Even though the World Series champion has yet to be crowned, the Boston Red Sox are knee-deep in the offseason.

Before the final game of the 2019 season ended, the talk around the franchise was focused on the upcoming offseason and the concerns tied to the game’s highest payroll and the escalating luxury tax penalties that come with passing the threshold in multiple seasons. Rumors have been swirling in regard to franchise player, and former MVP, Mookie Betts, who enters his last season under team control before hitting the free agent market. If the team is unable to come to terms on a contract extension with Betts, he’ll play the 2020 season with an arbitration salary projected around $28M. Mookie will be joined in arbitration by eleven other players, highlighted by Jackie Bradley (projected $11M), Eduardo Rodriguez ($9.5M), Andrew Benintendi ($4.9M), and Brandon Workman ($3.4M). While the team has some money coming off of the books, most notably dead weight contracts owed to Pablo Sandoval and Hanley Ramirez, and current expiring deals to Mitch Moreland and Steve Pearce, freshly signed extensions for Xander Bogaerts ($20M/Season), and Chris Sale ($30M/season) will go into effect starting in 2020, and the aforementioned arbitration raises will bring the payroll to nearly $200M before adding a single player. 

Factoring into the payroll is the near $23M in 2020 owed to All-Star designated hitter, J.D. Martinez, who holds a player opt-out in his deal that could that could save the franchise a sizable amount should he choose to exercise the provision in his contract. Martinez has proven to be worth every dollar of his contract, but with limited defensive value, the Sox could find an adequate replacement on the free agent market for much less than the amount owed to Martinez. The team could also explore trades for Bradley, who’s offensive limitations have frustrated the organization for years, but at 1 year and a projected $11M in salary could bring back a decent prospect from a team in need of everyday outfield help, and Betts, who’s expressed his desire to test the free agent market after 2020, and would bring back an unprecedented haul of young talent for a player with only one year of team control remaining. While those types of trades would solve some short-term payroll issues, and draw the ire of fans- especially in the case of Betts- the (now) ill-advised contracts of David Price ($33M/season), Nate Eovaldi ($18M /season), Dustin Pedroia ($15M/season), and Sale ($30M/season), combined with future escalating arbitration raises to key players, will likely have the team facing a similar payroll crunch regardless of how much they’re able reduce heading into 2020. 

One way to get out in front of the future payroll situation would be to extend key young players now, avoiding the annual arbitration increases, and providing long term security to these players ahead of unrestricted free agency where a bidding war could seriously hinder the Red Sox from retaining them. Today we’ll look at several extension candidates and what those extensions might look like…


1. Rafael Devers:

The soon to be 23 year old third baseman had a breakout season in 2019, and his name can be found near the top of the leaderboard in nearly every major offensive category. With four years of team control left, and not being arbitration eligible until after the 2020 season, now would be the time to get Devers signed long-term. He’ll play 2020 at a renewed contract rate around $700k, but will likely follow a similar path of Mookie Betts once he becomes arbitration eligible, with projected salaries around $10M in year one, $20M in year two, and upwards of $30M in his final year before hitting the open market. The Atlanta Braves signed young star, Ronald Acuna Jr. to an 8 year/$100M extension prior to the 2019 season, and the organization will likely look at that model as a starting point on the Devers extension. But that contract was universally looked at as one of the more “team friendly” contracts in the sport upon it’s announcement, and Acuna’s rise into superstardom in 2019 now make it arguably the best deal in all of the sport from an ownership standpoint.

More likely, the extension given to Astros third baseman, Alex Bregaman, will serve as the model to extend Devers. Bregman came into 2019 with nearly the same amount of service time that Devers will have going into the 2020 season, and while Bregman is nearly three years older than Devers, his defensive value as a premium third baseman, and and above average shortstop (when needed), bring more value overall to a player with similar offensive stats and upside to Devers. Bregman’s contract extension called for him to play the 2019 season at a renewed amount of $640.5k, before receiving $13M per season in each of the following 3 seasons (effectively buying out the arbitration years), and $30M per season in 2023, and 2024. The deal essentially saved the Astros in the neighborhood of $40M in total contract value based on projected arbitration increases and free agent value for 2023 and 2024. The Red Sox will likely use some type of middle ground between the Acuna and Bregman deals when presenting an extension for Devers. 6 years and $100M seems like a reasonable offer for both sides, with a similar structure to the Bregman deal- $700k for 2020, $12.5M 2021-2023, and $21M per season from 2024-2026. If Devers is able to remain consistent in his offensive production through the duration of that contract, he’ll enter free agency at age 29, with an opportunity cash in on a second contract in excess of $100M.

2. Eduardo Rodriguez:

He’s not an ace, but after a 2019 that saw Eddie post a 19-6 record with a 3.81 ERA and 213 K’s in 203 IP, he is a solid front rotation starter. The ability to slot in that type of production behind a healthy Chris Sale and in front of (hopefully) a healthy and consistent David Price and Nate Eovaldi could make the Red Sox starting rotation one of the best in the American League. With a projected arbitration increase of $9.5M for 2020, and upward of $15M for 2021, the Sox should start to plan for the departures of Price and Evoldi when their current contracts expire after the 2022 season. Recent examples of pre-arbitration deals for Blake Snell (5/$50M), and Luis Severino ($4/40M) place young, front-end starters at roughly $10M per season, but ERod will get nearly that in his upcoming go thru arbitration, and he’ll certainly surpass that amount with a similar campaign in 2020. A five year/$65M deal for Rodriguez would give him an average of annual value of $13M per season, and some long-term security should his numbers in 2019 prove to be an outlier.

3. Andrew Benintendi:

The 2015 first round pick has been solid since taking over the starting left field spot in late 2016, but has yet to take the next step in his game. “Benni”has failed to live up to the hype and pedigree that come with being the seventh overall pick in the draft and the Golden Spikes award winner. He’s been an everyday starter and has remained relatively healthy. He’s coming off his worst season, batting .266 with 13HR and a .774 OPS, while accumulating a career low 1.7 WAR. That said, He’s shown the potential to be more than a solid regular, and scouts and evaluators believe there is some upside remaining in his game. Taking a look at a similar player comp to Benintendi at this stage of his career, it’s easy to point to the Miami Marlins and the extension given to now reigning NL MVP. Christian Yelich. Yelich agreed to a 7 year/$49M extension prior to the 2015 season, buying out his arbitration years at $1M, $3.5M, and $7M, before seeing the final four years of his deal gradually increase his annual salary from $9.75M in 2019, to $15M in 2022. The Marlins were early to the negotiation table with Yelich, and gambled on his upside with sizable pay increases each year until the deal expired in 2022. Prior to the extension, Yelich had never had an OPS over .782, but had won a Gold Glove award. Of course, Yelich has now blossomed into one of the premier overall hitters in the game, his contact skills, power, speed, and defense have him in line to finish in the top 3 in MVP voting for a second consecutive year, and his contract represents the best value in all of baseball.

The Sox could take a similar gamble on Benintendi’s upside, but because he’s entering his first year of arbitration and is projected to earn just shy of $5M, the overall deal is likely to be larger than the Yelich extension. 5 years/$60M would allow the Sox to buy out Benintendi’s arbitration years and control two years beyond that at an AAV of $12M per season. If Benintendi discovers a career resurgence anywhere near what Yelich has become than Sox will have inked one of the best deals in the game. If Benintendi only experiences an uptick in production and taps into 20+ home run power, while producing an OPS north of the .800, and continues to play above average defense, the contract will still be looked at as below market value.

4. Brandon Workman:

Finding a reliable closer is hard. The Red Sox chose to move on from perennial All Star, Craig Kimbrel, and logical replacement, Joe Kelly, after the 2018 season. That decision drew plenty of criticism at the time, but after terrible seasons from both, it looks to have been a smart move. The fact is, the closer market is volatile, and shelling out top dollar in the free agent market can be crippling for a team with payroll issues. Recent deals for Wade Davis, Kenley Jansen, Mark Melancon, and Kimbrel himself have proven to disasters. Trading for an elite closer can also be futile, as the Mets gave up their top two prospects and took on a bad contract in Robinson Cano to acquire Edwin Diaz. Diaz would finish his first year in Queens with a 5.59 ERA and just 26 saves in 66 appearances. In Workman, the Red Sox may have found a reliable ninth inning stopper, as evidenced by his 10-1 record, 1.88 ERA, and 16 saves. He was used in high leverage, late inning spots before assuming the closer role on a permanent basis in mid-August. He would be named the AL reliever of the month in September. Workman isn’t exactly young (he’ll be 31 on Opening Day), and he doesn’t have a lengthy track record in the ninth inning, but a mid-90’s fastball and a devastating curve ball give him a premium two-pitch mix to close out games. Workman is headed into arbitration for the second time this off season and is projected to earn $3.4M. Boston would be wise to explore a 5 year/$30M extension, with the hope that the closer role won’t be a worry for the next half decade.

5. Mookie Betts:

Yes, Mookie should be #1 on this list. His future with the franchise will certainly be the #1 priority this off season. However, agreeing to terms on an extension – no matter how lucrative – is no guarantee. He’s earned a total of $30M through his first two trips in arbitration and is is projected to be in the neighborhood of $28M should he choose that route again. Betts turned down an 8 year/$200M extension after the 2017 season, and since that point has won a Wold Series, and MVP, and has established himself as an elite, Top 5 player in all of the sport. In that time he’s seen inferior players, Bryce Harper (13 years/$300M), and Manny Machado (10/$300M) sign decade long plus deals at staggering annual values. Mookie’s patience and diligence are going to likely earn him a record-breaking payday. Are the Red Sox, a large market team with among the highest revenues in MLB, really going to let a homegrown, drafted and developed, superstar leave the franchise because of bad contracts given out to other players? Maybe…probably. It would seem that a roster domino effect would have to go into place for the team to truly go all in on the type of extension that would prevent Mookie from exploring free agency. If Martinez opts-out, and a trade for Bradley can materialize, the Sox may be able to get under the CBT line for 2020 and avoid the harshest of penalties, allowing them to spend a little more loosely in the seasons immediately after.

All told, the organization may get just one shot at extending Betts before he becomes available to the rest of league, so the offer is going to have to be a strong one. Betts will likely command at least a decade in contract length, and an AAV in the mid-$30M range. Even if additional money becomes available with the Martinez opt-out and an additional trade or two, the Sox may have to toss the goal of staying under the $208M CBT line out the window. But Betts age (26) and resume (MVP, World Series champ, four top 6 MVP finishes, multiple Gold Gloves, Silver Sluggers, and All Star appearances…) have him in line to cash in on the richest contract in the history of the sport, and for an ownership group that’s spent recklessly for nearly two decades, tightening the purse strings when the greatest homegrown player in the history of their tenure is about to become a free agent sends a bad message to a rabid, passionate fan base. 10 years and $350M ($35M AAV) or 12 years at $400M ($33.3M AAV), maybe with an player opt-out in the middle of the deal, should be enough to convince him from testing free agency. If he still chooses to so, it’s the type of offer that can justify the decision to trade him to the fans and media.

While extending all of these players in this upcoming off season is unlikely, the team should sit down with each of these players and their representation to see what it would take to them in a Red Sox uniform for years to come.