Boston Red Sox

We posed this question yesterday on the Felger & Mazz show – or, more, specifically, my partner did – and I thought it was a great way to frame it:

Given where the Red Sox are and the challenges they face in terms of keeping their team together … do you trust Dave Dombrowski?

And I don’t.

Crazy, right?

Dombrowski has been the Red Sox president of baseball operations for three years no and he has three division titles to go along with a World Series championship. The Red Sox just had the greatest season in their history – let’s not confuse that with the greatest team – and they have the large majority of the roster intact. SO what’s the problem?

The future, that’s what.

Fact: starting this offseason, the following Red Sox players may all be eligible for free agency – Craig Kimbrel, Xander Bogaerts, Chris Sale, Rick Porcello, and J.D. Martinez. A year later, Mookie Betts will be up. That may sound like a whole lot of nothing to you, but those players currently stand to make about $90 million in 2019, which is almost half of the Red Sox’ payroll.

Here’s the problem: even if Kimbrel walks – and he will – you could certainly make the case that all of the remaining players are underpaid. Starting next fall, assuming health the fivesome of Bogaerts, Betts, Sale, Porcello and J.D. Martinez will be worth an average of more than $25 million per year on the open market, and there is no way the Red Sox will commit to all of those players for the length of time that will be required in those deals.

OK Mazz, so they’ll just let some of those guys go and replace them with prospects.

Good idea!

Except the Red Sox don’t have any. And before you claim this is merely manipulated information that has been put through the Felger & Mazz processor, think again.

Late in the season, Dombrowski admitted that the Red Sox farm system “has taken a hit.” He added that the organization is “trying to build our system back.” Following the World Series win, he noted that the Sox have a number of interest prospects reaching Double-A this year and suggested that good performances there will completely change outsiders’ perception of the Boston operation.

Of course, he’s right.

But what if those players don’t perform?

Yes, we’re being a little negative. But you’re missing the point. At the moment, the Red Sox have shown no ability to keep this core of major league players together beyond 2019. They have also shown no ability to replace any or all of them from within. And even if they could, the Sox would still be faced with the uncomfortable reality that some players from their list of projected free agents should probably be traded before the club is left holding the proverbial bag.

In the end, let there be no doubt: Dombrowski’s tenure in Boston so far has been a success. But the next year or two may very well be his legacy, because we all know what happened the last time the Red Sox won a World Series.

They fell apart.

You can hear Tony Massarotti weekdays from 2-6 p.m. EST on the Felger & Massarotti program. Follow him on Twitter @TonyMassarotti.