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By Tony Massarotti

BOSTON (CBS) — Make of this what you will, but Bleacher Report recently offered its latest assessment of the farm systems of all 30 teams in major league baseball. The good news? The Red Sox are 16th, which is higher than some thought they’d be.

The bad news? They dropped there all the way from fourth.

What all of this reaffirms is that the Red Sox had better win a championship in the next three seasons because what happens after that is anybody’s guess.

The Chris Sale deal? Of course it was worth it. In acquiring Sale, the Red Sox gave up three prospects deemed to be in the top 10 in their organization, including Yoan Moncada (No. 1 overall in all of Major League Baseball) and Michael Kopech. That is hardly the problem. The problem is that Dave Dombrowski did so after deals that felt like overpayments for left-hander Drew Pomeranz and right-hander Tyler Thornburg, the former of whom has been underwhelming as a starter since joining the Red Sox (predictable) and the latter of whom has a right elbow that feels like a time bomb.

Here’s the point: if Red Sox president of baseball operations Dave Dombrowski had shown a little more discretion in acquiring Pomeranz, he might have been able to save himself someone like right-hander Anderson Espinoza, which he might have been able to include in the Sale (or some other trade) at the expense of another prospect. Get the idea? One of Dombrowski’s strengths is that he is decisive and acts quickly. At the same time, that suggests he doesn’t spend much time negotiating.

So he pays the price. And moves on.

Here’s the bigger point: Dombrowski seems to scoff at the notion that he prefers established veterans, though his resume is now littered with examples of him possessing a win-now mentality. The 1997 Florida Marlins bought a world championship, after all – and there’s nothing wrong with that – but the Detroit Tigers ultimately failed under Dombrowski’s leadership. The Tigers now have the 26th ranked player development operation in the game, all but forcing them into a tear-down mode.

Dombrowski doesn’t like the perception that he is too willingly sacrifices prospects, but the history is what it is.

“It doesn’t really matter if it’s fair or not,” he told me roughly a year ago. “If you look at my career, you’d see that when I was in Montreal we were very developmentally oriented. We went to Florida and we were also developmentally oriented. We went to Detroit and we were in a win-now mode—that’s where we were as an organization…. The reality is I love young players. To me, the core of young players we have here at the major league level is exceptional.”

To be fair, Dombrowski has kept Mookie Betts, Jackie Bradley, Xander Bogaerts and others, including Blake Swihart. Overall, the Red Sox have a good, young core of positional players. Just the same, that core will basically reach free agency in three years, and the team’s ability to sign all of them is in at least some doubt. (Bradley and Bogaerts are represented by Scott Boras, who usually takes his players to the open market.)

All of that suggests the Sox are at least a little overleveraged at the moment, a fact illustrated here. Of Boston’s top 10 “prospects” according to Bleacher Report, one is Andrew Benintendi, who is actually the projected starting left fielder on the big league team. Of the remaining nine, six are in A-ball, which by definition makes them borderline at best.

Andrew Benintendi rounds the bases after hitting a home run against the Cleveland Indians during game one of the ALDS on October 6, 2016. (Photo by Maddie Meyer/Getty Images)

Andrew Benintendi rounds the bases after hitting a home run against the Cleveland Indians during game one of the ALDS on October 6, 2016. (Photo by Maddie Meyer/Getty Images)

Look, you’re a fan, so we get it: you want to win now. You’ll deal with 2020 when it comes. But the fact is that the Red Sox have the resources and organizational cachet to be both a big spender and a player development factory. They should be both. It certainly feels like Dombrowski has tipped the scales too far toward the short term, and it feels like everybody in baseball knows.

If the Red Sox win a World Series in the next three years, well, it will all be worth it.

But if they don’t, then prepare yourselves to become the Detroit Tigers.

 

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