The Red Sox are no longer reigning World Series champions – it’s time to get back to work.

The Boston Red Sox, just a year removed from celebrating their fourth World Series title since 2004, have a lengthy checklist to address after a 2019 season that saw them finish 20 games out of first, and missing the playoffs for the first time since 2016. With new president of baseball operations, Chaim Bloom, in place, the organization must now focus on superstar right fielder, Mookie Betts, who enters 2020 in his final year of team control, before becoming a free agent. Today, we’ll look at the circumstances surrounding Betts from the organization’s side, as well as the player’s.


The Organization: A History of Making Tough Decisions

Owner, John Henry, has stated that the primary goal headed into 2020 is to reduce payroll with the end result being to get under the $208M CBT line, thus avoiding the harshest penalties for repeat offenders of the maximum luxury tax threshold. With Bloom at the helm, the Sox have a young, analytics-minded leader that comes from a successful, small-market franchise and has experience maximizing a roster while working on a tight budget. The first thought among fans and media upon the announcement of the hiring of Bloom was that having his experience, combined with the financial resources that come with one of the game’s marquee franchises, would give the Red Sox a best of both worlds scenario, where Bloom could identify value relative to the market, and augment a roster that showed some clear signs of decline in the 2019 season. However, with nearly $200M owed to about a dozen players (that figure includes arbitration raises due to key players), there’s not really a viable scenario that allows the franchise add impact players without first slashing payroll.

Heavily factoring into the Red Sox payroll for 2020 is 27-year old, former AL MVP, Mookie Betts. He stands to earn a projected $28M in last trip through arbitration, before becoming a free agent after the 2020 season. Based on recent market trends, factoring age, accolades, and performance, Betts projects to sign a free agent contract of at least ten years in length, with an average annual value (AAV) in the $35M range. For a team who’s primary goal is to shed payroll in an effort to reset the luxury tax line, negotiating what promises to be one of the largest contracts in the history of the sport, presents a situation that may not make both scenarios possible to co-exist together.

The current ownership group, led by John Henry, is no stranger to severing ties with franchise icons. He made the contract negotiations, and subsequent trade efforts, of star shortstop, Nomar Garciaparra, public, and messy following the 2003 season. Nomar would ultimately be moved at the 2004 trade deadline, just a few moths ahead of the franchise’s first World Series win in 86 years. Henry would follow that title with an offseason that saw franchise icon, Pedro Martinez, depart via free agency, joining the New York Mets. He allowed perennial all-star, Manny Ramirez, to publicly question the direction of the team and demand a trade, eventually shipping him to the LA Dodgers in 2008. And after a controversy involving fried chicken and beer in the clubhouse- along with a late season collapse in 2011- history making manager, Terry Francona, and general manager, Theo Epstein, found their way out of Boston. When faced with a payroll crunch in the past, Henry watched as former GM, Ben Cherington, was able to jettison regrettable contracts of Carl Crawford, and Josh Beckett, along with all star first baseman, Adrian Gonzalez, to the Dodgers in 2012, in what amounted to full on salary dump, allowing the organization to free up the money to build a roster that would win the 2013 World Series. That following off season would see the organization let star outfielder, Jacoby Ellsbury, depart via free agency, signing with the rival NY Yankees for 7yrs/$153M. In each of those instances, Henry & Co. came out looking like geniuses. For all of the adoration that fans had for homegrown players Garciaparra and Ellsbury, each had just turned 30 and were coming of prior seasons with major injuries that saw them spend significant time on the DL, and diminished production upon their return from it. Both would go on to have lackluster, injury plagued careers after leaving Boston. The same can be said for Martinez, Ramirez, Crawford, Beckett, and Gonzalez, while the Red Sox went on to win championships in the years following their departures. 


Can John Henry, and by extension, Chaim Bloom, allow the same fate to follow Mookie Betts? It certainly seems like a real possibility. The case of Betts is different in many ways, however. Having just turned 27, and finishing in the top 6 in MVP voting every year starting in 2016, Mookie Betts has established himself as one of the elite all-around players in the game. Unlike the players previously mentioned, Betts has remained healthy throughout his career, and his age places him on the front end of his prime years. While ownership has come out on the right side of the previously mentioned moves, allowing Betts to build upon his already impressive resume, and finish out his Hall of Fame career in another uniform would be a nightmare scenario for the rabid, passionate Red Sox fans. Shortly after the dismissal of previous President of Baseball Operations/General Manager, Dave Dombrowski, reports surface that the Red Sox would seek a cost controlled MLB outfielder that could slot into the 2020 lineup, a mid-rotation starting pitcher, and two Top-100 overall level prospects, if they ultimately made the decision to put Betts on the trade block. That report seemed to line up with the desire to shed salary, and would kick start the franchise’s efforts to revamp the farm system. Now, with Bloom on board, it has been rumored that the organization may look to attach a high-priced contract like David Price to Betts for a lesser return, in a effort to clear even more money. While that type of move would single-handedly allow the team to reach their financial goals, the team would have a lineup without Betts, and a need for (at least) two starting pitchers, with Price gone, and Rick Porcello departing via free agency. Not getting back at least one premium prospect to give the fan base hope that perhaps one day they can see Mookie’s production replaced in the lineup by a player that will be around for awhile seems like a drastic measure to avoid signing their franchise player to record breaking extension and clearing an additional $30M+ per season for the next three years in Price’s deal, but Henry’s track record in dealing with such matters may justify the arrogance that comes with such a move. Of course, there is another side to this story…

The Player: A Franchise Cornerstone

Mookie Betts rise to one of Major League Baseball’s elite players has been a fascinating journey. Drafted in the 5th round in 2011, the undersized second baseman was one of the league’s best hitters at each stop in the minor leagues. With his path to playing time blocked in Boston by former MVP, Dustin Pedrioa, Betts made the transition to the outfield to find playing time at the big league level. The results: a perennial all-star and MVP candidate, multiple Gold Gloves and Silver Slugger awards, and a 2018 World Series ring. He’s positioned himself to sign what could possibly be the richest contract in MLB history when he becomes a free agent after the 2020 season. A homegrown, drafted and develop superstar, Betts has a chance to cement his legacy alongside Larry Bird, Tom Brady, and Ted Williams as a true Boston sports icon. But will he?

As he enters his final year under team control, his message to the fans, the media, and the organization hasn’t wavered. He loves the city, loves the fans, Boston is all he’s ever known…but it’s a business, and he’s content to play out the the remainder of his current deal and test free agency when the time comes. That message seems simple and free of controversy, but it’s also a reminder that the player has all of the leverage in this situation. The one thing that he hasn’t said is that “Plan A” is to stay in Boston. While it’s quite clear that Betts is aware of the business side of his upcoming contract negotiation, and after watching this ownership group spend recklessly in the free agent market during his tenure with the organization, expecting him to take a “hometown discount” to stay in Boston would be naive, especially after watching inferior players cash in $300M+ contracts in recent off seasons. A simple message to ownership along the lines of “pay me accordingly and I’ll spend the rest of my career here” would at least give the organization an inside track on what it would take to keep him for the foreseeable future. Without an assurance that a deal can be made before Betts hits the open market, the front office finds themselves in a position where they could realistically lose Betts after the season and only recoup a compensatory draft pick in return. That uncertainty fuels the incessant trade rumors.

Mookie Betts is the single best homegrown, drafted and developed player that the Red Sox franchise has had under the current ownership regime, spanning nearly two decades. In that time John Henry and Co. have given out outlandish free agent contracts to likes of J.D. Drew, Julio Lugo, Carl Crawford, Pablo Sandoval, Hanley Ramirez, David Price, Nate Eovaldi, and a recent extension to Chris Sale. In just about all of those cases, the contracts were complete disasters, with only the Sale deal providing any hope of return on investment. Betts himself has been a part of the organization as most of these egregious deals have been signed. He’s witnessed first hand as the front office has tried to vault the team into title contenders by irresponsibly throwing money at their problems. To ask, or expect him to take less, or to be the one to help them atone for reckless spending in the past is glaringly unfair. He’s worked hard, and he’s earned the right to be rewarded with one of the largest contracts in the history of the game. The lines of communication need to open between the organization and the player, with the end result keeping him in a Red Sox uniform for many years to follow.

The Fans: Waiting for an Answer…

Mookie Betts really is the perfect player. Free of off the field controversy, no whispers of PED use or failed tests, dazzling on the field performance that presents a real opportunity to see something special on any given night, and a pillar in the community. With his recent “it’s a business” stance, message boards, comment sections, and water cooler talk are using terms like “disloyal” or “greedy” to describe this generational player who’s done everything right since the day he was drafted in 2011. The franchise, just a year removed from the greatest season in franchise history, is in flux. The farm system lacks elite talent. The payroll is bloated, and on-field performance isn’t matching the checks that are being written. Directing the frustration that comes from a disappointing season and an uncertain future toward Mookie Betts is misguided. While the mantra of most die-hard fan is “root for the laundry, not the player”, seeing Mookie put on another uniform will be different. Do you really think that superstar player that takes time out of a World Series run to feed and care for the homeless in Boston in the wee hours of the morning, under the cloak of anonymity, doesn’t want to be here? 

The Result: To Be Decided…

Sustained success and World Series championships can mask organizational dysfunction. Chaim Bloom will be the fourth president of baseball operations in Mookie Betts tenure with the organization. He was drafted by Theo Epstein, developed under the watchful eye of Ben Cherington, and crowned MVP and World Series Champion with Dave Dombrowski at the helm. Bloom is now in charge of next phase of Mookie Betts impressive career. Can he really be the guy that lets Mookie get away? Let’s hope that he does everything he can to keep him here. That he fully considers the team, the player, and the fans when making what might be the biggest “business” decision of his career.