension Season.

To cap a busy week of franchise cornerstones signing long-term contract extensions -- Mike Trout, Alex Bregman and Paul Goldschmidt, to name a few -- reports surfaced Friday that the Boston Red Sox have agreed to an extension with ace Chris Sale worth $145 million over five years.

That's a lot of cash to commit to a player who turns 30 in eight days. But Sale has earned his price tag, posting a 2.56 ERA over his two seasons in Boston while finishing in the top five in American League Cy Young voting in both years.

Locking up their ace also allows the Red Sox to check the top item off their lengthy to-do list for next winter. And it's lengthy; here's a list of pending free agents after the 2019 season:

-- OF/DH J.D. Martinez (opt-out clause)
-- SS Xander Bogaerts
-- SP Rick Porcello
-- 1B Mitch Moreland
-- 2B Eduardo Nunez
-- UTIL Brock Holt
-- 1B Steve Pearce
-- RP Tyler Thornburg

Dombrowski admitted Thursday that Boston likely won't be able to re-sign one of Sale, Porcello, Martinez and Bogaerts. So, with Sale extended, which of that trio would be the odd man out?

Considering Sale, David Price, Nathan Eovaldi and Eduardo Rodriguez all reportedly are under contract through next season for a combined $86 million, you could make a case it's Porcello.


Porcello has a 50-28 record in Boston over a three-year tenure that includes a Cy Young award. He's also an established leader in the clubhouse. His ERA has been north of 4.00 in each of the last two seasons, though, so it just might not make sense for Boston to pay him what he wants in free agency when it could pursue a back-end starter at a lower cost, especially if that gives the club flexibility to retain Martinez and re-sign Bogaerts.

There's another factor looming, of course: Mookie Betts' expected mega-payday. The Red Sox outfielder is set to hit free agency in 2020 and could command a contract in the $35 million-per-year range. If that deal is with Boston, the Sox would have three players under contract for north of $60 million combined from 2020 to at least 2022.

Dombrowski has been willing to spend big on pitching in Boston, and last year's World Series title certainly validates that strategy. But extending Sale may force the Red Sox's front office to make some tough decisions elsewhere on the pitching staff.

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