Should Red Sox be buyers or sellers at MLB trade deadline?

BOSTON, MA - APRIL 17: Dave Dombrowski the President of Baseball Operations of the Boston Red Sox walks towards the dugout during batting practice before a game against the Toronto Blue Jaysat Fenway Park on April 17, 2016 in Boston, Massachusetts. The Blue Jays won 5-3. (Photo by Rich Gagnon/Getty Images)
BOSTON, MA - APRIL 17: Dave Dombrowski the President of Baseball Operations of the Boston Red Sox walks towards the dugout during batting practice before a game against the Toronto Blue Jaysat Fenway Park on April 17, 2016 in Boston, Massachusetts. The Blue Jays won 5-3. (Photo by Rich Gagnon/Getty Images) /

In a season that’s been full of frustration, confusion, anger and then some, should the Boston Red Sox be buyers or sellers at this year’s trade deadline?

The Boston Red Sox sit in 3rd place in the American League East division with a record of 52-44. 9.5 games behind the first-place Yankees, and three games out of the final Wild Card spot, currently held by the Cleveland Indians.

Being completely honest, this season has been a disappointment but, that’s not to say things can’t change. However, if Boston is going to pull this off and be taken seriously as a threat to travel deep into October, they need to quickly figure out who and what they are.

This Red Sox team was one that was selected by many experts to make a return trip to the World Series in 2019, but the club has yet to show anything to prove that theory to potentially be true. There are other teams in the American League that have set the world on fire, the Yankees being one of them, and of course, the Houston Astros being another.

Boston has yet to build any momentum since the All-Star break, dropping two of three to the Dodgers before taking two out of three against the Blue Jays.

There are many things you can point to that stand out as the possible “Achilles heel” that’s dragged this team through the mud, but the bottom line is they just haven’t played cohesively as a team.

In 2018, Boston dominated and it seemed to be a new face or different aspect of the game that picked them up night in and night out. Now just one calendar year later, the Red Sox tend to be relying on one or the other. Either the offense puts up 10 runs to back up a bad bullpen or the pitching puts out a surprise performance to provide a boost for an offensive sputter.

So, that poses the toughest of questions: Will the Red Sox be buyers or sellers at the trade deadline?

Because at the very least, one of two things has to happen. Dombrowski and the front office either agree to spend the money and go over the luxury tax to officially go all-in on 2019 or they trade off some of their bigger pieces and get some prospects in return to boost the already extremely depleted farm system.

The foundation has already been laid out for potential franchise-altering decisions to be made heading into the 2020 season. Mookie Betts‘ contract situation is on the table to worry about and Dombrowski and the Red Sox will have a very, very big decision to make when it comes time to decide what to do regarding the reigning AL MVP. Is he worth the $30M he will likely commend in free agency? I’m not sure.

Could JD Martinez be on his way out if Boston decides to take the path towards getting younger? It certainly would be a plausible hypothesis, but it may be hard to find a taker on a contract in which a DH with back issues is still owed at least $19 million each of the next three seasons that will carry him up until his age-37 season.

Not only does Martinez have a hefty price tag as he ages, but David Price is also another member of the Red Sox ballclub that is set to rake in $32 million until the 2023 season. Yet another piece Dombrowski could ship off to a contender if he so chooses.

Boston could also decide to ship Jackie Bradley Jr. out of town. He will enter his final season before free agency next year and trading him would free up roughly $9 million from next year’s payroll for a potential move to get younger at the CF position in the offseason.

But, there’s always the flip side of that story, and if Dombrowski decides he wants to keep the young core of these Red Sox together, he could certainly make that happen, too.

Some say that with the addition of Andrew Cashner, who struggled a bit in his Red Sox debut, that proves Boston is “all in” on this season, but does that trade really help Boston out?

The fifth spot in the Red Sox rotation has been a revolving door over the course of the past three seasons or so, and Cashner is just the latest name to get a shot. It’s the bullpen that needs the most tightening up and Boston shouldn’t expect to go anywhere in the postseason without some sort of a major deal to add a true power arm that can lock down ballgames.

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The 2019 season is a bit reminiscent of the 2004 Red Sox team that stumbled in the dog days of summer before shipping off star shortstop Nomar Garciaparra to the Cubs in a four-team blockbuster that landed the Sox Orlando Cabrera and Doug Mientkiewicz. After that deal, Boston took off and the rest was history.

It almost feels like that sort of trade is on the horizon for this Red Sox team. A deal that will shake this team to the very core and the player that most resembles Nomar, who was 31 years of age at the time of the deal, is Mookie Betts. A huge contract decision will be arising soon and one that Boston may not want to deal with. While the trade may not be one that fans would take terribly kindly to, if it winds up propelling Boston to a postseason run such as it did in 2004, nobody would be complaining too much.

Meanwhile, as we sit and wait for a deal that may or may not take place, Boston is still very much in the thick of the Wild Card race. It keeps summer baseball entertaining, to say the least, amid all the frustration, but that’s exactly why the new playoff format was created. For entertainment. To give teams that aren’t truly at the top tier of competition something to hold onto as the season rolls into August and September.

Let’s be honest, are the Wild Card teams ever really taken seriously? Sure, I realize that sometimes every once in a while one of those ballclubs can go on a ‘Cinderella Run’ deep into October, but for the most part, it’s always the teams that win their respective divisions that get the most attention.

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Boston has never been a team to be an afterthought and that’s something that Dombrowski will have to think about long and hard when deciding over the course of the next two weeks if this Boston Red Sox ballclub is truly built for the long haul. There are valuable pieces out there but the moves have to be all or nothing. The Red Sox already have the highest payroll in baseball, so they can’t be taking on any more contracts that won’t help them work towards a championship in the end. What moves shall be made, and whom they will affect, remains to be seen.