Boston Red Sox v Seattle Mariners

Now that it’s final, what should we make of the Red Sox-Dodgers mega deal?

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I’m still shaking my head at the Dodgers-Red Sox deal, which is now finalized. Among the things that wouldn’t have made sense to me if you told me about them this time yesterday:

  • I’m surprised that the Dodgers — whose owners just paid $2 billion for that team — took on $271 million in financial obligations and actually gave up real talent to boot.
  • Though I understand the Red Sox wanting to get rid of Beckett and Crawford, I’m surprised they actually did it. There has seemed to be so little consistency and coherence in that front office over the past two years I’m frankly shocked that a consensus to start over, more or less, was reached.
  • Heck, I’m surprised that someone decided that the deal had to include Nick Punto. Like, on that call, at some point, either Ned Colletti insisted that Nick Punto was a must-have or Ben Cherington decided that Punto and his $450K or so that he’s owed for the rest of the season had to be unloaded too.

But expectations flummoxed or not, it did happen, and it’s hard to see how this isn’t a win for the Red Sox. Albeit maybe not as big a win as some folks are making it out to be.

The winning part: A cleansing purge of Josh Beckett, who no one liked anymore and who seems to be a shadow of his former self. A liberating purge of Carl Crawford’s contract which, while it seemed like an overpay when it was signed before the 2011 season, has quickly turned into an all-out albatross given two years of injury and the realization that, no, he’s not gonna age as well as some thought.

And, of course, the acquisition of some young, promising players in Rubby De La Rosa, who — even if we should never put too much hope in any one pitching prospect — could be an ace one day, and Jerry Sands who may find Fenway to his liking and should have a greater chance to play on these new-look Sox. Throwing in Ivan DeJesus as depth and Allen Webster who, while maybe a year or two away, could definitely feature in the Sox rotation one day, and you have a lot of pieces for the next good Red Sox team. I don’t think James Loney is worth mentioning, but I’m sure he’s a nice fellow.

But let’s temper our expectations. Upside or not, none of the pieces coming back is a sure thing. De La Rosa could struggle with command as so many post-Tommy John pitchers do. Sands has been a creation of the Pacific Coast League so far, so he’ll have to prove himself.  But the biggest place to temper expectations should come in the financial relief the Red Sox received. Because while, sure, it’s awesome to have $50 million+ free a year going forward, it’s not like there’s a never-ending supply of talent to spend it on.

Teams are locking up young talent so early these days, leaving far fewer blue chippers to actually hit the market.  Matthew will take a look at this in greater depth later, but let’s quickly look at who’s available this offseason: Josh Hamilton. Zack Greinke. Robinson Cano. Jhonny Peralta. David Wright. Michael Bourn. Only two of them — Cano and Wright — are unequivocal game-changers, and those two are highly unlikely to actually be available when it’s all said and done. UPDATE: Er, scratch that. I forgot that Cano and Wright have team options, so that makes it worse. The other free agents have question marks or aren’t slam dunks. They’re all basically Carl Crawford, right? And the Sox are clearly repudiating the idea of signing the Carl Crawfords of the world right now.

So, you take that $50 million and plow it into player development, right? Well, some of it. The new collective bargaining agreement prohibits teams from doing that with any sort of gusto. Between the draft and international signings you can only spend a fraction of that money. So no, you can’t use that to really go crazy on either the free agency market or player development. At least not all at once.

Put differently: the Red Sox are retrenching for the long-haul, and the days of them being somehow exempt from the success cycle that every other team but the Yankees is subject to are over.  There’s a lot of talent on this team and a lot more flexibility now, but if you overhear any Red Sox fan saying, thank god, now the team can go out and sign some real free agents, you should feel free to ignore them.  Because there’s a better chance that the biggest short term upside of this deal for Boston are increased profit margins due to decreased labor costs as opposed to some quicky-re-load of a rebuild.  That doesn’t make it a bad deal for them — I think Boston won this trade — but it’s not like there isn’t risk about it all and it’s not like there aren’t some rough days still ahead.

Turning to the Dodgers: man, where is all of this money coming from?  I know the new ownership is flush with cash and/or credit — how can you pay $2 billion for the team if you’re not? — but they also just jacked their payroll up to the $190 million range for 2013. I know they have a new TV deal in the offing and I know the fans are coming back to Dodger Stadium now that Frank McCourt is gone, but this is not quite the money-printing market that, say, New York is. And even the Yankees have pushed their payroll down in recent years.

But the finances of it all are between Mark Walter, Magic Johnson, their silent partners and their gods. What’s it mean for the baseball side?  An improvement, sure, but not a dramatic one, necessarily. And, like Boston, there’s risk here, albeit risk of a different kind.

Carl Crawford won’t play this year. Josh Beckett and Adrian Gonzalez have each had down years, though Gonzalez has had a much better second half. Even assuming, however, that Gonzalez and Beckett suddenly take on vintage form, there are only 36 games left to play and they’re in a three-game hole in the west and a 1.5 game hole in the wild card. Sure, it’s possible that their addition pushes the Dodgers past San Francisco and/or the other wild card contenders, but it would take a hell of a month or so from them to do it.

The long-term is murkier. I feel like Adrian Gonzalez has several good years left in him and he may find himself rejuvenated to be back in the NL (and in his homeland of Southern California). Beckett and Crawford, however, are much shakier bets.

It’s hard to remember that Beckett is only a year removed from a season in which he put up a 2.89 ERA and a WHIP of 1.026, but that’s one year surrounded by two in which he looks like any old palooka, not the ace he once was. Nothing about him at this point suggests a pitcher who is going to age particularly well — Josh, it’s called a treadmill, please hit it — but it could happen. Crawford had Tommy John surgery just this week. I really have no idea what he’s going to be like going forward. Speed ages well and, assuming his arm isn’t toast after all of this, his defense will be a bigger plus in L.A. than it was in Boston. He could have a couple of All-Star years left in him or he could turn into Roberto Kelly.

The money here is the ultimate arbiter. If the Dodgers are like every other team in the history of baseball, they will not be able to absorb three gigantic contracts which correspond with only one elite player. There just is no way to eat that much cash and still field a consistently competitive team.  If, however, Beckett and Crawford find the fountain of youth, or if the Dodgers’ brass really has tapped into some crazy new revenue that we’re really not appreciating right now, it could all work out.

Going back and reading all of that it sounds like a bunch of negativity. I really don’t mean it to be. This deal is as exciting as all hell. It’s one of the biggest trades in baseball history, really, in terms of both big names and cash.  And with a trade so big it’s understandable that there are downsides for each side. No one ever completes a monster deal without some sort of risk or misgiving because, at the highest levels of business sophistication, no one truly gets suckered.

But on balance, if I had to say who won this one, I’d say it’s the Red Sox. Mostly because they now have far, far less to lose.

Athletics sign Santiago Casilla to two-year, $11 million deal

MIAMI, FL - AUGUST 10: Santiago Casilla #46 of the San Francisco Giants throws a pitch during the 9th inning against the Miami Marlins at Marlins Park on August 10, 2016 in Miami, Florida. (Photo by Eric Espada/Getty Images)
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After letting rumors of the deal percolate for the last week, the Athletics officially announced their two-year, $11 million contract with right-hander Santiago Casilla on Friday (and threw a little bit of shade at the Giants, too). As previously reported, the contract includes an extra $3 million in performance bonuses.

Casilla, 36, got his major league start with Oakland back in 2004, racking up a 5.11 ERA and four saves over six seasons in the A’s bullpen. After picking up a minor league deal with the Giants in 2010, the righty flitted in and out of the closing role with varying degrees of success. Notwithstanding a slight downturn in his production rate during the 2016 season, he earned 123 saves and a 2.42 ERA during the past seven years in San Francisco. Securing another closing role might be a little tougher across the Bay, however, with a bullpen that includes fellow closers Ryan Madson, Ryan Dull and Sean Doolittle.

Keith Law: The Braves have the best farm system. Who has the worst?

PHOENIX, AZ - APRIL 06:  General manager Dave Stewart of the Arizona Diamondbacks laughs on the field before the Opening Day MLB game against the San Francisco Giants at Chase Field on April 6, 2015 in Phoenix, Arizona.  (Photo by Christian Petersen/Getty Images)
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Why is this man smiling? Man, I wouldn’t be smiling if I read what I just read.

This is the week when ESPN’s Keith Law releases his prospect and farm system rankings. He kicks off his content this week with a top-to-bottom ranking of all 30 farm systems. As a rule he limits his analysis to players who are currently in the minors and who have not yet exhausted their rookie of the year eligibility.

For the second straight year, Law ranks the Braves as the best system in baseball. Number two — making a big leap from last year’s number 13 ranking – is the New York Yankees. Dead last: the Arizona Diamondbacks, which Law says “Dave Stewart ritually disemboweled” over the past two years. That’s gotta hurt.

If you want to know the reasons and the rankings of everyone in between you’ll have to get an ESPN Insider subscription. Sorry, I know everyone hates to pay for content on the Internet, but Keith and others who do this kind of work put a lot of damn work into it and this is what pays their bills. I typically don’t like to pay for content myself, but I do pay for an ESPN Insider subscription. It’s worth it for Law’s work alone.