Red Sox Winter Meetings Primer: Burning Questions, Bold Prediction For Offseason

It’s the most wonderful time of the year, and we’re not talking about the holidays.

We’re talking, of course, about Major League Baseball’s winter meetings, which should really start to heat up Monday in National Harbor, Md. A bunch of MLB executives gathering in a convention center might not seem thrilling, but the winter meetings usually mark the unofficial start of the offseason, when teams start taking a serious look at addressing their needs via free agency and trades.

The Boston Red Sox certainly fall in that category. Boston won an impressive 93 games last season, but after getting swept out of the American League Division Series, it still has plenty of holes to fill this winter — starting with a massive one in the middle of its lineup.

With that in mind, let’s break down what to keep an eye on at next week’s winter meetings.

THREE BURNING QUESTIONS
What to do at designated hitter?
We already alluded to it, but replacing David Ortiz should be the Red Sox’s biggest offseason priority. Despite Ortiz’s best efforts, it’s looking less likely that replacement will be Edwin Encarnacion, as the Toronto Blue Jays slugger-turned-free agent reportedly wants a long-term contract that Boston would rather not dish out.

Carlos Beltran is an intriguing short-term option at DH, but the Red Sox don’t necessarily have to fill the position externally: President of baseball operations Dave Dombrowski has suggested designated hitter could be a timeshare, possibly involving Hanley Ramirez and Pablo Sandoval. Are the Sox content with what they have, or will they sign a guy like Beltran to boost their offense?

More starting pitchers needed?
The Red Sox could use more starting pitch depth, but finding it will be easier said than done. This winter’s free-agent pitching class is historically dry, with Rich Hill and Ivan Nova among the best available free agents. That puts Dombrowski in a bit of a bind: Does he overpay for a back-end starter or decline to upgrade a rotation that has big question marks outside Rick Porcello and David Price?

Can the Sox fix their bullpen?
The good news: Carson Smith likely will return from Tommy John surgery next season. The bad news: Boston needs more bullpen help outside Smith. The Sox’s back end was too inconsistent in 2016, and the team might need to fill gaps with Koji Uehara, Junichi Tazawa and Brad Ziegler entering free agency.

An eighth-inning setup man behind Craig Kimbrel should be Dombrowski’s top bullpen target, and there are plenty out there in the likes of Sergio Romo, Joaquin Benoit and Greg Holland, to name a few. Will Dombrowski take a chance on one of those players or stick with an internal option like Joe Kelly?

ONE BOLD PREDICTION
The Red Sox make a run at a Chicago White Sox pitcher.
The MLB offseason isn’t limited to the free agent market, and Chris Sale and Jose Quintana are two tantalizing trade targets in a tough offseason for pitching. Boston has been involved in Sale rumors before, and after another bad season for the White Sox in 2016, this might be the year Chicago parts with its ace. If Dombrowski can’t land the big one, he could seek a solid consolation prize in Quintana, offering the White Sox one of Boston’s many prospects in return.

Thumbnail photo via Mark J. Rebilas/USA TODAY Sports Images

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