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Newly-hired chief baseball officer Chaim Bloom faces an immediate challenge in getting the Red Sox back to the postseason while simultaneously navigating a difficult payroll situation.

Guaranteed Contracts

• Chris Sale, SP: $145MM through 2024
• Xander Bogaerts, SS: $120MM through 2025 (plus $20MM vesting option for 2026)
• David Price, SP: $96MM through 2022
• J.D. Martinez, OF/DH: $62.5MM through 2022 (2021-22 seasons could become mutual options if Martinez suffers Lisfranc or related injuries to his right foot)
• Nathan Eovaldi, SP: $51MM through 2022
• Dustin Pedroia, 2B: $25MM through 2021
• Rusney Castillo, OF: $13.5MM through 2020
• Christian Vazquez, C: $10.7MM through 2021 (includes $250K buyout of $7MM club option for 2022)

Arbitration-Eligible Players (projections via Matt Swartz)

• Jackie Bradley Jr. – $11MM
• Sandy Leon – $2.8MM
• Mookie Betts – $27.7MM
• Brandon Workman – $3.4MM
• Eduardo Rodriguez – $9.5MM
• Matt Barnes – $3.0MM
• Heath Hembree – $1.6MM
• Andrew Benintendi – $4.9MM
• Marco Hernandez – $700K
• Josh Osich – $1.0MM
• Non-tender candidates: Hernandez, Leon, Osich

Free Agents

• Rick Porcello, Mitch Moreland, Brock Holt, Andrew Cashner, Steve Pearce, Eduardo Nunez, Tyler Thornburg, Jhoulys Chacin, Steven Wright, Gorkys Hernandez, Chris Owings, Juan Centeno, Josh Smith

After 15 seasons in the Rays’ front office, Bloom is no stranger to the difficulties of trying to manage a payroll while also trying to keep a competitive team on the field.  It’s just that now, Bloom will be dealing with a payroll more than three times as larger than anything he ever dealt with in Tampa Bay — not to mention exponentially more pressure from fans, media, and his own bosses.  As evidenced with predecessors Ben Cherington and Dave Dombrowski, not even a recent World Series victory can save the head of a Red Sox front office if team ownership isn’t satisfied with immediate results.

As of late September, the organization’s plan was to get under the $208MM Competitive Balance Bax threshold, though Red Sox CEO Sam Kennedy somewhat walked that back by stating that avoiding the luxury tax was a “goal but not a mandate.”  The Sox have exceeded the CBT threshold in each of the last two seasons, and thus as a three-time repeater would face a 50 percent tax on every dollar spent over the $208MM line in 2020, plus an added 12.5% surtax if their luxury payroll falls within the $228-$248MM range.

As currently comprised, the Red Sox have a luxury tax number of just over $236.3MM (as per Roster Resource) for next season.  Ducking under the $228MM mark seems feasible.  However, it would take some judicious cutting and/or creative trades to slide under the $208MM threshold and reset Boston’s tax penalties entirely, given the number of needs on the roster.

Obligatory reminder: the luxury tax is not an exorbitantly punitive sum.  Exceeding the top level of the luxury tax in 2018 cost the Red Sox roughly $11.95MM (and a ten-slot drop in their 2019 draft order), and their 2019 tax penalty will be in the neighborhood of $13.05MM, as per Ronald Blum of the Associated Press, with no change to their draft position.  Every organization has a budget, and it’s understandable that Red Sox ownership is less willing to pay tax penalties for an 84-win team than it was for a World Series champion, but there isn’t any concrete reason why Boston (or any big-market team) should be treating the CBT as an actual salary cap.  There is surely no small amount of annoyance within the MLBPA and the player agent community that another large-market franchise is seemingly more focused on trimming payroll instead of spending.

It’s also worth noting that Boston’s payroll situation would be a lot clearer if ownership hadn’t given Dombrowski the green light to re-sign Nathan Eovaldi in free agency last winter or to give Chris Sale a five-year extension that begins in 2020.  Those two contracts, plus the $96MM still owed to David Price, now all loom large as question marks after all three pitchers battled injuries last season.  Some level of a rebound is certainly possible, but it’s unlikely that all three will be healthy and pitch up to peak standards next year, leaving the Red Sox without much flexibility for rotation upgrades.  Eduardo Rodriguez has a checkered injury history of his own, but the southpaw was a bright spot last season, posting a 3.81 ERA over a career-high 203 1/3 innings.

For the remaining rotation spot, the Sox could look to sign any number of low-cost veterans, and maybe even reunite with Rick Porcello.  Or, since the Red Sox already began using openers last season, the club could instead deploy a full-time opener/bulk pitcher combo in the fifth starter position rather than a proper starting pitcher.  Given that Bloom was one of the architects of the opener strategy in Tampa Bay, this might be a more likely (and cost-effective) route for the Sox to take rather than spend a few extra million on an innings-eating starter.  It might not even be out of the question for the team to explore putting an opener in front of Eovaldi, if injuries continue to be a factor.

A deep bullpen is a necessity for a team using an opener, and the relief corps is another area of need.  Brandon Workman’s role will be of interest, as the veteran righty emerged as Boston’s closer down the stretch and posted an impressive 1.88 ERA and 13.1 K/9 over 71 2/3 innings.  There was some volatility in those numbers, as Workman (like virtually every Sox reliever in 2019) had control issues (5.7 BB/9).

The Red Sox could prefer to use Workman in a setup role rather than as a closer, or at least acquire another arm who has ninth-inning experience as depth to work behind Workman.  Sergio Romo is a known quantity to Bloom from his time in Tampa, and Romo would also come at a much lower price than other top relievers on the market; a play for Will Smith seems out of the question, and Boston’s spending concerns could possibly even keep them out of the Will Harris/Drew Pomeranz tier.  Names like Chris Martin, Craig Stammen, or Daniel Hudson could all be considered, as could a pursuit of a bounce-back candidate Dellin Betances.

Turning to position players, one of the team’s biggest offseason questions has already been answered, as J.D. Martinez decided not to opt out of the remaining three years of his contract.  An opt-out would’ve taken $22MM in average annual salary off of Boston’s books and given them more tax breathing room, though it would’ve come at the cost of one of the game’s best sluggers.

Instead, Martinez will now rejoin Mookie Betts, Xander Bogaerts, and Rafael Devers in one of the sport’s most fearsome lineup quartets.  Catcher Christian Vazquez enjoyed the best hitting season of his career, though the Sox will be looking for more from Andrew Benintendi in 2020 after the outfielder scuffled through a down year.

With Mitch Moreland and Brock Holt headed for free agency, and Dustin Pedroia’s playing future still unclear, both first base and second base are up for grabs.  Michael Chavis had a solid rookie year and is a candidate for regular playing time at either position.  Top prospect Bobby Dalbec could work his way into the first base conversation as early as next season.  A left-handed bat would be the ideal complement to the right-handed hitting Chavis and Dalbec, and for both bat-sided and versatility reasons, re-signing Holt (or a Holt type like Eric Sogard) would make a lot of sense.  Bringing Moreland back is also possible if the Red Sox are comfortable with Chavis as a second baseman, but the team will have plenty of options to consider on the crowded first base/DH market.

The Red Sox have already cut down on their projected arbitration costs by parting ways with Steven Wright, Gorkys Hernandez, and Chris Owings, while also adding lefty Josh Osich to the list after claiming him from the White Sox.  That results in a projected savings of $4.5MM, and a bit more money could be saved if the Sox non-tendered Sandy Leon or Marco Hernandez.  As much as the Sox prize Leon’s defense and game-calling abilities, they could see $2.8MM as a high price for a player with no offensive value.

As generally strong as this position player mix looks, there has been a great deal of speculation about whether all of the key players will be back in 2020.  Injuries and contracts make Price, Sale, and Eovaldi difficult to trade — to varying extents.  Unless the Sox take another unfavorable contract back in return, pay down some of the remaining salary and/or attach young talent from their already-thin minor league system to entice a rival team to absorb one of these salaries, they’ll have a difficult time finding a taker.  Therefore, the easiest route to creating payroll space would be to trade a high-salaried position player.

Bogaerts clearly isn’t going anywhere, and Martinez will be able to modify his three-team no-trade list later this month, per MassLive.com’s Chris Cotillo (Twitter link).  Given the lack of win-now teams with a DH opening, that list can be tailored to the current market, thus making a Martinez trade difficult for Boston.  That leaves Betts and Jackie Bradley Jr. as the likeliest candidates to be dealt.  Bradley is projected for an $11MM salary in his final year of arbitration eligibility — a hefty number for a player who has had below-average offensive production for the last three seasons and (of greater concern) also had a drop-off with the glove in 2019, according to the UZR/150 (-1.8) and Defensive Runs Saved (-1).

The Red Sox don’t plan to non-tender Bradley, as they’ll explore trade possibilities in an offseason that doesn’t feature much in the way of interesting free-agent center fielders.  Moving Bradley for a starter, reliever, first baseman, or second baseman would be a canny way of addressing a need if not necessarily saving on payroll, though any number of multi-player arrangements could be explored.  In terms of replacing Bradley, Betts or Benintendi could be moved into center field, with the Sox then acquiring a lower-cost corner outfielder.

And then there’s the possibility of a Betts trade, which would be much more of a game-changer.  Betts is only under contract for one more season, and he has been open about his interest in reaching the free agent market rather than signing an extension with the Red Sox (though he has said he enjoys playing in Boston).  With Martinez and his salary back in the fold, it could increase the chances of Betts being dealt, as painful as it would be to unload one of the game’s best players.

To land Betts, a team would have to be willing to give up a noteworthy combination of big league-ready young talent and prospects for just one season of Betts’ services, and also be capable of absorbing his $27.7MM in projected salary.  In exploring the Betts trade market last month, I listed the Phillies, Reds, Mets, and Padres as perhaps the best candidates since all four teams are aggressively planning to contend in 2020, though it’s possible more clubs could enter the mix depending on how other offseason business plays out.

The Rays swung several creative trades during Bloom’s tenure, so any number of multi-team possibilities could be explored to create a Betts deal that would most benefit the Sox from both a financial and player return standpoint.  One would imagine, however, that Bloom will look into myriad cost-cutting measures before getting around to the Plan C or Plan D that would be a Betts trade.  Kennedy’s comments suggest that the Red Sox could settle for just getting into the lowest tier (spending between $208MM-$228MM) of luxury tax penalties, if avoiding the tax entirely will severely hamper the team’s chances of competing in 2020.

Ownership has made it clear that winning is still the priority, so the Red Sox will try to emulate the Dodgers (led by Andrew Friedman, Bloom’s old boss in Tampa Bay) in escaping luxury tax purgatory while still reaching the postseason on an annual basis.  It will be a tall order, though with all the talent already on the roster, the Sox could only be a few moves — albeit perhaps large moves — away from another playoff berth.