How the Boston Red Sox ended up needing to shed payroll

BOSTON, MASSACHUSETTS - SEPTEMBER 29: A general view of the Fenway Park sign and grandstand during the second inning of the game between the Boston Red Sox and the Baltimore Orioles at Fenway Park on September 29, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images)
BOSTON, MASSACHUSETTS - SEPTEMBER 29: A general view of the Fenway Park sign and grandstand during the second inning of the game between the Boston Red Sox and the Baltimore Orioles at Fenway Park on September 29, 2019 in Boston, Massachusetts. (Photo by Maddie Meyer/Getty Images) /

Reviewing the payroll obligations that the Boston Red Sox committed to in recent years that put them in a position where they must now trim the budget.

The Boston Red Sox are one of the marquee franchises in Major League Baseball, a founding member of the American League and an iconic brand. Beloved by Red Sox fans both within New England and without, the team practically prints money.

Coming off of their fourth World Series title in fifteen years in such dominating fashion, most fans (myself included) figured the Red Sox had as good a chance as ever in 2019 to repeat as champions or to at least make a deep playoff run. Instead, they turned in one of the most disappointing seasons in their long history and along the way seemed to adopt a new philosophy of wanting to slash spending and get under the luxury tax thresholds they’ve been well over the last few years. For a team that has spent as freely and almost wantonly at times as the Sox have, this begs the question: how did we get here?

In 2019, the Red Sox carried a payroll of approximately $229 million, well over the $206 million tax threshold. They’ve been operating in this regime for the past several years and seemed content to pay the tax penalties to field competitive teams.

Indeed, after winning the World Series in 2013, they continued to spend money and be aggressive in free agency even when fielding two straight last-place squads in 2014 and 2015. With the maturation of homegrown stars like Mookie Betts, Xander Bogaerts, Rafael Devers, Andrew Benintendi, and Jackie Bradley and free-agent pitcher David Price in 2016 (7 years, $217million), Boston bounced back to win the AL East three straight seasons, culminating with their historic championship season in 2018.

They brought nearly the entire 2018 team back intact in 2019, minus Craig Kimbrel, Joe Kelly, Ian Kinsler, and a few other less significant pieces. It looked like they were primed to mount a credible defense of their title until the season actually started.

After waiting for the hot run of games that would vault the Red Sox back into contention that never came, the team was very passive during the run-up to the July 31 trade deadline. While the media and fans were clamoring for the team to address their biggest needs and trade for a reliever or starter, the team instead plucked Andrew Cashner off of the scrap heap and relied on a variety of minor league prospects and career AAAA guys to plug the remaining holes. The end result, as we all know and as I documented in my latest book, Consistently Inconsistent, was ugly.

Along the way, some strange things started happening. Owner John Henry publicly stated that the team was going to have to succeed with what they had because he wasn’t looking to add any more payroll (I’m paraphrasing).  Soon to be deposed head of baseball operations Dave Dombrowski went on the record saying that he wasn’t necessarily given a mandate from above not to add any more payroll, but he was also instructed not to spend much.

As the season limped along to its conclusion, there were multiple rumblings out of the front office (including from team president Sam Kennedy) that the goal heading into 2020 would be to slash payroll and try to get under the luxury tax thresholds. How did the Red Sox, who have spent money like a drunken sailor on leave over the last two decades, go from spendthrift to just plain thrifty over the course of a season? And why?

First of all, the Red Sox are carrying a lot of dead money paying for players who aren’t playing for them. Chief among these is Pablo Sandoval, one of the most disastrous free-agent signings in team history. His money comes off the books shortly, but the $19 million hit in 2019 didn’t help, nor did the $5 million (Eduardo Nunez) and $1.75 million (Tyler Thornburg) hits for two other players who didn’t help out in the slightest in 2019.

There was a lot of injury money tied up, again in players who didn’t contribute ($15 million for Dustin Pedroia, $6.25 million for Steve Pearce). There’s the extension the team gave Chris Sale (5 years, $145 million) which looks worse by the day as he’s been injured since the summer and is only now being cleared to throw again.

Rick Porcello‘s $21 million will come off the books as he’s now a free agent (and unlikely to return to Boston, although you should never say never), but with Mookie Betts making $20 million last year in arbitration and in line to push $25 million+ in arbitration in 2020, the relief there won’t be as large as initially expected.

JD Martinez choosing not to opt-out of his contract in 2020 (to the tune of $23.75 million) also complicates matters slightly. Perhaps the biggest blunder and one which will hamper the team mightily in their quest to shed money is the 4-year, $68 million deal they gave Nathan Eovaldi heading into the 2019 season. Eovaldi’s postseason heroics in October 2018 were the stuff of legend, but the team made the classic mistake of rewarding someone for a run of postseason success when nothing in the entirety of his previous career (a mediocre injury-prone pitcher) suggested he was worth that.

More from Red Sox News

At this point, Eovaldi’s value is at an all-time low, so the Red Sox will have no recourse in trading him. The best they can do for the foreseeable future is to try and get the most out of him by figuring out whether he helps them best out of the rotation or the bullpen.

A series of poor moves and profligate spending (of which I’ve only scratched the surface in this article) over the last decade has come home to roost which all leads to the elephant in the room: Mookie Betts. He’s stated repeatedly throughout his career that he has every intention of getting to free agency, which is his right. The Red Sox have control over him for the 2020 season before he gets there and all indications are that they will not be able to sign him to a long-term deal before that happens.

If Boston hopes to keep Mookie in a Red Sox uniform for years to come, they’re going to have to pony up something in the neighborhood of $30 million per year for, say 7-10 years. Given their sudden about-face in the summer of 2019 from throwing money around to pinching pennies, how likely does look to happen now? And with their public proclamations of intending to do so, what kind of message does that send to Mookie about how serious the Red Sox are in even trying? It’s a terrible corner for the team to have painted themselves into, especially regarding their best homegrown player since Carl Yastrzemski, the seeds of which can be traced back earlier in the decade.

If the Red Sox are serious about wanting to shed payroll and change their organizational philosophy when it comes to team-building and spending, we can expect to have some lean “bridge years” for the next few seasons. This will be exacerbated by how strong the American League is at present… get ready for a lot of third and fourth-place finishes in the coming years.

Next. 5 biggest questions during Winter Meetings. dark

If the team truly lets go of players who are making a lot of money (rumors of various validity are flying around as the Winter Meetings start this week that Mookie, Andrew Benintendi, David Price, and Jackie Bradley among others are available for the right price), the most cost-effective way to replace them will be from the minor leagues. With a relatively barren farm system that desperately needs to be restocked as well as a pitching development department that hasn’t produced anything of worth for almost twenty years (that’s a topic for an article of its own), things are going to be very interesting for the Boston Red Sox as the 2020 season unfolds… and beyond.