Hypothetical Scenario: A 2019 Red Sox Fire Sale

Let me preface this entire piece by stating that THIS IS NOT A PREDICTION. I don’t believe for one second that the Red Sox will still be below .500 a month from now, much less by the July trade deadline. However, I enjoy playing the “What if?” game, and since many Boston fans tend to be excessively pessimistic when it comes to the Beantown’s favorite baseball team, I’ll attempt to humor the cynical portion of our target audience in this piece.

Our previous championship team faced a similar fate when the 2014 Red Sox started the season by losing 29 of their first 49 games. By the All-Star break, Ben Cherington began raising the proverbial white flag in what would be his final full season as Red Sox general manager. Of course, the writing was on the wall for that squad. After all, there are numerous reasons why the 2012 Red Sox also finished dead last in the AL East. Nevertheless, scrapping the roster for parts and shipping out useful pieces to contenders netted names like Heath Hembree, Joe Kelly, and Eduardo Rodriguez, as well as Yoenis Cespedes, who would later be flipped for Rick Porcello.

Dave Dombrowski – the same man who sent Porcello to Boston in exchange for Cespedes – also has experience in this department. Dealin’ Dave was forced to dismantle the 1997 Florida Marlins as quickly as he had assembled the roster. Of course, circumstances were different back then. Cheap ownership mandated that the team slash payroll in lieu of competing to the best of the organization’s abilities. That isn’t the case with the 2018-19 Boston Red Sox. We’ll simply assume, for this exercise, that a perfect storm of bad luck and injuries derailed the team’s dreams of repeating.

So who stays and who goes? Obviously, the Red Sox hope to be competitive in 2020 and beyond. There’s no sense in committing 8-figure salaries to Chris Sale and Xander Bogaerts (on top of David Price, Nathan Eovaldi, and J.D. Martinez, provided he doesn’t opt out of his current deal) for multiple years if they aren’t a part of the long-term plan.

The key here is to first identify who’s expendable: the players who either 1) aren’t under contract for the 2020 season, or 2) could be replaced relatively quickly while yielding a significant return. From there, each player’s individual market must be evaluated based on other teams’ needs. Once we assess every potential trade partner’s assets, all that’s left to do is negotiate a deal. Let’s give it a try…

Rick Porcello

We already know that Boston’s current president of baseball operations has no problem dealing away Porcello. As I mentioned earlier, he’s already done it once before. The longest-tenured member of the Red Sox rotation was very clear in stating his desire to remain with the team beyond this season, even going so far as to say he’d take a discount. Unfortunately, a slight discount might not be enough.

The 2016 American League Cy Young Award winner signed a 4-year, $88 million extension upon his arrival in December 2014, and could probably fetch a similar deal on the open market following another solid 2019 campaign. Assuming we don’t trade him before season’s end, we should extend him a qualifying offer, in my opinion. Beyond that, spending more money to keep Porcello around would be reckless.

Currently, Porcello is already MLB’s 29th highest paid player in 2019, and the second-highest paid pitcher on Boston’s 2019 payroll. Chris Sale will play out 2019 for $15 million, per the terms of his contract, but the extension he recently signed doubles that figure in 2020 to $30 million. Add David Price’s $31 million, Nathan Eovaldi’s $17 million, plus whatever raise Eduardo Rodriguez (making $4.3 million in 2019) will receive via arbitration, and you’re looking at a 4-man rotation totaling over $83 million. Accounting isn’t my forte, but allocating nearly 40% of the club’s salary cap “predetermined payroll threshold” to 16% of the club’s active roster doesn’t sound like an equation for success. It’s still going to happen, regardless, but the budget for Boston’s 5th starter will be modest; perhaps too modest for Porcello.

So Porcello won’t be back. Might as well trade him now and get something for him if we’re holding a fire sale. Competitive teams – even the ones with solid rotations – are always looking for depth and reinforcements in July. The Eovaldi trade caught me off guard last season, based on how our rotation was performing at the time, but the move sure paid off, and I’m certain that teams in the mix will see Porcello as that potential finishing touch to their respective rosters.

Basically, any team in the playoff hunt might give Dombrowski a call about Porcello. He is only a rental, and an expensive one at that, so kicking in some money would leverage Boston’s ability to ask for premiere prospects in return. Teams with solid rotations and/or thin farm systems (i.e. the Cubs, Indians, and Nationals) will likely want to hold onto their best young talent. However, teams that are eyeing October without a bona fide postseason-experienced clubhouse leader at the front of their rotation (teams like the Atlanta Braves and San Diego Padres; coincidentally Bleacher Report’s top 2 farm systems entering 2019) could turn to the Red Sox to fill that void.

I’m leaning towards the Padres because 1) the NL West is the weakest it’s been in years. The Padres seem to realize this, and appear to be making their long-awaited push after signing Eric Hosmer and Manny Machado in consecutive offseasons, then calling up Fernando Tatis, Jr. instead of stashing him the minors in order to manipulate his service time. And 2) I fully expect the Braves to regress and miss the playoffs after a surprising 2018 NL East title, so they wouldn’t be “buyers” at the trade deadline.

Dombrowski has sent several prospects A.J. Preller’s way over the past few years, so they obviously have a good relationship. I’d like a do-over on the Pomeranz trade, which the league offered Boston an opportunity to overturn. I’ll send Porcello and some salary relief to the Padres in exchange for former Sox International signee Anderson Espinoza.

Brock Holt

One of my personal favorites in terms of personalities on the roster, it pains me to write this section. Between completing the only cycle in World Series history and his clubhouse antics, the 2015 All-Star will leave fans like me with many fond memories, but the fact of the matter is that Tzu-Wei Lin can do just about anything the pending free agent can do, and for about $3 million less.

The trade partner for this player seems painfully obvious to me, given that the Brewers are still trying to decide between Mike Moustakas and Travis Shaw at second base, both of whom belong at third. I don’t think that asking for Braden Webb – a 2016 third round pick with one Tommy John surgery already under his belt – in return for the BrockStar is unreasonable.

Matt Barnes

But wait, Barnes isn’t a free agent until after the 2021 season. Why would we trade him now, especially when the bullpen is a weakness for the Red Sox? I know it sounds counter-intuitive on the surface, but stay with me.

My philosophy regarding bullpens is similar to Dombrowski’s. It seems like every year, at least one “stud” closer falls off the wagon, and every year, at least one “nobody” magically bursts onto the scene with a ridiculous strikeout rate and makes the All-Star team. For 2018, think Ken Giles and Josh Hader, respectively. My point is that, with the exception of generational talents like Craig Kimbrel, relief pitchers are pretty interchangeable, at least more so than any other position in baseball.

If you keep up with the farm system, you know that it’s only a matter of time until Durbin Feltman inherits the role of Red Sox closer. Out of fairness to the 28-year-old former first round pick, I’d rather see Barnes sent to another organization, where another manager can redefine his role, than have him sit back and watch as a younger, less-polished arm leapfrog him on the depth chart.

That’s not to say that we should trade Barnes just for the sake of trading him. This notion is also predicated on the assumption that Barnes performs well in his first year as Boston’s closer, raising his value to the point where we could get a quality player – either a Top 100 prospect or an established MLB player – back in return.

Though I would prefer to send him to the National League where he can only contend with the Sox every so often, the Phillies, Mets, Nationals, Brewers, Cardinals, Rockies, and Dodgers all appear to have the makings of a decent bullpen. The Cubs (or Braves, depending on how you think they’ll do in 2019) could potentially be a match, but I think one American League club makes even more sense.

The Cleveland Indians lost both Andrew Miller and Cody Allen this offseason, but didn’t really do much to fill the void left by the two pitchers. They also have a track record of trading for a reliever with multiple years of control after pulling the trigger on Brad Hand last July. With Minnesota looking to rebound from an ugly 2018 disappointment, and the White Sox boasting an elite farm system that could be ready to contend at the MLB level as early as next year, Mike Chernoff and Terry Francona must be able to see that their window is closing. Every arm in their rotation is capable of a quality start each time out, but getting from the 6th or 7th inning to Brad Hand in the 9th may prove to be difficult.

If Cleveland would be willing to give us Triston McKenzie for Matt Barnes, we should take the deal immediately, even if when we are in the playoff hunt. Yes, even though the move would almost certainly further damage our 2019 bullpen, it’s the right move long term. I’m serious; McKenzie has the potential to be that good as a starter. If they wisely balk at such an offer, then I’m asking for multiple prospects, starting with RHP Ethan Hankins – a compensatory first round pick in last year’s draft – and OF Will Benson, a 2016 first-rounder whose minor league stats look ugly, but may still possess the highest upside of any prospect in the Indians system. If Chernoff isn’t willing to overpay for Barnes’s services, then there’s no need to move him. However, I’m thinking the Indians will ultimately make a lopsided move in preparation for one more postseason run before the rest of the AL Central catches up with them.

Again, I’m going to recap this entire piece by once more stating that this is an exercise in futility. The 2019 Boston Red Sox will win at least 90 games and make the postseason for the fourth straight year. Honestly, I’m hoping that this article is so obnoxious in premise that it will jinx our ugly start and spark a historic run to a second straight title. If nothing else, it was fun pretending to be Dave Dombrowski in an alternate universe and scouting other organizations’ farm systems for a few hours. Feel free to include your ideas, feedback, or criticisms in the comments section below.

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  1. May 24, 2019

    […] when the sky was falling, and some people actually thought Chris Sale was broken beyond repair – I wrote an article on what the trade deadline would look like if the 2019 Boston Red Sox were sellers. Of course, I […]

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