With the 2019 World Series set to begin, the defending champion Boston Red Sox are less than two weeks away from entering the most tumultuous offseason under the ownership of John Henry in years.

The Red Sox have a laundry list of items to tackle as the offseason is nearly underway. Today, we’ll look a the five priorities the franchise faces as they head into 2020 and beyond…

1. Hiring a new General Manager / President of Baseball Operations:

The unceremonious firing of former Dave Dombrowski sent shockwaves throughout the fan base, the clubhouse, and the rest of Major League Baseball. Dombrowski arrived late in the 2015 season and was tasked with bringing the organization back to its championship status after a dismal season in 2014-2015. “Dealin’ Dave” went to work almost immediately by locking up David Price to a groundbreaking contract. A large move was merely a precursor to what would be followed by a flurry of prospects-for-established player trades that netted Craig Kimbrel, Drew Pomeranz, and Chris Sale. The results? Three consecutive AL East titles (2016-2018), capped off with the franchise’s fourth World Series title since 2004, in 2018. 

Those moves came with a price. The volume and talent of prospects given up to acquire (arguably) the games best closer (Kimbrel) and left-handed starting pitcher (Sale), an All-Star starting pitcher in Pomeranz, along with a  handful of smaller trade acquisitions (Tyler Thornburg, Ian Kinsler, Nate Eovaldi), considerably thinned one of the game’s elite talent pipelines. Thus the Red Sox would enter the 2019 season with a farm system ranked dead last by Baseball America, with no blue chip prospects on the horizon. On top of the depleted farm system, massive contracts and extensions to David Price, J.D. Martinez, Chris Sale, Nate Eovaldi, and Xander Bogaerts, combined with record breaking arbitration raises to 2018 MVP, Mookie Betts, have saddled the Red Sox with the game’s highest payroll, and sizable luxury tax bills in each of the last two seasons. While Dombrowski accomplished what he was brought in to do, his recognition of the organization as a large market, high revenue franchise, and his “win at all costs” mentality, clearly represented a difference of philosophy with ownership, and ultimately led to his dismissal less than a year after building a roster that won a World Series.

John Henry’s lack of patience, and quite possibly unattainable financial goals for the franchise, have surely been noticed across the landscape of MLB, and finding the next GM for what was once considered to be among the best jobs in baseball, may prove to be difficult. Established general managers – Theo Epstien, Mike Hazen, Billy Beane, and Andrew Friedman- have all publicly expressed their intention to stay in their current positions with their current organizations. After taking the “old school” approach with Dombrowski, the Red Sox will explore an organizational shift, and target a GM geared more toward analytics with an eye on keeping the payroll at a manageable number. Whether or not that person currently resides within the organization, or they are able to poach one from another team, the roe needs to be filled sooner than later, as stability in the role will likely be the key to accomplishing the goals attached to the upcoming off season. One name to keep an eye on: Chaim Bloom.

2. Deciding the Long Term Future of Mookie Betts:

The reigning AL MVP has one year of team control left, so theoretically, the team could allow the situation to play itself out while addressing other priorities; however the Betts situation has already become a distraction. While Betts has expressed his intention of testing the free agent market after 2020, it’s more likely a leverage tactic with a message to the organization: “come strong or don’t come at all”. Let’s face it, contracts and salaries in MLB aren’t trending downward, and after an offseason that saw inferior players like Bryce Harper, and Manny Machado sign for 10 or more years at $300M+, that bar has been set for Mookie to surpass, and based on his career trajectory, he’ll like clear that bar by a substantial margin. Ownership may be reluctant to break the bank on Betts, not because he’s not worth it, but because mega-contracts to David Price and Chris Sale, along with lesser deals to Eovaldi and Dustin Pedroia, haven’t produced the return on investment that come anywhere near to the checks that are being written. As a result, the team has the highest payroll in the game, and has paid heavily into luxury tax the past two seasons. With even loftier penalties (50% on every dollar over the CBT line) for surpassing the line in a third consecutive season, the desire to get under the CBT line for 2020 feels like an indirect message to the fans, media, and Betts, that signing him long term may not be in the cards.

While the contracts for Price and Sale provide a cautionary tale for the organization to fall back on should they choose to move on from Betts, lucrative deals for pitchers nearing the age of 30 always come with an assumed level of risk. In the case of Betts, a 27 year old, perennial MVP candidate, on the front end of his prime, the production will likely justify the dollars throughout the majority of the contract. Watching Mookie Betts fall on the sword for irresponsible spending in the past will be a hard pill for the fan base to swallow, trading him in the coming months is a realistic possibility, should organization and player fail to agree to terms to keep him in a Sox uniform for years to come. Recent reports have the organization seeking a young, cost-controlled outfielder that can slot into the 2020 lineup, a mid-rotation starter, and two Top-100 level prospects. Getting back a package like that would be an unprecedented haul for 1 year (at nearly $30M) of a player with no guarantee that he resigns with the acquiring team. Teams like the Dodgers, Braves, Cardinals, Padres, and Giants have all been rumored to as possible matches in a trade for Betts, and each of those organizations could probably convince themselves that a one year run with Mookie may be worth the price tag. While the list of teams that could trade for Betts is limited, the bidding war for his services should prove interesting if he’s ultimately made available.

Another option, should the team fail to agree to terms on an extension with Betts, would be to trade him at the 2020 deadline. At that point, new contenders will likely have emerged, and the temptation to get the team to championship level could present a better package than the ones offered in the off season. The Yankees were able to land uber-prospect Gleyber Torres, in exchange for two months of Aroldis Chapman. The deal became even better for New York when the signed Chapman to a free agent contract after the season, a(n) (unlikely) scenario that Boston could find themselves in.

The best case scenario would be for the organization to find a way to keep and extend Betts. Ultimately realizing that having another decade plus, of their homegrown, drafted and developed, superstar is more of a sure thing than the upside of any prospect package that comes back in return. The new general manager with their work cut out for them from the very first day of taking the job. Hopefully, the future of Mookie Betts is decided quickly, bacause a distraction of that magnitude isn’t how they’d like to start the 2020 season.

3. Waiting on a Potential J.D. Martinez Opt Out

Admittedly, the team has no control over Martinez’s decision to play out 2020 at $23.75M, or if he chooses to exercise the opt-out provision in his contract and head back into the free agent market. What they do have control over is whether they choose to engage him in new contact negotiations should he choose to do so. Usually, an opt-out clause like the one in Martinez’s contract is used a leverage to get the team to add additional years and money to the current deal, but with organization already stating a desire to get under the $208M CBT line, opting out of the deal likely spells the end of Martinez’s tenure in Boston.

J.D. has been as advertised since arriving in Boston in 2018. He’s arguably the best right handed hitter in the game, hitting for a high average, getting on base, driving in runs, and hitting for power. However, at age 32, and with limited defensive value, the Sox could deploy the money freed-up from Martinez to extend Betts, or Rafael Devers should Betts stick to his stance of testing free agency. They could also use the money to shore up a starting rotation that will have some health related concerns, as well as a hole left at the back of the rotation by the departing Rick Porcello. Any of these moves could become realistic possibilities while keeping the goal of getting under the CBT within reach. J.D. Martinez seems to not only control his own destiny, but the destiny of several players should he choose to opt-out.

4. Fixing the Starting Rotation:

What was looked at as a strength heading into 2019 quickly became the teams Achilles heel. The Chris Sale extension (5 yrs / $150M) was seemingly met with serious concern before the ink was barely dry. All of the good feelings and nostalgia that Eovaldi brought into the season coming off a brilliant 2018 postseason were quickly dissolved after a dismal start to the season that saw him going under the knife (again) less than a month into the 2019 campaign. The hard throwing righty would make his way back, only to finish the season with an ERA over 6.00. David Price, owner of the largest free agent contract for a starting pitcher in MLB history, would finish the season on the DL, after putting up the most inconsistent numbers of his career. Former Cy Young award winner, Rick Porcello, would remain healthy throughout the season, but ultimately have the worst year of his career and rank among the bottom of starters in all of baseball in overall efficiency. Only Eduardo Rodriguez (19-6 3.83 ERA) would prove to be a consistent, stabilizing presence in the rotation. Injury forced Brian Johnson, Hector Velazquez, Ryan Weber, and Andrew Cashner  into the rotation at various points in the season, but none proved capable of handling the responsibility. Likewise, prospect, Mike Shawaryn, Travis Lakins, and Darwinzon Hernandez proved not-yet-ready to take on the responsibility of holding a spot in the starting rotation.

With lingering concerns surrounding the health of Sale, Price, and Eovaldi, and the departure of Porcello, starting pitching would seem to be high on the priority list of roster additions heading into 2020. With noted payroll limitations and luxury tax ramifications, marquee free agents like Gerritt Cole and Stephen Strasburg are unlikely to be pursued, especially after seeing the results of Price and Sale, the last two pitchers the franchise invested $30M+ per season into. The next tier of free agent pitchers – Hyun-Jin Ryu, Zack Wheeler, Madison Bumgarner, and Jake Odorizzi- would each draw some level of interest from the Red Sox, but the aforementioned payroll limitations would likely exclude the Sox from any type of bidding war for their services. The third tier of free agent starters is likely where Boston will find themselves once free agency begins. Pitchers such as Cole Hamels, Kyle Gibson, Tanner Roark, Julio Teheran, and Wade Miley could all fit the bill of veteran, back end starter, capable of eating innings while still presenting some upside. With a desire to get under the $208M CBT line, short-term deals with with AAV’s in the $10M range or less are what the team will be targeting. Even with starting pitching being at a premium, one or more of these pitchers should be within reach for the organization.

5. Solidifying the Coaching Staff

With all of the uncertainty headed into the off season, one of the things we know to be certain is that manager, Alex Cora, will be in the dugout to start the 2020 season. Much of the rest of his coaching staff is still up in the air. Immediately after the regular season ended, pitching coach, Dana Levangie, was relieved of his duties and reassigned within the organization as a scout. Assistant pitching coach, Brian Bannister, and assistant hitting coach, Andy Barrett, were also dismissed. while Cora should have some say as to who joins him on the coaching staff, the incoming general manager will likely want to put some of his own recommendations as the staff as well. With a starting rotation doomed by injury and inconsistency, and a bullpen that led the league in blown saves, Levangie didn’t stand much of chance to come back in 2020. The firing of Dombrowski likely sealed his fate. A fresh voice and new methods will be welcome to a pitching staff with overall underachieving results in 2019.

The offense was among the best in baseball, and steady performances from Betts and Martinez, combined with career years from Xander Bogaerts, Rafael Devers, and Christian Vazquez resulted in Red Sox players being found all over the leaderboards in most offensive categories. However, the Red Sox were a dismal team with runners in scoring position, and finished last in the American League in leaving runners on base. Primary hitting coach, Tim Hyers, will stick around for 2020. 

All of these five priorities, with the exception of the coaching staff, seemed to be tied to ownership’s goal of reducing payroll and staying under the $208M CBT threshold. Accomplishing that goal while remaining in contention may prove to be impossible. All of it should make for an off season that has has the Boston Red Sox dominating the headlines in Major League Baseball.