Red Sox: Five biggest offseason questions heading into December

BOSTON, MASSACHUSETTS - SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS - SEPTEMBER 04: Mookie Betts #50 of the Boston Red Sox hits a three run home run against the Minnesota Twins during the second inning at Fenway Park on September 04, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
6 of 6
red sox
BOSTON, MA – SEPTEMBER 27: John Henry, Tom Werner and Larry Lucchino share a laugh as Lucchino was being honored for his last home game as Red Sox CEO/President before a game against the Baltimore Orioles Fenway Park on September 27, 2015 in Boston, Massachusetts. (Photo by Rich Gagnon/Getty Images)

Will the Red Sox go for the postseason or cut payroll?

This offseason will show the priority of the Red Sox front office. Trading Betts and cutting other players in order to save on the luxury tax would signify that they are going to try and cut payroll. Sticking with this core and hoping they can replicate the magical 2018 season shows that winning is still the number one priority.

Paying a small tax to keep stars like Betts is definitely worth it as he is a once in a lifetime talent. I believe the Red Sox will ultimately realize there is no way to completely avoid paying the luxury tax this season, but a more realistic plan would to be shave little bits of payroll, such as cutting JBJ, and make the goal to get under the tax in a year or two.

While I am concerned that Chaim Bloom was brought in to begin a rebuilding process and reload for a few years, I am still confident the Red Sox will be contenders in the 2020 season. With a rotation that should come back strong, an improved bullpen, and a powerful lineup, the Red Sox won’t be able to avoid the luxury tax.

Altogether, I don’t think the Red Sox will be able to cut all of the payroll they want as they will still try to win. Similar to what Andrew Friedman did with the Dodgers, the Red Sox will be contenders for many years while still paying lots of money in the present.

Prediction: Red Sox will pay the luxury tax in 2020 in order to remain contenders

Schedule