Boston Red Sox: Fixing the team in four easy steps

Step 2: Fixing the Payroll

This one isn’t going to be quite as sexy or exciting as the Mookie deal, but I think we can all agree that while the Red Sox print money, they’ve made some horrendous financial decisions over the last few years, many of which are finally starting to catch up to them.

With a total payroll of $231 million and change, the team is currently ~$23 million over the $208 million luxury tax threshold. Since it’s based on end-of-season payroll, nothing the Red Sox do right now will affect the payroll until 2021.

Keeping that in mind and also keeping in mind that the Red Sox spend more than anyone in Major League Baseball other than the New York Yankees, I’d pay Mookie as I proposed above since it wouldn’t take effect until 2021 and thus wouldn’t affect the 2020 payroll.

I’d take the hit this year and pay the luxury tax penalty and lose the spots in the draft; the Red Sox have operated this way for years, so what’s another year?

With that being said, if I were Chaim Bloom I’d work like hell to unload some of the big, bad contracts the Red Sox have given out over the last several years. If I could find someone to take on David Price, Nathan Eovaldi, and yes, even Chris Sale, I’d do it in a heartbeat.

If I have to eat a portion of the salary to do so, I still do it. Those three make a combined $79 million against the 2020 payroll so even if I have to eat half of those salaries, that still saves me ~$39 million starting next year.

Obviously this is assuming the Red Sox could find a willing trade partner for each of those pitchers. If they can’t, there’s not a ton they can do to shave off money although there are some options. They need to figure out something with Dustin Pedroia, who is due to make $13 million in 2020 and whose playing career is over in all but name.

Whether they can orchestrate a buyout or somehow spread out the remaining $25 million they owe him over an extended period of time to lessen the payroll hit (I’m not clear on if this is allowed or not), they need to get him off the books.

The worst-case scenario would be to ride out the next two to three seasons while taking the luxury tax penalty hits in order to clear off Pedroia’s contract (which ends in 2021), Price’s (ends in 2022), and Eovaldi (ends in 2022).

Along the way, it will also mean not being able to pay Andrew Benintendi (due to make $4.9 million in 2020, a number that will probably rise in arbitration over the next two seasons before he becomes a free agent in 2023) and Jackie Bradley ($11 million in 2020, free agent in 2021). Trading either or both of these guys would clear nearly $16 million off the payroll.

But you know what? The Red Sox situation is such a mess that they’d be wasting the prime years Mookie has left after they just gave him that huge (hypothetical) contract. You know what else? I realized I’m not good at this payroll stuff and I’m glad I’m not the one having to clean it up. What a disaster! Let’s move on.