Red Sox have no one but themselves to blame for Mookie Betts mess

CLEVELAND, OH - SEPTEMBER 23: Mookie Betts #50 of the Boston Red Sox reacts after striking out during the ninth inning against the Cleveland Indians at Progressive Field on September 23, 2018 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images)
CLEVELAND, OH - SEPTEMBER 23: Mookie Betts #50 of the Boston Red Sox reacts after striking out during the ninth inning against the Cleveland Indians at Progressive Field on September 23, 2018 in Cleveland, Ohio. (Photo by Jason Miller/Getty Images) /

The Red Sox are most likely going to part ways with the best player they’ve developed in decades and they’ll have no one to blame but themselves.

As speculation continues to run rampant on the ultimate fate of Mookie Betts for the 2020 season, it’s worth once again looking at how and why the Red Sox are in the situation they’re in with their best player. It’s not often that teams try to actively shop one of the best homegrown players they’ve produced in the last thirty years, and even less common that the sole reason centers around the team in question trying to shed payroll and save money.

As we all know (and if you somehow don’t, here’s a refresher), the Red Sox have Mookie under contract for the 2020 season for $27 million. Once this season is over, he’ll be a free agent and has shown no inclination to sign an extension before hitting the open market. The Red Sox are also currently over the $208 million luxury tax threshold, a number they all of a sudden became desperate to get under about halfway through the dismal 2019 season.

While it does make quite a lot of sense to trade Betts before he becomes a free agent in order to maximize their return rather than risking him walking away after the season for nothing, it also seems crazy that the Red Sox wouldn’t do whatever it took to keep him in Boston for his entire career. They have made some offers to him over the last few seasons, but Mookie has turned them all down. A report last week included supposedly new information that Betts countered with a massive request for a twelve-year, $420 million deal.

There has been much wailing and gnashing of teeth across Red Sox Nation at the situation the team finds itself in now. How did they get to the point where they are trying to sell to the fanbase that trading a generational talent like Betts is not only necessary, but the right thing to do? It seems preposterous that the Boston Red Sox, of all teams, find themselves in a situation where they can’t (or won’t) open the checkbook and pay whatever it takes to keep Mookie in Boston for the entirety of his career, and yet here we are.

So how did we get here? I’ve written at length about why the Red Sox suddenly feel the need to shed payroll, as have many others, but the short answer is because they made a series of bad investments (in terms of player contracts) that have all come home to roost at the worst possible time. I refuse to believe, though, that a team as smart and forward thinking as Boston didn’t see this coming down the road and was taken completely by surprise at the timing. If that truly is the case, nobody should have any confidence in them going forward.

To set the stage again, the Red Sox payroll as of the time of writing stands above $233 million, some $25 million and change over the $208 million tax threshold. The simple math shows that unloading Mookie’s $27 million for this season would get them under that threshold and reset the tax penalties, but why are the Red Sox in this predicament in the first place?

This is why:

Chris Sale: $145 million for five years (starting in 2020)

Nathan Eovaldi: $68 million for four years (started in 2019)

David Price: $217 million for seven years (started in 2016)

For just the 2020 season alone, these three will take up a combined $79 million of the Red Sox payroll! Given their injury issues and down productivity over the last couple of seasons (as outlined in a previous article), that is a ton of money tied up in risky contracts. The merits of all three contracts can be and have been debated ad nauseam by myself and others, but the fact of the matter is that the Red Sox showed an alarming lack of foresight and restraint in doling these deals out when they knew they’d have to do something about Mookie after 2020.

As I said last week on Twitter, the Red Sox have a history of overpaying for other team’s best players while low-balling their own homegrown players who have already shown they can handle playing in the baseball crucible of Boston. Look at what they did to Jon Lester, low-balling him to the point where they had to do the same thing they’re trying to do with Mookie, trading him during his final season under contract in order to have something to show for losing him.

However, while the lion’s share of the blame can be laid at the feet of former President of Baseball Operations Dave Dombrowski, Betts also bears a fair amount of responsibility. I hesitate to use the word “blame” since Mookie isn’t doing anything wrong; he’s just exercising his given right to bet on himself in free agency. All of us, no matter what profession, want to be paid the highest dollar amount we can get for the work that we do and Mookie Betts is no exception, nor should he be held to a different standard simply because he’s a baseball player.

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Still, contrast Betts with what his teammate Xander Bogaerts did last year. Bogaerts was due to be a free agent after the 2019 season and is also a client of Scott Boras, who is notorious for his clients not signing extensions with their teams before hitting free agency. Xander ended up surprising everyone by signing a six-year extension for $120 million that will keep him in Boston through the 2026 season. Among the reasons he cited were his comfort and enjoyment playing in Boston and for the Red Sox.

Now, does this make Xander right and Mookie wrong? Not at all. But it does highlight the fact that they knew Mookie has had this approach to his impending free agency for the last few seasons and yet they still handed out massive contracts like drunken sailors to fragile pitchers. Because of this, the Red Sox are feeling the heat because they’ve painted themselves into a corner and have to draw a hard line on what they are willing and/or able to offer Betts.

Was Mookie’s counter-offer to the Red Sox huge? Yes. Does he deserve a contract of that size and length? Probably (we can debate the pros and cons at a later date). Should the Red Sox still be in a position to accommodate Betts and give him what he wants (or close to it) without being over $100 million off from what he’s asking? Yes. Unfortunately, a lack of foresight, sound team building, and fiscal restraint has put the Red Sox in a position where the best move (trading Betts) means parting with a generational talent that has the potential to set the team back a decade.

Next. Betts trade is going to happen. dark

This is supposed to happen to other lesser, poorly run, smaller market teams, not the Boston Red Sox.