It's Looking Like The End Of An Era

On the impending and extreme roster turnover in Boston

Photo by Lauren Thimmesch on Unsplash

Since the season started it’s easy to focus on the games. At first, winning is exhilarating and losing is maddening, but as the season goes on, you settle in to the ups and downs of it all. I have to relearn ‘there’s always tomorrow’ every year. What might be lost in the focus on the field, is how this Red Sox team is set for an avalanche of turnover this coming off-season. With each leaked detail the idea that the team could remain together looks less and less likely. If you’re a Red Sox fan and you just want the team to win regardless of whoever is wearing the uniform, that’s fine. But if you’ve grown accustomed to seeing certain faces and names, it’s looking like a bumpy ride is in store.

Let’s get into it after I say hi.

Hi! I’m Matt Kory and this is Sox Outsider. Welcome! You might know my writing from The Athletic, FanGraphs, Over The Monster, or a bunch of other spots. I’m here now and covering the Red Sox. You’re here too, so why not stick around? It’s pretty easy. Just click the button to subscribe. It’s free, so why not? Thanks.

During the off-season I’m an MLB Trade Rumors guy. I read the Boston Globe and The Athletic and a bunch of other sites, but the easiest place to check up on all the baseball moves and rumors is MLBTR. I go there multiple times a day to keep up. But once the season starts, I’m watching games and reading about those games and the players who play them, and I don’t tend to go over there nearly as often. Sadly these last few days I’ve been at MLBTR a bit too often, as reports of the Red Sox negotiations with their free agents-to-be have leaked out.

This version of the Red Sox has looked pretty static for a few years now, and some of the main characters have been around for even longer than that. This isn’t the 2018 team, but you wouldn’t be wrong to call it the remnants of, or a descendant of the 2018 team. Heck, Xander Bogaerts is a remnant of the 2013 team. But 2018 was his first World Series win as a starting player. Same with JD Martinez, Jackie Bradley Jr, Mookie Betts, Rafael Devers, Christian Vazquez, Matt Barnes, Nathan Eovaldi, Chris Sale, and Eduardo Rodriguez. They’re not all here anymore, but most of them are.

There’s ebb and flow to all baseball teams. It’s just the nature of the game, as players age in and out of the sport. Anyone can build a winner, it’s staying a winner that is the real and true challenge. It’s why the Red Sox most impressive World Series winning team is, to me, the 2007 squad. But I digress. The Red Sox have a roster with a number of players who are poised to either get paid or move on to other teams, and if that happens someone else is going to have to step into their shoes.

This situation is highlighted by some recent reports on the team’s attempts to extend their core players. Xander Bogaerts has an opt-out after this season which he will certainly use. Rafael Devers will be a free agent following next season. JD Martinez, Christian Vazquez, Jackie Bradley, Jr., Nathan Eovaldi, and Enrique Hernandez will all be free agents following this season. That’s a significant portion of the roster, and over half of the starting lineup set to hit the market.

If you like this group, the news on them sticking around isn’t good. Reports say Rafael Devers and the Red Sox didn’t come anywhere close on a contract extension, and the Red Sox offer to Bogaerts was borderline insulting, and the borderline part is probably unnecessary. And then yesterday, reports surfaced that the Red Sox won’t be extending Nathan Eovaldi either, as their ace starter isn’t willing to discuss a contract during the season. In other words, the Red Sox had their shot and didn’t take it, or worse, took it and missed badly.

The Red Sox have the money to meet the demands of most of if not all of these guys. The issue with that is in five years or so the team will be old and super expensive. You might not want to be pay Xander $30+ million into his later 30s, $25+ million for Eovaldi into his mid-30s, about the same for JD into his late 30s, and so on. It adds up real fast. And worse, it will lead to an inflexible, old, and ultimately bad roster.

But this sucks. There are some guys who it feels like should always be Red Sox, but sadly that’s not the way things go. I remember Jon Lester. That should’ve been an easy contract extension, but the Red Sox didn’t want to pay him market rate into his 30s and so they traded him. Same with Mookie. He was set to go to free agency, but he was also willing to listen to a good market-rate contract offer, but the Red Sox never made one. So many guys who we think of as Ultimate Red Sox players ended up in another uniform. Wade Boggs, Roger Clemens, Kevin Youkilis, Lester, Mookie, Benintendi (maybe I’m the only one who misses Benny)… heck, a whole bunch of that 2004 team left Boston, including Pedro Martinez who signed with the Mets and later played with the Phillies.

It’s more likely than not that your favorite Red Sox, the guy who came up with the team, ends up elsewhere. And that really sucks.

But it’s not necessarily wrong. It’s not my money, so I’m more than happy for them to run a $500 million payroll. Pay Xander $35 million until he decides to retire at age 50. I’m all for it! But we know that’s not realistic. And as much as it sucks, if the front office is working within a budget, which we know they are, some of our favorite players are going to have to go. It makes my hair fall out and my eyes bleed, but it has happened before and it’ll happen again. Watching this take place is, sadly, part of being a fan.

I’m not saying I don’t care. I care! I want Xander and Devers and JD and Nasty Nate to stick around forever. Heck, bring Mookie back and re-sign Kevin Youkilis and Mark Bellhorn while you’re at it. I’m just saying it doesn’t matter whether you like it or not, this is happening. Maybe not across the board, but on some level, and likely a large one, it’s happening.

Maybe they find common ground with Xander. It doesn’t seem likely given the specifics of the reports, but it’s certainly possible. Maybe Eovaldi tests the market and decides Boston is the best spot for him. Maybe Devers decides he wants to stay and the Red Sx decide he’s their guy and they both make a commitment to each other. Maybe they bring JD back on a two year deal with a team option. Maybe maybe maybe… And I wouldn’t bet against any one of those things happening. But all of them won’t.

That will hurt. If you care about the Boston Red Sox, losing the guys you fall in love with, the guys who you go to battle with, the guys we’ve won with, losing your guys is going to sting. I still can’t look at Mookie in a Dodgers uniform, or Lester in a Cubs uniform. Maybe that’s childish, but it still cuts deep. But it happened, regardless of how I feel. The trick is to have a team smart enough to turn that pain into something worthwhile on the field, and last season was a pretty good indicator that the people in charge can do that.

I feel strongly that this is a super smart and extremely capable front office. They’re going to make mistakes because every front office makes mistakes, but they’re going to make more great decisions than mistakes. If you look at Chaim Bloom’s track record since taking over, it’s a pretty strong one.

Last year’s roster didn’t win the World Series, but who among us had them two wins away from the Fall Classic? Hunter Renfroe, Enrique Hernandez, Garrett Whitlock, Nick Pivetta, Christian Arroyo... these are all guys the current front office plucked off the scrap pile or outright stole from other organizations. You’d be hard pressed to come up with a similar list for the last few Red Sox front offices’ entire tenures.

The front office is going to make what they consider to be the best decisions for the long term health and success of the Red Sox roster. That’s good. That’s what they should do. The fact that that health and success might not include Xander Bogaerts and Rafael Devers supremely sucks, but that opens up roster and payroll space to spend on other players.

I’m never going to argue for letting ‘our guys’ go. I guess what I’m saying is it’s good I’m not handing out John Henry’s cash because the Red Sox roster would consist of a 50 year old catcher, a 50 year old pitcher, and Xander Bogaerts extended to the year 3000.

There’s going to be a lot of turnover on this roster in the next calendar year, and if this season doesn’t go to plan, it could happen a lot sooner. It’ll hurt and that pain will dull over time but it may never go away entirely. The only good news to be offered is that I trust the people in charge to make more good decisions than bad and, ultimately, to build a very good team.

So we have that to fall back on, if it helps you feel any better. I’ll be honest and say, for me, it probably should, but I’m not sure it does.

Thanks for reading.