Why the Red Sox Will Deal Mookie Betts

The Red Sox find themselves in a quandary this offseason. After having the highest payroll in the game for two consecutive years (the latter of which resulted in a third-place finish in 2019), ownership has stated its objective to lower the club’s payroll below the $208 million Competitive Balance Tax (CBT) threshold next season.

As it stands, the team has a projected payroll of $230 million next season (according to Fan Graphs), which means that roughly $22 million will somehow need to be shaved off to meet ownership’s objective.

This has led to the notion that the Sox may seek to trade Jackie Bradley Jr. this offseason. The center fielder is projected by MLB Trade Rumors to get $11 million in arbitration, a sum that surely outstrips his actual value. However, even if the Sox trade Bradley, they would still be about $11 million above the CBT. And then the Sox would need to replace Bradley, which would require an outlay to his successor. Perhaps the Sox can find a replacement for half the cost of Bradley, but that would make it even more difficult to get below the CBT.

Also, keep in mind that the Sox still need to find a fifth starter to replace Rick Porcello, who will most likely depart as a free agent. Though the team will surely experience a savings from Porcello’s $21 million annual salary, the entire $21 million won’t be eliminated since the Sox will still need to pay another starter.

The most obvious solution would be to trade Mookie Betts, who is projected by MLB Trade Rumors to receive $27.7 million in arbitration for the 2020 season.

Though the notion of trading the former MVP is heresy across Red Sox Nation, Betts has repeatedly insisted that he is determined to find his true market value in free agency next year. Though the Red Sox have previously tried to engage Betts’ in contract negotiations, to no avail, management has stated they will try once again this winter. It may be a last stand.

Betts admitted that he rejected an offer from the Red Sox following the 2017 season, which Joel Sherman of the New York Post reported was an eight-year, $200 million proposal. Betts will likely use Bryce Harper’s 13-year, $330 million contract and Mike Trout’s 12-year, $430 million extension as the parameters for his pending deal.

Betts may be better than Harper, but he is undoubtedly inferior to Trout, who isn’t merely the best player of his generation, but one of the greatest players of all time. Even if the Red Sox get Betts to agree to a 10-year contract, for whatever amount, its reasonable to ask if this is the best allocation of precious resources. Though Betts just turned 27 in October and is in the prime of his career, contracts of such length almost never turn out to be wise investments for the teams that agree to them.

Remember, a 10-year deal would pay Betts through his age-37 season. For comparison, Dustin Pedroia is 36 and has appeared in just nine games over the past two seasons; that was unimaginable when he signed his extension.

Consider the Red Sox history with long-term deals, which, for argument’s sake, I will refer to as any deal of at least five years in length. The following contracts are listed in total dollar value:

David Price - seven years, $217 million in 2015

Chris Sale - five years, $145 million in 2019

Carl Crawford - seven years, $142 million in 2010

Dustin Pedroia - eight years, $110 million in 2013

Daisuke Matsuzaka - six years, $52 million, plus $51 million posting fee (total = $103 million) in 2006

Pablo Sandoval - five years, $95 million in 2014

Rusney Castillo - seven years, $72.5 million in 2014

Nathan Eovaldi - four years, $68 million in 2018

Does anyone think that the Red Sox, in retrospect, would sign any of those contracts today? I think the clear answer is no. The team has been burned time after time. The Manny Ramirez deal (eight years, $160 million) was the only long-term pact that delivered true value.

The reality is that almost any contract of more than five years ultimately proves to be a mistake; teams are always paying for past performance.

John Henry and Tom Werner may reason that the Red Sox, with Betts leading the way, still finished in third place last season. Given their budget ambitions, there is no basis to argue that the Red Sox will markedly improve this winter or that the Yankees will regress. The Sox may be battling for second or third place once again, which ownership may rightly argue they can also do without Betts.

If Betts leaves as a free agent next offseason, the Red Sox would only get one compensation draft pick. If they trade him now, however, they might get as many as three proven prospects -- perhaps a team's top-five prospect, another top-10 prospect and a top-20 prospect.

Betts is undoubtedly a dynamic player, who possesses true five-tool ability. He is highly popular in New England, and for good reason. Yet, it’s a virtual certainty that whichever team signs Betts to his next contract will overpay and commit far too many years.

As I've argued previously, long-term contracts are bad for baseball — at least for the teams that sign them.

As it stands, the Red Sox will have five players on their roster making at least $20 million next season, three making at least $25 million and two making at least $30 million.

David Price - $32M
Chris Sale - $30M
Mookie Betts - arb estimate ~$27M
JD Martinez - $23.75M
Xander Bogaerts - $20M

Betts' next contract will almost certainly pay him at least $30 million annually. The big question is, how many $30 million contracts can one team carry -- even a big-market club like Boston?

My thinking is that the Red Sox will have at least one too many, no matter what.