The Monday Baseball Column: A closer look at Red Sox' trade options

Rob Bradford
December 09, 2019 - 8:51 am

It feels like something is going to happen at these Winter Meetings, but figuring out exactly what is a bit of a dilemma.

While it's far from a mystery that the likes of the two Los Angeles teams and the Yankees will be throwing gobs of cash at free agents such as Gerrit Cole, Stephen Strasburg and Anthony Rendon, that world will seem foreign to the Red Sox.

There will be no semi-secret lunches with high-priced free agents, or bidding wars the likes of which the Sox experienced the last time these things were in the Manchester Grand Hyatt, with Boston serving as the runner-ups for the services of Andrew Miller and Jon Lester.

Even the lower tier of free agent investments seem like a reach for the Red Sox as currently constituted. While there is no doubt they would love to have the likes of Brock Holt and/or Rick Porcello back as clubhouse staples finding the financial flexibility to do so doesn't seem feasible at the moment.

A guy like Josh Lindbloom -- the 32-year-old pitcher who last performed in the majors in 2014 but has been rejuvenated in the Korean Baseball League -- would normally be an intriguing option for the Red Sox' rotation's final spot. But he will cost money, and that doesn't line up with the Sox' current world.

This, however, doesn't mean Chaim Bloom is going to be walking out of San Diego with the exact same team he walked in with. It just means we are left trying to put together a much more complex puzzle than we're used to this time of year.

Simply put, we're guessing about trades instead of which free agents will be getting John Henry's money.    

In some ways, this is like that Winter Meetings in San Diego leading into the 2015 season. That time around the final day gave us two trades nobody saw coming, dealing for Porcello and Wade Miley. It's just that there won't be the buzz involving free agents that is usually a big part of the equation.

Another difference this time around is that when we're talking trades it isn't along the lines of giving up the promise of minor-leaguers. No, this is about trying to identify which big leaguer(s) are going to be used to manage what has become the Red Sox' suddenly uncomfortable existence.

So it would seem to be a worthy exercise to offer some perspective when it comes to each trade candidate on the Red Sox' roster:

Andrew Benintendi

His name hasn't really been in many rumors up until recently, and for good reason. He is perceived as part of the solution at a reasonable rate. But The Athletic's Ken Rosenthal used Benintendi as an example of the type of young, controllable player the Red Sox might have to include in a deal involving some high-priced pitchers. If the Sox had a turn-key solution for a replacement (Jarren Duran isn't quite there) this might be palatable. Yet despite the left fielder's slight offensive and defensive downturns in 2019 he is a proven positive who might simply be coming off a wake-up call-type of season.

David Price

This is the contract that makes Benintendi's name surfaced at all. Bloom knows that as valuable as a veteran starting pitcher like Price can be, it's probably worth more important to find other uses for Price's money while getting creative in the rotation. Unlike when Lester left, the Red Sox wouldn't be devoid of a top of the rotation if Price left thanks to the presence of Chris Sale (even with his uncertainties) and Eduardo Rodriguez. The problem is that this isn't just about the money. Any team getting Price will be inheriting some uneasiness when it comes to the lefty's physical status. The 34-year-old didn't pitch past Sept. 1 last season and hasn't made more than 22 starts in two of the four years he has been in Boston. The Red Sox said they want to get creative. In this case, it might be asking Bloom to evolve into Thomas Edison, Walt Disney, Albert Einstein and Steve Jobs all wrapped up into one.

Nathan Eovaldi

Ditto. The interesting difference in Eovaldi's case compared to Price is how the Red Sox' might get a team to view the righty. While the old way of thinking for most teams would have been to prioritize Price's past performance, more and more clubs are actually prioritizing potential. That was a big reason Eovaldi got the contract he did. The issue is that even with all of Eovaldi's promise there simply isn't enough health/production to eliminate needing another significant piece coming from the Red Sox in any deal.

Mookie Betts

Theo Epstein's quote heading into the contract years of Pedro Martinez, Jason Varitek, Derek Lowe and Nomar Garciaparra was this: "Never underestimate the value of a season." So true, which we are most likely going to be reminded of thanks to Betts' situation. The outfielder is simply worth more to the Red Sox even with just one year left on his deal than he would be in a trade at this point. Sure, a team might pop up with some sort of deal that represents a healthy chunk of the Sox' reset, but with one year of commitment at $27 million -- on top of whatever they had to give up to get Betts' services -- finding such a club seems unlikely. When spring training ended last season the Red Sox had offered Betts A LOT of money. Betts was asking for A LOT more. That likely hasn't changed. But it is what it is at this point: a pivotal season when it comes to defining what Betts is and will be, and likely doing so in a Red Sox uniform.

Jackie Bradley Jr. 

The thinking is that the Red Sox had no qualms tendering Bradley Jr. a contract despite what figures to be a $11 million price tag for 2020 because they are confident there is a market for him. There has almost always been a ton of interest in Bradley Jr. at the Winter Meetings with the Red Sox rebuffing inquiries at pretty much every turn. This is a bit different. The Sox still value Bradley Jr. but yet another season of uncomfortable offensive production on top of the financial concerns would seemingly lead to the Sox becoming more proactive this time around. The question is this: Does a team believe giving up anything for one year of Bradley Jr. at that price and without proof he can emerge from the bottom of a batting order is worth it?

J.D. Martinez

Most knew that the Red Sox' plan of attack this offseason was going to be shaped in large part by Martinez's decision to opt in or out of his current deal. He opted in, putting $23.75 million on the books for 2020. While the outfielder/DH would seemingly be perceived as a possible financial flexibility considering the kind of production all teams would value, the chance of a trade are slim. Martinez has no-trade rights for three teams of his choosing. And considering that is just about the number of clubs who would pay top-level money for a player who would primarily serve as a designated hitter (White Sox, Yankees, Rangers) it is an obstacle that most likely limits that option for the Red Sox.

Christian Vazquez

Not in play considering, 1. How catchers are more valuable than ever; 2. What seems to be a team-friendly contract; 3. He seems to be emerging into the kind of catcher that can be leaned on for 120-plus games; 4. There is no logical replacement.

Eduardo Rodriguez

To Dave Dombrowski's credit, he told teams at the last few Winter Meetings that Rodriguez -- even with his inconsistencies -- was not going to be part of trade conversations. While Bloom probably takes the "never say never" narrative to level of reality, the idea of dealing the lefty still is probably at the bottom of the to-do list.

Rafael Devers

Think extension, not trade.

Xander Bogaerts

Yes, Bogaerts makes a good chunk of money ($20 million a season). But considering the position he plays, the production he put forth in 2019, his age and emerging presence as a bonafide leader it makes no sense to entertain the idea that that cash would be better served being spent elsewhere.

Michael Chavis/Bobby Dalbec

Both players are major leaguers with some upside, but not viewed in big league circles as centerpieces in a big trade. What they might represent are those kind assets needed to offload the likes of Price or Eovaldi, which is unfortunate for the Red Sox who seemingly have immediate spots for each player's skill-set.


Just more than a year ago Pearce committed to a one-year, $6.25 million deal with the Red Sox. It made a lot of sense for the team considering he represented the kind of right-handed bat that would complement Mitch Moreland at first base. (And it didn't hurt that he had left a pretty positive impression thanks to a flurry of World Series heroics.) And the player got the chance to perform in his preferred destination while setting himself up for a chance to keep exhibiting his value.

As you know by now things didn't pan out. Pearce was injured from the get-go and never could find the field long enough to help a Red Sox' first base position that ended up with the ninth-worst OPS in baseball.


Pearce passed on via text to that he is "unofficially retired." 

If this is it for the 36-year-old he will have played 786 total big league games while getting his 10 years of service time thanks to this 2019 campaign. Why is 10 years so important to a guy like Pearce besides just having garnered the respect that comes with longevity? A fully-vested pension.

The pension allows members a minimum of just about $68,000 a year for those who start drawing from it at the age of 45. It goes up to $220,000 a year on a sliding scale if the participant chooses to wait for their payoffs to kick until age 62. (Pearce made an estimated $29 million over 13 major league seasons.)


In the midst of last year's Winter Meetings Bradley Jr. couldn't hide his excitement.

"This is the first time I heard any of this stuff," said Bradley Jr. told "What I’ve been taught my whole life is completely wrong. It’s scary to say that, but it’s wrong. I feel fortunate enough to make it this far doing it wrong."

Bradley Jr. was in the midst of getting offseason instructor Craig Wallenbrock, one of the private hitting instructors J.D. Martinez had relied on during his ascension to becoming one of the game's elite hitters. The alternations, however, didn't translate like the outfielder had hoped, with Bradley Jr. finishing 2019 at just about his career average, hitting .225 with 21 homers and a .738 OPS, striking out a career-high 155 times.

His story wasn't an isolated one.

Travis Shaw took the same path last offseason (at the recommendation of some Red Sox players), also going out to Los Angeles to revamp his swing. 

"There are a lot of hitting gurus out there right now and I actually went to one last offseason, and I think that was part of the reason I struggled a little bit," Shaw said on the Bradfo Sho podcast. "I tried to fix something that really didn't need fixed. Some things work for certain guys. You just have to know your swing. If it doesn't work for you then you have to find something that works for you and just stick with it.

"I went out there and everything they told me made complete sense. I loved the ideas and everything but for some reason it just didn't work for me. I did it all last offseason trying to perfect that, and then got off to a slow and just couldn't get back to where I was before. Toward the end of the year, I felt like I was in a good place, back to where I was in '17 and '18 and now this offseason I've completely reset and started to hit now and it feels back to normal what my own swing was."

Shaw's 2019 struggles have been well-documented, especially of late considering he has found himself as a free agent. (Yes, the Red Sox have called.) But the path to his downturn can seemingly be traced to taking what has been a popular path for many major leaguers of late.

"It just didn't work," he said. "I didn't end up doing it. I built it into my habits a little bit because I worked on it so much this past offseason and then I get into spring training and it wasn't really working so I kind of bailed on it in the middle of spring training. I was able to have some success in spring training, hit the ball well. Struck out more than I was used to. But for some reason, there was a minor little mechanical issue all season we couldn't seem to grasp and get a hold of. But toward the end of the year, it was fixed a little bit and I'm very confident where it needs to be."


There seems to be more money being thrown around baseball heading into this year's Winter Meetings than the last two. So, let's take a look:

Free-agent money spent leading into Winter Meetings (including extensions) - 2018: $469 million ($140 million coming from extensions given to Clayton Kershaw and Carlos Carrasco); 2019: $608 million ($122 million coming from extensions given to Jose Abreu, Evan White and Aroldis Chapman).

To date, there have been 23 trades made since the end of the World Series, the same number executed heading into last year's Meetings.