Sunday Mail: Should the Red Sox Trade Their Best Prospects Before Their Flaws Can Be Exposed?

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Hello and welcome to today’s Reader’s Digest condensed edition of Sunday Mail. We’re going baseball-only since all of the Patriots questions will be obsolete after today’s Bills matchup and the best of the Celtics, Bruins and media questions were answered in the chat.

Also, in case you missed it, here’s my longer Sunday piece on Bill Belichick, Chuck Noll, Bill Walsh, and what happens when a successful coach ages. The game won’t pass him by — though today’s particular game makes me nervous.

On to …

THE MAILBOX

Will the Red Sox start trading AA talent to get more value before they come up so they don’t expose their foibles at the major league level?
— Tatupu

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Unilaterally? In a vacuum? Well, no. Of course not. That would be foolish. I understand the genesis of this question — it’s because Xander Bogaerts and Jackie Bradley Jr. failed to meet their massive expectations this season, and Will Middlebrooks continued to regress. But generalizing — hurry, trade all alleged prospects before they fail! — would be a brutal approach to building a roster. Young, cost-controlled talent is essential to even the rich teams, and the notion that they need to get rid of them before they are exposed is the wrong way of looking at it. Many of them will make it — I’m convinced Bogaerts will be everything we thought he was last October, Mookie Betts looks like a potential cornerstone, Blake Swihart and Henry Owens are among the best prospects at their respective positions, and so on. Some won’t. The key is sorting out the keepers — like the Sox did with Dustin Pedroia, Jacoby Ellsbury, and Jon Lester a decade ago — from those whom the organization believes are expendable.

Hey Chad– I respect your thoughts on the Sox and tend to agree about 95% of the time. But, and please hear me out… don’t you think the current regime, while certainly deserving of credit for the 2013 championship, is deserving of some skepticism for: (1) grossly overestimating the ’14 contributions of Middlebrooks, Bradley, and Bogaerts, (2) failing to sign Lester, (3) a long-term extension for a certain 2B with declining power and questionable health, and (4) the possibility of fielding a team with 3-4 rookie starters–maybe more–next year? I think Cherington is smart and I do like the young guys we have, but you seem to put a rosy picture on these Sox considering they just lost 90 games for the 2nd time in 3 years. At the very least, don’t disparage those of us who, while certainly rooting for a return to the playoffs in ’15, are a bit tempered in our enthusiasm and don’t blindly trust that the right moves will be made. Thanks.
— Realist

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More than fair, Realist. My problem is never with those like you who are a bit tempered in their enthusiasm. They should be. I should be (and, generally, I am, though I think my positive approach gets exaggerated because it’s such a contrast to that of some writers with whom I work. My beef is with the people who constantly bleat about the worst-case scenarios. You cannot shrug off what happened in ’13 as an aberration. Championships in baseball are too damn hard to win, too much of a grind, too dependent on both talent, intelligence, and good timing, to be aberrations. I agree with you that there is a lot to sort out before next season, and I’ll admit I’m not sure how Cherington is going to approach it in terms of making next year’s team a contender; there are more variables with this roster than I can ever recall. It’s why this offseason is both fascinating and crucial, and I think we’ll have a far more accurate evaluation of Cherington as a general manager after next season.

Are we allowed to cheer against the Orioles because of Dan Duquette?
— ChadusPhD

I’m cheering against them, but not for that reason. The Royals have a chance to be one of the best sports stories in recent years. How can you not root for them? Besides, I’m someone who grew up rooting for George Brett, admiring how different the speedy Royals were from the Red Sox, and feeling a kinship with them because the Yankees so often ruined their dreams. As far as Duquette is concerned, I’m happy for him. He should have been back in baseball long before he was, but it seems the absence did humble him a little bit. There’s some revisionist history on what he actually accomplished here, mostly driven by those who want to discredit Theo Epstein for some reason, but he was a pretty good general manager. Hard to have a beef with the guy who brought Manny, Pedro, Jason Varitek, Johnny Damon and Arquimedez Pozo to Boston, though his flaws (too many scrap-heap guys in crucial spots, an often barren farm system) also must be part of the assessment. When Duquette got the Orioles gig, I wrote this deep-dive assessment of his time in Boston if you’re interested in such things.

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Until next week, the mailbox is closed. Exit music, please.

Remote stalled on this while I was flipping channels last night. Loved it instantly. She’s Donna Summer’s daughter, by the way. There’s always something worth hearing on Live From Darryl’s House.

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