Estimated Reading Time: 6 Minutes

The 2018 World Series feels a lot longer than 15 months ago, doesn’t it? At least to fans around Fenway Park.

This time last off-season, the Boston Red Sox were coming off one of the best campaigns in franchise history. They signed a few of their key pieces to long-term deals. Manager Alex Cora looked like a baseball guru. And President of Baseball Operations Dave Dombrowski could rest easier knowing his big spending had paid off in the short-term.

Boston has since turned into a bit of a dysfunctional mess, riddled with uncertainty across the board. Dombrowski was fired. Cora was outed amid baseball’s biggest scandal in recent memory. The team is currently pressed up against the dreaded salary cap threshold, and needs to cut money fast. Mookie Betts does not seem interested in sticking around long term. Boston also possesses one of baseball’s poorest-rated farm systems in terms of talent. And who the heck knows what’s going to become of Dustin Pedroia?

With so many questions and few answers, it seems like the 2020 season can go a number of different ways for Boston.

Where they stand

Here’s what we know for sure: Boston is coming off a disappointing 2019 campaign which saw them finish 84-78, 19 games behind New York for the top spot in the A.L. East. This poor showing got Dombrowski fired, and replaced by Chaim Bloom as the leader of Boston’s baseball operations. Bloom is considered a rising star in his profession, a master of analytics who churned out competitive Tampa teams for years with next to nothing of a payroll.

Unfortunately for Bloom, he’s not walking in to the prettiest of pictures. For one thing, they need a new manager. Names will get tossed around around in the coming weeks – Jason Varitek, Mike Lowell, Buck Showalter, Eduardo Perez – and right now there’s little use in speculating. The point here is that it’s likely the last of vacancies Boston’s front office expected to be filling before the season even begins.

But arguably equally as pressing for Bloom is Boston’s lack of young talent. Dombrowski’s prior wheeling and dealing over the years has depleted Boston’s farm system of assets. As it stands, the Red Sox only have a single prospect ranked among baseball’s Top 100 (Tristan Casas), and he is #77. Re-stocking the farm system is going to be problematic for a team that has holes to fill on the roster, and may face losses of future draft picks thanks to Cora’s nonsense.

A roster in flux

While they haven’t lost any core pieces yet this offseason, Boston has said good-bye to some familiar friends these last few weeks. Veteran Rick Porcello signed a one-year deal with the Mets. Backup catcher Sandy Leon was traded to the Indians. And infielders Steve Pearce, Mitch Moreland, and Brock Holt all remain free agents and seem unlikely to return. It’s these last three guys that point to a glaring need on the right side of the infield, especially when you consider the uncertainty around Pedroia.

Expect Boston to rely on Michael Chavis to pick up some of the slack here in 2020, having split time between both first and second base in 2019. Prospect Bobby Dalbec could be a potential first base candidate pending his Spring Training performance. And the newly signed Jose Peraza will see some time at second, and take on the role end of the bench utility guy. But Boston should be looking for another bat in any case, even if that means bringing Moreland back in the coming weeks. Luckily for the Red Sox, the left side of the infield is stone solid, with shortstop Xander Bogaerts and third baseman Rafael Devers both under contract and coming off monster offensive seasons.

Mookie, Mookie, Mookie…

Of course, Boston can rest assured that a few of the roster mainstays in recent memory will be back. J.D. Martinez passed on free agency and opted in to the third year of his contract. Andrew Benintendi is still under contract as well. And with the Red Sox avoiding arbitration with Jackie Bradley, Jr. and Mookie Betts, their outfield core seems to be intact for one more season. With the 7th ranked cumulative OF WAR (3.5) and Gold Glove nominations for Betts, Benintendi, and Bradley, the outfield was once again a key cog in the machine in 2019.

The question is, will it stay that way. The trade talks around Mookie Betts will certainly carry on throughout the season, as the former MVP seems uninterested in signing an extension in Boston. His record-setting arbitration deal ($27 million) keeps Betts here for at least the start of the season. But if the contractual impasse continues, expect Betts to become the centerpiece of a trade come the deadline. The Red Sox have every incentive to make this deal, despite his generational talent and status as a fan favorite. Trading a Betts-rental to either a contender and/or a team willing to sign him to a mega-contract next offseason could help to re-stock the farm system. But a more immediate itch the trade would scratch is to get Betts’ $27 million off their books. Which brings us too…

The good ol’ luxury tax

It may be the buzzword of the Boston offseason. Despite John Henry’s attempts to gaslight us, the Red Sox will likely do whatever they can to get back underneath the $208 million luxury tax threshold, and reset the penalty schedule back to zero. But that may be easier said than done. They owe David Price $32 million this season, another $30 to Chris Sale, and when you add in the $24 million for Martinez and $27 million for Betts… that’s over $100 million tied up in four guys. The team is nearly $20 million over the luxury tax threshold as it stands.

The problem for Boston is that they are going to have to eat money to cut money here. An aging Price and an often-injured Sale have insane amounts of money left on their deals ($96 million and $145 million, respectively). Even if they eat some of this cash in a trade with another team, they will still have to pay whoever it is they get in return. Eating too much money, therefore, doesn’t exactly help the cause. And getting one of those guys off the books, such as Price, would probably require coupling a player like Benintendi to him to sweeten the pot.

Which is why, trading Betts may be the best way to shed cash. Boston would not have to eat much of that salary, if anything. And a player of Betts’ caliber could command some serious draft picks or prospects in return. But things on this front seem to be moving at a snail’s pace. Boston does not seem to have any sense of which direction they would like to go.

So what can we expect in 2020?

Honestly, that’s probably harder than ever to predict for this team heading in to the season. Aside from the usual questions (will Sale stay healthy? does the bullpen have enough arms?), a plethora of new ones have emerged. Who is going to manage this team? Should the luxury tax take precedent over being competitive? Will we see a trade involving Betts and Price? Will the cheating scandal involving Cora bring a slew of penalties?

The Red Sox certainly have the talent to be competitive, and vie for a Wild Card berth at least. But it remains to be seen how much leeway ownership gives them to start the season. If they limp out of the gate, we may see a fire sale. On the other hand, maybe a new manager and a hot start is enough to entice Betts to sign a deal. Maybe Boston just gives the finger to the luxury tax. Who knows. It’s safe to say that the Red Sox have not found themselves at such a crossroads for some time. And whether they like it or not, they have only a few more weeks before they need to pick a path.