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5 questions Red Sox must answer this offseason

@MikeLupica
November 23, 2019

In terms of the stakes, and the implications for the Red Sox going forward, there hasn’t been an offseason this important since John Henry, Tom Werner and Larry Lucchino basically reinvented the club when they took over ownership 18 years ago this December. Since then, Boston has gone to four

In terms of the stakes, and the implications for the Red Sox going forward, there hasn’t been an offseason this important since John Henry, Tom Werner and Larry Lucchino basically reinvented the club when they took over ownership 18 years ago this December. Since then, Boston has gone to four World Series and won them all, and twice lost Game 7 in the American League Championship Series.

But a lot has happened since the Red Sox won their last World Series just 13 months ago. The fall from the top of the AL East and out of the playoffs was dramatic enough that Dave Dombrowski, the president of baseball operations in Boston, didn’t even make it through the next season.

So Dombrowski is gone, replaced by 36-year-old Chaim Bloom, whom the Red Sox hired away from the Rays, who not only were 12 games better than the Red Sox this past season, but managed to do that with the smallest payroll in the sport. The Red Sox had the highest.

When Henry and Werner met with the media a couple of weeks after Dombrowski was let go, one of the things Henry said was that “[We] need to be under the [luxury-tax threshold of $208 million].”

In the same session, Werner qualified that slightly by saying that it was a preference, not a new ordinance passed in Boston.

So Bloom, whom the Red Sox are hoping can be the kind of front-office boy wonder that Theo Epstein once was, comes through the door on Jersey Street facing a lot of questions this offseason.

Here are the 5 biggest:

1. What to do about Mookie Betts?
In 2018, Betts was the Most Valuable Player in the American League, and he had a season in which he tried to out-Trout Mike Trout, in terms of all-around performance. Betts is already one of the most talented players in Red Sox history and, if he stays, could turn out to be the next-generation David Ortiz.

But Betts is eligible to become a free agent after this season. He is going to want to get paid, and big, and if that doesn’t mean getting paid the way Trout did in Anaheim, it will certainly mean getting paid the way Bryce Harper and Manny Machado did last winter.

Henry, Werner and Bloom need to start getting an idea now, and certainly before the next Trade Deadline, whether the two sides can find common ground on extending Betts. They tried to extend him once, in 2017. Now what Betts wants and what Henry wants in terms of payroll might be on a collision course.

It would have seemed impossible, in the afterglow of the last World Series, that the Red Sox would trade Betts. It is no longer impossible. This is the question that will dominate all the others around Boston going into 2020.

He’s not Trout. No one is. But he’s their Trout. The Angels decided to keep Trout around forever. But we’ve been reminded again over the past year that nothing is forever at Fenway Park.

2. What to do about the payroll?
This question doesn’t resonate with Red Sox fans the way the one about Betts does, but you can’t discuss one without the other. Can Bloom get the payroll under the luxury-tax threshold level of $208 million (down from the $226 million Boston spent last season)? Bloom’s job didn’t get any easier when J.D. Martinez opted into a $23.75 million deal for 2020.

The Red Sox hired Bloom because he was clearly a math whiz in St. Petersburg: $68 million spent, 96 games won. Math class now very much in session at Fenway.

3. What to do about David Price?
Price is 34, had wrist issues last season coming off the postseason of his life, started just 22 games in 2019 and won seven. The left-hander made just one start after Aug. 4. His base salary for 2020, the fifth year of the seven year, $217 million deal he signed with the Red Sox, is $32 million. If there is a big contract Boston might be able to move, it is his. But Bloom has to find out if there is any market for Price, at that money, coming off a season like the one he just had. And even if there is a market, the Red Sox will likely have to eat some salary, which affects the whole luxury-tax issue.

4. Where do the Red Sox find starting pitching, even if Price stays?
Chris Sale (6-11, 4.40 ERA) was hurt for much of last season, but he has stayed away from major surgery. For now. Rick Porcello was disappointing and is now a free agent. Price got hurt. The Red Sox had one reliable starter in 2019, Eduardo Rodriguez, who had the season of his life and won 19 games. Yankee fans always talk about the need for starting pitching. Their rotation looks stronger than the Nationals’ compared to Boston’s, at least right now.

5. How does Bloom fill the other holes, and not just at Fenway?
The Red Sox don’t have a regular first baseman. Don’t know who’s playing second. Don’t know who the ace utility guy is if free agent Brock Holt leaves. And the farm system isn’t deep. How does Bloom solve all those problems without losing Draft picks in the process?

Red Sox fans know. This is the short list of questions for Bloom. But here’s one more his fans, spoiled by nearly decades of success, want answered:

How does he make up 19 games in the standings on the New York Yankees?

Mike Lupica is a columnist for MLB.com.