Boston Red Sox: Fixing the team in four easy steps

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BOSTON, MA – AUGUST 11: A general view of Fenway Park in the fourth inning of the game between the Boston Red Sox and Los Angeles Angels at Fenway Park on August 11, 2019 in Boston, Massachusetts. (Photo by Kathryn Riley/Getty Images) /

The Red Sox current situation is a mess. How would I try to fix it if I were in charge of the team? Here are four steps that might work.

Let’s play a little game of “what would I do if I ran the Boston Red Sox?” While all of the news and speculation swirling around the team lately has had to do with the status of Mookie Betts, this article is going to look at Mookie’s situation but only as a piece of the entire Red Sox puzzle.

For all of the hand-wringing over Betts, the Red Sox have several other problems to contend with heading into the 2020 season and beyond. The starting rotation has a major question mark looming over it as far as health is concerned. There isn’t a dedicated closer in the bullpen let alone a trusted structure of relievers. Oh, the team still doesn’t have a manager.

Mookie may be commanding the headlines but he’s merely the start of the headaches occurring at Fenway Park. With everything laid out on the line, I’m going to take a seat in the big chair and lay out my plans to fix this mess.

Let’s make a list and tackle them one by one.

BALTIMORE, MARYLAND – JULY 19: Mookie Betts #50 of the Boston Red Sox bats against the Baltimore Orioles in the first inning at Oriole Park at Camden Yards on July 19, 2019 in Baltimore, Maryland. (Photo by Rob Carr/Getty Images) /

Step 1: Mookie Betts

I think we’re all probably sick of the constant Mookie rumors by now. There have been innumerable stories on whether the Red Sox will trade him, where they’ll send him when they’ll do it, and what they can hope to get in return.

I myself have written several articles about the entire situation around Betts and it’s not my intention to dwell on those anymore in this one. This is supposed to be what I would do if I ran the Sox, remember?

So what would I do? First, I would do everything I could to pay Mookie. I’d do everything I could to not pay him the $420 million over twelve years that he supposedly asked for, but I’d try to improve upon the $300 million and ten years the Red Sox did offer.

Meeting in the middle, an offer of around $380 million for ten years should get it done. That would put him at an AAV of $38 million, but I would structure the contract a bit differently.

I’m frontloading this contract so that the majority of the money is paid out in the first five or six years. Mookie is twenty-seven right now which means he’ll be twenty-eight when this contract would kick in.

With most players entering their decline phase in their early-to-mid thirties, I’m not going to want to pay him $38 million a year in his age thirty-four to thirty-eight years…just look at Albert Pujols (or soon, Giancarlo Stanton) as a cautionary tale.

Ideally, I would structure his deal such that ~65% of the money ($247 million) would be paid over the first five years of the deal (at a whopping $49.4 million/year…remember, this is just hypothetical).

The remaining $133 million would then be paid out over the final five years (at $26.6 million per year). While those numbers are staggering, it would at least guarantee that the Red Sox are paying the largest amount of money for Mookie’s most productive years.

Frontloading Mookie’s contract also gives the Red Sox flexibility down the road. Since they won’t be paying as much in his decline years of age 34-38, the $26.6 million/year won’t hurt as bad (and by the time he gets there in 2026, that’ll probably look like a steal).

Also, if they decided to trade him to a team that might want a veteran player, it would be a lot easier to offer someone making $26 million than $38 million.

I know these numbers seem crazy and this scenario seems unlikely and I also know that it would be contingent on Mookie meeting the Red Sox in the middle (let’s assume for the sake of this article that he does), but if it were up to me I’d give it some serious thought.

BOSTON, MASSACHUSETTS – JANUARY 15: Red Sox Chief Baseball Officer Chaim Bloom talks with the media following a press conference addressing the departure of Alex Cora as manager of the Boston Red Sox at Fenway Park on January 15, 2020 in Boston, Massachusetts. A MLB investigation concluded that Cora was involved in the Houston Astros sign stealing operation in 2017 while he was the bench coach. (Photo by Maddie Meyer/Getty Images) /

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.

DENVER, CO – AUGUST 28: Starting pitcher Eduardo Rodriguez #57 of the Boston Red Sox delivers to home plate during the first inning against the Colorado Rockies at Coors Field on August 28, 2019 in Denver, Colorado. (Photo by Justin Edmonds/Getty Images) /

Step 3: Pitching

As I’ve written about before, all of the Red Sox problems in 2019 stemmed from pitching. The bullpen has been neglected for several years and is a patchwork of guys who aren’t that talented with no defined roles (who the hell is the closer?). However, in 2019 they actually pitched pretty well under the difficult circumstances they were placed in. What really let the entire team down was the starting rotation.

Right now the Red Sox look to start the season with a rotation of Sale, Price, Eovaldi, Eduardo Rodriguez, and Martin Perez. The team has a dismal track record of developing pitchers over the last two decades so there isn’t much relief coming from the minor leagues. Still, going hand in hand with my proposals to trim payroll, the first thing I do is whatever it takes to unload Price, Sale, and Eovaldi.

Those three are all injury prone and at the age where many starting pitchers start their slow and inevitable decline. I love Sale as a competitor and when he is on, he is one of the best pitchers in the game and a pleasure to watch.

Still, he’s broken down in the second half of each of the last three seasons and with his slender frame, unorthodox delivery, and being on the wrong side of thirty his career looks to get worse, not better. Price has overall been durable throughout his career but he’s battled nagging injuries over the last two seasons which have affected his performance and will only get worse as he nears thirty-five.

Eovaldi is the youngest of the bunch at thirty but has also been the most injury-prone. He’s already undergone two Tommy John surgeries as well as his procedure to clear out loose bodies from his elbow in 2019. If it were up to me, I’d do what I could to unload those three which frees up a ton of money and also leaves me with a rotation of…Eduardo Rodriguez and Martin Perez. So now what?

Assuming his 2019 season wasn’t an aberration but is the new norm going forward, I have Rodriguez anchor my staff and try to patch the rest together with Perez, Brian Johnson, Hector Velazquez, any cheap arms I can get on the open market, and anyone who I can bring up from the minors who I think can cut it (Darwinzon Hernandez?).

Whether that means bringing not-ready-for-primetime guys like Bryan Mata, Jay Groome, Tanner Houck, Durbin Feltman, and Noah Song up and letting them take their lumps at the big league level as starters and/or relievers, I don’t know. Similar to the payroll issue, the Red Sox pitching woes are legion and won’t be easy to solve.

I don’t like this part anymore…let’s keep moving along.

OMAHA, NE – JUNE 28: Third basemen Bobby Dalbec #3 of the Arizona Wildcats hits an RBI single against the Coastal Carolina Chanticleers in the first inning during game two of the College World Series Championship Series on June 28, 2016 at TD Ameritrade Park in Omaha, Nebraska. (Photo by Peter Aiken/Getty Images) /

Step 4: Rebuilding the Farm System

Rebuilding the depleted farm system is an absolute must. At the start of the 2019 season, the Red Sox farm system was ranked 30th out of 30 teams and by the end of the season (after the draft), it was ranked…30th out of 30 teams.

During his time with the Red Sox, Dave Dombrowski did what he’s always done throughout his career and traded the team’s top prospects for major league talent in order to win immediately. This approach has worked for him as he won a World Series with the Miami Marlins, two American League pennants with the Detroit Tigers, and a World Series with the Red Sox.

However, what he’s left in his wake at all three stops is a decimated farm system and a barren talent pipeline to the major leagues. The Red Sox situation is fairly dismal, with their top prospects barely cracking the top seventy of MLB’s top one hundred prospects. With the team being over the luxury tax threshold over the last several years and thus losing draft slots every year, they haven’t been picking as high as they should be.

If we still pretend that my hypothetical Mookie deal from above has happened, this looks to be the case for another two or three seasons until some big money comes off the payroll.

What do we do to fix this? The best course of action (after dumping the three pitchers I hypothetically dumped above which instantly got us under the tax which reset the penalties) would be to do much the same as what Bloom has been doing since he came aboard.

Small low-risk/low-reward deals for prospects to replenish the minor leagues and hopefully hit on a few prospects is crucial just to stock the farm with some talent. If they can offload some of their current lower-level major league talents in trades to bring back multiple prospects in return, that would kill two birds with one stone in shedding money while stocking the minors.

Of course, the Red Sox need to continue to scout and draft smartly while developing talent at all levels as these players are either the future in Boston or somewhere else (and can bring back major league talent in return).

This is not an easy fix nor is it a quick one…rebuilding the minor league talent pool will take several years, but it goes hand in hand with dumping payroll and resetting the tax penalties, so as long as these approaches are working in synergy, things should (hopefully) turn out fine.

TORONTO, ON – JULY 04: Michael Chavis #23 of the Boston Red Sox hits a 3 run home run in the sixth inning during a MLB game against the Toronto Blue Jays at Rogers Centre on July 04, 2019 in Toronto, Canada. (Photo by Vaughn Ridley/Getty Images) /

Finally, how would I hypothetically wrap it up and construct the big league roster going forward? I’m planning on rebuilding around Mookie, Xander Bogaerts, Rafael Devers, Michael Chavis, Rodriguez, and (assuming I can still afford them) Andrew Benintendi and Jackie Bradley.