Red Sox Can Avoid, Mitigate Inevitable Rebuild with Smart Moves

2018 saw the Boston Red Sox claim the World Series title for the fourth time since the turn of the millennium, and with the bulk of the team sticking around in Beantown, it seems as though they will be just as competitive again in 2019. That said, there are some factors that are already to begin working against the Red Sox. For one, the continued improvement of the division rivals in New York and Tampa Bay makes a division that featured three 90-win teams in 2018 even stronger. Meanwhile, the Sox have not had a great offseason to date, as they have already lost Joe Kelly to the Dodgers and seem just as likely to lose Craig Kimbrel to free agency as well. Here is a breakdown of Boston’s offseason to this point:

According to, Boston has a projected 2019 salary of $225.0425 million which remains well above the luxury tax. While the Sox are a wealthy organization, this staggering figure surely poses a legitimate obstacle in attempting to bring in further upgrades. This figure doesn’t improve very much in coming seasons, as they have $104.3 million already guaranteed on the books for 2020, $88.725 million for 2021 and $77.35 million. This doesn’t even take into account arbitration raises, which should be rather significant for players such as Mookie Betts, Andrew Benintendi, and Eduardo Rodriguez.

With limited payroll space to work with over the next four to five seasons, Boston will need to get creative with how to continue to try to field a 25-man roster. Unfortunately, to make matters even more difficult, they have one of the worst farm systems in the entire major leagues.

With all of this in mind, the Sox could be looking down the barrel of a potentially lengthy rebuild in the coming years, but it’s not too late to right the ship and make it run more efficiently.

Plan of Attack Through 2019

As it stands, the Red Sox are set to lose a quintet of rather solid free agents following the 2019 season:

Obviously this will hurt. None of these guys are on contracts considered to be “albatrosses” with Porcello being the only one crossing the $20 million annual figure for 2019. If I’m the Red Sox front office, I’m looking at this group, and figuring out how to minimize the loss, without handicapping the organization in the long run.

The Boston @RedSox can be competitive for awhile, but a rebuild is inevitable. The team can mitigate their eventual rebuild with some intelligent front office moves going forward, writes @OrsattiJoe.Click To Tweet

As a contending team, it makes no sense to trade off legitimate major league assets for prospects, so the question becomes: which of these guys deserve qualifying offers, who could the team live without and how can the team replace them without breaking the bank.

I saw two obvious qualifying offer candidates: Chris Sale and Xander Bogaerts. I considered Porcello to be a borderline candidate. While his tenure with the Red Sox included an excellent 2016 season, the other three years have been exceptionally underwhelming. Furthermore, going by Baseball-Reference, in his Cy-Young winning season, his bWAR ranked 8th, his ERA ranked 8th (sixth among starters) and his ERA+ ranked 5th (3rd among starters) among AL pitchers who received votes during that season.

While Porcello would probably decline the qualifying offer, netting the Sox a compensation pick, I believe that if they traded him during the offseason, they could get more for him than the compensation pick. Furthermore, I think there are better options that can replace Porcello for a lot less money. The way that I would proceed would be to wait out the Madison Bumgarner and Corey Kluber markets. As it currently stands, there are a litany of teams in need of front end rotation help: Milwaukee, Both LA teams, Philly and Atlanta all represent possible landing spots. With five teams in search of front line rotation help, that leaves two left after trades of MadBum and Kluber (or Bauer) and the signing of Dallas Keuchel. At this point, you have a lot of leverage for the following reasons:

  • You are not just selling Porcello, but also the compensation pick assuming he declines a qualifying offer.
  • With two teams looking to make major splashes in the rotation, they may be willing to pay out more to acquire it. Furthermore with the prior deals having already been completed you can use them as a baseline.
  • At the end of the day, you don’t need to make the trade. If the offers aren’t enticing enough, then you still have the QO to fall back on. This could cause for the quality of the offers to be higher, as teams would be aware of this fact.

In any trade for Porcello, I would say that the Red Sox must insist on acquiring a controllable major league arm and a young starting pitching prospect as well as a sweetener or two. I feel like the Dodgers are in the best position to make a trade with the Red Sox as they have a surplus of major league depth with no place on their major league roster and a desire to upgrade an already outstanding rotation.  While it’s pure speculation, I’m thinking a return of Ross Stripling, Brock Stewart, Dennis Santana and a low-level lottery ticket.

Figure Stripling is a legitimate major-league starter without a spot in Los Angeles, Dennis Santana looks like a future two or three, and Brock Stewart is a decent pitcher who could have been cut loose by Los Angeles anyway. All of Stripling’s peripherals suggest that his success should continue when given opportunities, Santana is a B-level prospect who has high upside and looks to be almost major league ready while Brock Stewart has been dominant in the Triple-A Pacific Coast League, and simply hasn’t been given many opportunities for the Dodgers.

Looking at the remaining four impending free agents, only Brock Holt seems likely to have a noteworthy market, as the first base market has been horrible over the past few offseasons and there are more inexpensive options available, while Nunez’s stock is as low as it’s been in a while. Holt, on the other hand, is coming off of a rather successful 1.1 bWAR, 1.4 fWAR season and is among the more versatile players in the league. A good reference point of potential return would be to consider Holt’s value between that of Aledmys Diaz (who brought back Trent Thornton) and Tommy La Stella (who brought back Conor Lillis-White). In an attempt to give some perspective on what kind of player it would be, I’m going to use the Seattle Mariners as a viable trade partner based on the fact that Jerry Dipoto is very interested in versatility, and their super utility guy is Kristopher Negron.

I would consider a C+ prospect such as Robert Whalen or Max Povse to be a reasonable expectation for a return. Now, you may be thinking, “Why would the Red Sox trade an important bench guy like Brock Holt, and how does it make the team better?.” First of all, we’re looking at nearly $6 million saved and a young pitcher who could be used in the major-league rotation this season. Secondly, the Red Sox have a replacement who could very well serve as an improvement over Holt already on the 40-man roster. 26-year-old Marco Hernandez has been forgotten about by many after missing the 2018 season to injury, but t should be remembered that he has posted a strong career batting line of .284/.328/.349 over 116 plate appearances. He is also a left-handed hitter, which keeps the balance of the projected Red Sox bench, and has been known to play the middle infield well above average while playing a decent third base. The best part about him is that he is under team control through 2022.

With the money they saved, they can go after a bullpen guy. As it stands, Brian Johnson represents the only left-handed relief option projected to break camp with the club with Bobby Poyner on the taxi-squad. While it doesn’t make sense to go and trade for an overpaid closer type, there are three free agent options who will be exceptionally inexpensive despite consistently posting strong results: Dan Jennings, Xavier Cedeno and Jake Diekman.  Grab one of those guys on an inexpensive two-year guarantee (see Jared Hughes contract) and have them serve in a set-up capacity. With two years on the deal, it gives you more security and more time to build your own great reliever.

Hypothetically, going into 2019, the Sox now have a rotation of Sale, Rodriguez, Nathan Eovaldi, David Price and Ross Stripling and a bullpen of Ryan Braiser, (Diekman/Cedeno/Jennings), Matt Barnes, Heath Hembree, Tyler Thornburg, Brian Johnson and Brock Stewart with Hector Velazquez, Bobby Poyner and Colten Brewer representing the most viable taxi options.

As for Moreland, Pearce and Nunez, it wouldn’t make sense to trade them at this time, as their value to the team surpasses the return. That being said, if one or more of Sam Travis, Josh Ockimey and/or Michael Chavis find success this season, either of the inexpensive impending free agents could become mid-season chips that could be flipped to acquire more controllable talent while saving money and giving at bats to one of the younger guys who could become a longer term piece.

So essentially, what this does is it gives the Red Sox some pieces to minimize the loss of Chris Sale and Rick Porcello to an extent while giving them a pair of compensation picks in the 2020 draft. Before making any acquisitions in the 2019-20 offseason, the Red Sox would have a projected rotation of David Price, Eduardo Rodriguez, Nathan Eovaldi and Ross Stripling with Brock Stewart, Tanner Houck and Mike Shawaryn representing legitimate, high upside options for the fifth spot, a solid controllable bullpen and one obvious need: shortstop.  As the season progresses the market will become a bit clearer. At this point, I would consider Jackie Bradley Jr. as a flip candidate.

While it might seem like an insane course of action, at their current trajectory, the Red Sox will wind up with an old, expensive roster limiting flexibility by the middle of the upcoming decade. These steps keep them competitive while improving their long-term outlook.

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