Musings: Big Decisions Ahead For The Red Sox

By Dick Flavin

Boston Red Sox Poet Laureate

and New York Times Best Selling Author


I suppose that it’s too early to speculate on what will happen with the Red Sox once the

next baseball season begins, and I know it’s too late to do anything about what took place

in this baseball season. Why don’t we just refer to 2019 as “the recent unpleasantness”

and let it go at that? The timing, however, seems right to ruminate about the off-season

because it’s already upon us and it’s here before October, much sooner than we had either

hoped or expected.

There are major decisions to be made in the months ahead, not least of which is who will

be running the show. Signing a successor to Dave Dombrowski is priority number one for

the team because whoever that person turns out to be, he (or she!) will have to have a say

in all the other important decisions that have to be made.

If the Red Sox decide to hire that new head person from within the organization, it will be

one of the four who have been dubbed interim decision makers while the search for a

successor goes on. They are Brian O’Halloran, Eddie Romero, Zack Scott, and Raquel

Ferreira. All are well-thought of within the organization, but we have no idea of what the

mind-set of either John Henry or Tom Werner is – and they are the ultimate decision

makers. Ferreira is a particularly intriguing candidate since she would become the highest

ranking female executive in baseball history (There have been women owners.). She has

been with the organization for 21 years and is currently Senior Vice President of Major

and Minor League Operations, so her credentials are impressive.

Mike Hazen, an alumnus of the Red Sox baseball ops department, currently runs the

show for the Arizona Diamondbacks. He was quickly signed to a five year extension by

the D’backs once the Boston job opened up, thereby taking him out of consideration.

Theo Epstein, the president of the Cubs and former boy wonder of the Red Sox, is under

contract (and a big one it is) for two more years, so he doesn’t appear to be in the

running. Stay tuned; we should get a final decision sooner rather than later because

whoever the next head of baseball operations is will have a full plate of work in front of

him or her.

First on the agenda will be Mookie Betts. He doesn’t become a free agent until next year,

but a decision on him has to be made this year. He has made clear his commitment to

testing the market in 2020 and has already turned down several attempts the Red Sox

have made to sign him for the long term, so the question becomes do the Sox wait until

his free agency and risk losing him for just a draft choice, or do they deal him now in

order to get something of real value in return? Whoever Dave Dombrowski’s successor is

will spend some sleepless nights trying to figure that one out.

Then there is the matter of J.D. Martinez. He can opt out of his contract this year if he

thinks he can do better than the current one he has with the Red Sox, which pays him a

total of $109.95 million for five years and has three years to run. What happens with him

depends a lot on what happens with Mookie. It gets complicated.

Rick Porcello is a free agent this year. Although tantalzing us with an occasional gem, he

had a below average season in 2019, especially since he’s been making $20 million a

year. The Sox will probably let him go to free agency, but do they make him a qualifying

offer first? What if he takes it? It’s enough to give you a headache.

Jackie Bradley, Jr. will be a free agent in 2020. Do the Red Sox sign him to a contract

extension this off-season? Do they want to? He is, as everyone knows, an elite center

fielder, but he can be maddeningly inconsistent at the plate. The next head of baseball ops

will decide on his future sooner rather than later.

Brock Holt is a free agent this year. He is a model citizen on the field, in the clubhouse,

and in the community. His current contract pays him $3.5 million, he’s 31 years old, and

this is his chance to set up his family’s future. The Red Sox love him, but how much are

they willing to pay? That’s an important consideration because the Sox are determined to

get their payroll under the tax threshold to avoid paying excessive taxes in 2020, when

the threshold figure will be $208 million. That means they have to lop off around $40

million next year. That’s a tough row to hoe when you consider the big money contracts

that are already in place. David Price and Chris Sale, for example, will make $60 million

a year between them for the next three years. They combined for just 13 wins in 2019.


When you add in the fact that the farm system has been severely depleted in recent years

as the team has acquired big name stars, you have a whole a bushel of problems that need

solving. And they’ll drop right into the lap of the next head of baseball operations on his

or her first day on the job.

Oh, and the new person will not have what Dave Dombrowski had, which is complete

autonomy. Dombrowski had no one looking over his shoulder as he spent millions to

achieve his goal of capturing baseball’s holy grail. He did that, but the bill is now coming

due. You can bet that Sam Kennedy, the team’s CEO and the guy the guy in charge of

bringing in all the dough that baseball ops spends, will have an input into how that money

is put to work.

To be the chief honcho of baseball operations for the Boston Red Sox is to have one of

the most prestigious jobs in the game – and one of the toughest.

But look at it this way: at least Pablo Sandoval’s $17 million a year is finally coming off

the books.