Mookie Betts and Xander Bogaerts

Dave Dombrowski and the Three-Year Window

Yesterday, Rob Bradford of WEEI spoke to Mookie Betts and Xander Bogaerts at the Boston Baseball Writers’ Dinner. He asked them if they were interested in signing contract extensions to stay in Boston. There was slightly more nuance to their answers but in essence both said “no.” That puts a fine point on where the Red Sox are right now as an organization. Bogaerts has three more seasons (including 2017) in Boston before reaching free agency. Betts has one more than that. Additionally, David Price has two seasons before he can opt out. Hanley Ramirez has two seasons before his contract expires. Rick Porcello has three. Chris Sale has three more seasons on his deal as well. You may be sensing a theme here. This group will be here for about three seasons. After that? Who knows, but it’ll likely involve massive turnover. 

Of course most teams don’t have their core locked up to eight-year deals. While it would be wonderful if the Red Sox signed Jackie Bradley, Betts, Bogaerts, and heck, Andrew Benintendi to multi-year contract extensions, that’s probably not particularly realistic. But once this tide recedes, we’re still going to need a place to sail our boats.

The issue is the timing. In three seasons’ time the majority of the important players on this Red Sox team will hit free agency. Ideally a franchise would have minor league players ready to take over as players on the major league roster depart, but Dave Dombrowski’s aggressive use of prospects to acquire major league players over the past season and a half has cut the depth out of the Red Sox system. It could be replenished to some extent over the next three seasons, but the draft and the rules of the international amateur market don’t work to the Red Sox’s advantage like they once did. Boston will be able to add young talent, but draft position, pool money, and international signing limits will combine to make it very unlikely they’ll be able to put themselves into a similar position to the one they were in at the start of Dave Dombrowski’s tenure. 

So in three years when the above players’ contracts end, who will pick up the torch? Over the last year and a half, Dombrowski has traded away Logan Allen, Javier Guerra, Carlos Asuaje, Manuel Margot, both Basabe brothers, Maricio Dubon, Josh Pennington, Pat Light, and Anderson Espinoza. That’s a ridiculous amount of talent to give up, and that’s not even the complete list because I didn’t mention the four guys he traded away in the Chris Sale trade. 

The Chris Sale trade. Oh man, the Chris Sale trade. That deal made some things clear. 

Dave Dombrowski is clearly a different guy than Ben Cherington. His first off-season told us that much. There is no way if you tied Ben Cherington naked to the front of a city bus and put giant crabs on his nipples that he makes the Craig Kimbrel trade. Maybe he might sign David Price. Probably not, but we can squint hard enough that our noses bleed and convince ourselves it could be possible. But the Kimbrel deal would never, ever happen under Cherington’s watch, I don’t care how sharp the crabs’ pinchers are. 

So if the Kimbrel deal was a planet too far for Cherington, the Sale trade is in another galaxy entirely. Let’s look at the Sale trade for a second and all the things it tells us about Dombrowski’s Red Sox. Sale is a big star, he’s a big name, he’s under contract for three more years, and he cost the Red Sox their best prospects, but notably nobody off their major league roster. That’s a lot to take in, but I think it says something important about where the Red Sox are right now. It says they’re trying to win right now and for the next few seasons, and any time after that may as well be in another century. Or in a beach house on the edge of an eroding cliff. 

Ideally a baseball organization rolls along like a bus. It stops every now and again for some people to get off, but usually others get on as well. The job of the GM is to keep all the seats filled with quality players. The perfect case scenario would see an almost seamless addition of players from the minor league system to the major league roster, with the occasional free agent signing as needed. The Red Sox were pretty close to that ideal, about as close as could reasonably be asked, when Dombrowski took over. But even if we don’t go back that far, the entire 2017 outfield, shortstop, and catcher all feature young cost-controlled above average talent. With David Price and Rick Porcello standing at the front of the rotation and Kimbrel already in place in the pen, there wasn’t much need for big additions. The team had payroll space, but it also (miraculously) still had a very good farm system with talent percolating up toward the majors. The bus was full, and even though a few guys were getting off, there were more than that many waiting to get on. This was the best of both worlds. 

The Sale deal didn’t blow that all to high hell by itself, but it’s close. The major league team is undoubtedly better now with Sale on the roster, but down the road they’re short four prospects, two of which were as likely as any to be able to step in and help the major league roster. It’s a delicate balance that was built by Cherington, and Dombrowski has trashed it by trading away (at least) 15 minor leaguers who could have combined to give the Red Sox up to 105 player seasons.

This is roster building by sledgehammer and it’s not my style. But that doesn’t mean it can’t work. The problem with any free agent contract is that by spending money in one place it prevents you from spending it elsewhere. However, if payroll is no concern, if you could sign Pablo Sandoval to a five-year contract in one off-season and then Manny Machado two off-seasons later, then the only real issue becomes filling each roster spot with the most talent you can pack into it. That’s sort of what Dave Dombrowski has tried to do. He’s probably not a dollars-per-WAR kinda guy, but if you look at it that way just for a second, Dombrowski has tried to pack the most WAR into each roster spot he can. 

He’s not counting pennies either. There’s no sense waiting for minor leaguers to show up and then waiting longer to see if they can hack it in the big leagues when you can fix the problem far quicker than that. If giving up Logan Allen will get Craig Kimbrel in a Boston jersey, fine. The problem is that there is a limit. No team, even the Red Sox, can spend infinitely. That goes for trading minor leaguers for major league talent as well, because eventually the farm system dries up. 

There is something to be said for having everyone on the roster peak at the same time. It’s how the 2001 Mariners won 116 games. Even better example: it’s how the 2013 Red Sox won the World Series. The next three seasons could be that level of special for Boston. If they are we’ll hold them close, like we do with the 2013 champs. But even if, what happens after that? Cherington had a plan. So did Epstein before him. There’s still time for a plan, but right now it certainly appears as if in three seasons the core of the team is going leave and there won’t be anyone waiting to get on the bus.

Photo by USA Today Sports Images

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7 comments on “Dave Dombrowski and the Three-Year Window”

Walt in Maryland

Any contract Bogaerts or Betts signed right now — both are 24 — would almost certainly wind up costing them tens of millions of dollars down the road. Easy to see why the Red Sox would want to do it, but it makes no sense for them.

cranky yankee

Your article only tells half the story. Cherington got lucky with the Dodgers taking away a boatload of mistakes left to him by Epstein . When he was in it to go for it now. The Red Sox are not even spending recklessly being under the cap. Prospects are suspects until proven otherwise. call me in 7 years tell me how the Padres and white Sox are doing


This doom n’ gloom analysis would be true – if the Red Sox were a small market team completely reliant on homegrown talent and had no money to hire said talent when it approached free agency.
The Red Sox, however, are not that team. I assume one reason a push is being made to get under the cap this year is to make it easier to pay for that talent down the line.


Walt, “almost certainly” as long as they stay healthy and maintain or improve current performance levels. I don’t understand why a younger player would insist on rolling the dice when they can guarantee themselves more wealth than most people can even dream about. I can’t agree that it “makes no sense for them.”

Walt in Maryland

Well, yes, some players clearly prefer the certainty to the risk of injury or regression.

But Bogaerts (Bradley too, I believe) is represented by Scott Boras, and his track record is pretty clear. His players get paid what the market will bear, usually by going to free agency.


Just because Betts and Bogearts don’t say they want to sign doesn’t mean they won’t sign. What do you expect them to say? “Please, Please, Please”? Or even better for PR: “Well, really they need to pay me a tremendous amount and then I’ll sign.”

The Red Sox long-term questions under Dombrowski are real, but Mookie and Xander’s answers to a couple of media questions have nothing to do with that.


I don’t really get this argument. It may make some sense if the redsox had no future financial flexibility or if their core players like Sale, Betts, Bogaerts, ect were in their 30s, but their not.

The article mentions all the good players who could leave, but fails to mention all the overpaid players like Hanley, Sandoval, Craig, and Castillo who will be off the books. That right there clears almost 70million AAV. You know what you can buy with that money? Extensions for Betts and Bogaerts, and then some

You mention Price, Porcello, Kimbrel all hitting FA, but forget the contracts that would go with them. the three combine to make almost 70million as well). You could probably extend all three for similar money or use that money in other places.

Also, don’t forget the young cornerstone players like Trout (yes Trout), Kershaw, Harper, Machado, ect that are all eligible for FA in that 4 yr period as well.

Reality is, while the redsox have a ton of players who could hit FA in next 4trs, they also have a ton of money, enough money to extend most of their players.

Also, let’s not act like Devers, Groome, Benintnedi, Erod, Swihart, Travis don’t exist. 2 of those guys being 3+ WAR players along with extending the young core (which the team has money to do) and suddenly the redsox are looking quite good in later seasons.

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