The Red Sox maintain one of the highest payrolls in all of MLB. How will they maintain their core?

The Red Sox have certainly upgraded their roster with Dave Dombrowski at the helm, but that hasn’t come without challenges. J.D. Martinez and David Price represent high monetary commitments under Dombrowski’s reign. Additionally, Hanley Ramirez, Rusney Castillo, and Pablo Sandoval take up cap space from prior poor contracts.

The challenge becomes the escalating luxury tax penalties looming in the near future – including the loss of draft picks and position.

A star-studded free agent class is upon us in the upcoming offseason. The key players in the class, Bryce Harper and Manny Machado, are rumored to be be seeking long term deals worth up to $400M, with average annual salaries close to $40M. The Red Sox own superstar, Mookie Betts, is statistically better than both, and will certainly require a similar contract when he hits the free agent market after the 2020 season. He’ll likely break the record for arbitration contracts the next two season, requiring close to $20M per season, before hitting the free agent market if the Sox are unable to agree to an extension.

JD Martinez’s 5 year / $110M deal signed before the season looks like a bargain right now. His agent, Scott Boras, had floated the idea of a $200M+ deal heading into free agency, and if Martinez continues on the pace he’s been playing he may very well be worth it. Martinez has an opt out in his deal after the 2019 season, and is virtually guaranteed to hit the open market. It’s safe to say that if he does, he’ll be paid like one of the very best hitters in the league, a number substantially bigger than what the Red Sox are paying him now.

Chris Sale is a bona fide ace. He’s arguably the best pitcher in all of baseball when you factor in his performance and his durability. He came to the Red Sox via trade after the 2016 season after signing a team friendly deal with Chicago that bought out his arbitration years. He’s making just $12.5M this season, and will make $13.5M next year, the last year on his deal before coming a free agent. In free agency he’ll likely command a deal north of David Price’s 7 year / $207 million contract.

There is also the impending free agency of all-world closer Craig Kimbrel to deal with at the end of this season. Recent top tier closer Aroldis Chapman and Kenley Jansen signed long team deals with an annual value near $20M per season, and Kimbrel will certainly command a similar deal on the open market. The Sox don’t look to have a “closer in waiting” to replace Kimbrel on the current roster – unless DD trusts Joe Kelly, or recently drafted Durbin Feltman to do the job in the future.

A recent trend around the league is to sign young players to long term extensions buying out arbitration years and securing a few years of addition service, effectively pushing back free agency by two or three seasons. Recent examples are Christian Yelich with the Marlins and earlier this season Paul DeJong signed an extension with the Cardinals.

The Red Sox would be wise to explore this type of situation with Andrew Benintendi, but doing so at this point would likely cost upward of $15M per season. While there are certainly more pressing needs than locking up Benintendi long term at this point, he may end up commanding the biggest contract of the group when he hits free agency after the 2022 season.

Paying the six player mentioned above- not including an extension for Beninteni- along with future salaries due to David Price and Dustin Pedroia will likely cost in excess of $200M per season. It seems like an unrealistic commitment when you have to field a 25 man roster.

Hard decisions are on the horizon. It is very likely that either Jackie Bradley, Xander Bogaerts, Drew Pomeranz, and others may be in their last few seasons as members of the Boston Red Sox.