OT: Is Brian Cashman Overrated?

In Friday's Open Off-Topic Thread, timlacy started a thread asking whether or not Brian Cashman was overrated.

I took the stance that he was, which drew a cyber eye-roll from Matt Klaassen (née* devil_fingers). As I stated in my response, I will gladly defer to Matt in general (one of us writes for FanGraphs; one of us does not), but then the discussion died. Am I off-base for believing Brian Cashman to be overrated?

*I'm aware that this is the feminine past participle of naitre in French, but I'm using the second definition - formerly known as - and simply do not know French to be able to conjugate this into a masculine form.

Admittedly, it is generally unpopular within this forum to come down on the same side as timlacy (and I'm not entirely sure that our respective rationales for believing this are coming from the place). This is clearly the first sign that I might be in the wrong on this issue. It is also obvious that given their respective situations, Brian Cashman is the better General Manager than Dayton Moore. He has a World Series Champions banner hanging in Yankee Stadium: The Squeakquel with a roster that is mostly his creation (Derek Jeter, Jorge Posada, and Mariano Rivera were all holdovers from a different GM, but Cashman did retain their services). 

After billybeingbilly's statement that the Yankees' system is "very good now," I posited the questions

How much of that is the hype-machine? How much of it is the Yankees FO misrepresenting information to drive up the value of their prospects?

I know this can sound like the insane musings of a crippled conspiracy theorist, and it did receive a dismissive "oh boy" from Mr. Klaassen to which I responded:

I'll gladly defer to you, but am I that far off? Cashman’s been in control since fall of 1998. What has their system produced in 12 years of limitless resources?

Do they not misrepresent information to their benefit? All teams do it to a degree, stating that Pitcher A was throwing x mph when really that pitcher was throwing x – 3 mph. Are the Yankees not known for this?

I have heard that the latter point is the case in regards to the Yankees, at least in passing. I admit I am no more in the know than most people here, but given the hype surrounding so many of the Yankees prospects that is left unrealized, the basis for such thinking would seem to be there.

Obviously, somewhere between a little bit and most of the hype that many of the Yankees top prospects get can be chalked up to the media market that they play in, but I've heard people who know a lot more than I do toss around the idea that the Yankees practice this to inflate the value of their prospects. Other teams do this, too. It is smart business practice, especially if that player can be turned around based on this misinformation. The memories of most fans are short enough that these lies can generally be assumed to have been forgotten after awhile anyway. I know there was a prospect this year from another team who saw his status rise on a prospect expert's list because of such an exaggeration. 

With regards to their system, my analysis (if you can call it that) is admittedly superficial. And, as Matt noted in response to this comment (snarkily - appropriate for RR, I suppose), I overlooked Brett Gardner (but not Robinson Cano). I think the points that follow have some verity to them.

Honestly, I would argue that they can always afford to overpay for both Latin American amateur talent and guys with signability concerns, yet just on a gut level, the system doesn’t seem to produce much Major League talent. The hype machine blows the prospects up, but if we go back to 1999 and look at what they have produced, it is relatively insubstantial considering the limitless resources.

And, yes, they have always been drafting at the end of the first round, but that disadvantage is at least mostly negated by how much money they can spend in Latin America. Even the pieces they have traded off at the deadline have been mostly unimpressive.

When a system with seemingly limitless resources has churned out only Robinson Cano insofar as top talent is concerned, there might be a shortcoming. Sure, [Phil] Hughes seems to show promise (his first half of 2010 was a mirage), but Joba [Chamberlain] has been pretty uninspiring. Of the guys they’ve traded, maybe [Jose] Tabata will be good, Austin Jackson is not nearly as good as he appeared to be last year, and then you have to go back to Ted Lilly, who they traded for after he’d already made it to the Majors or Jake Westbrook who had already pitched in Double-A when they acquired him from Montreal and then shipped off to Cleveland in the David Justice deal.

I’d even argue that his free agent acquisition skills are overrated.

When made aware that I had omitted Gardner, I stated

Admittedly I forgot to mention Gardner, but to be honest I kind of hate him, and he has produced for a year and a half. Much of that value is from his defense, as well.

My main issue with the sh**bag is the fact that sliding into first to beat out a single is asinine, yet everyone fellated him for it in the playoffs. Multiple times. Grit factor. Lame.

Apologies for some of the language therein, I censored the curse word for the faint of heart. Almost all of Gardner's value is from his defense, and that defense is in left field, the second least important position on the field. He is a very, very good defensive left fielder, though.

In regards to the free agent acquisition skills, or lack thereof, Cashman has been playing with house money and a stacked deck (and a bunch of other hackneyed cliches indicating an unfair advantage). With this in his favor, he has handed out horrible contracts to the likes of Javier Vazquez, Carl Pavano, and A.J. Burnett (which I wrote about at length when it was inked here). In the latter two instances, the deals seemed bad when they were inked. More importantly, even the contracts that they hand out to vets who pan out initially are immovable albatrosses by the last few years of the deals.

The real problem to me is that they are playing with a largely broken business model. They outspend every other team by at least $50MM. Even with chance coming into play, when your payroll is at least 1.33 times higher than your next closest opponent, the expectation of winning should expectantly be higher, and the one World Series trophy in the last ten years really is not enough.

The reason this is the case is that their team has been comprised of not just mercenaries but aging veterans on the decline from their peak phase. By the time nearly every player on the roster is donning pinstripes, they have likely already played their best season. Maybe there is less uncertainty with these players, as they have definitely already produced on the Major League level (otherwise the Yankees would not be offering insane contracts to them), but they are also more than likely going to be producing less than the average player who is in his third to sixth season in the Majors.

Maybe I'm off-base here, and I welcome everybody's criticism. Also, I apologize for copying so much from the comments section of another FanPost, especially if you already read and dismissed it. Normally, I would have just posted this at my blog (shameless plug), but it seemed like this was the most likely place for it to get read and receive feedback. Furthermore, I haven't been religiously reading every FanPost, FanShot, and Comment, so maybe this has already been covered ad nauseum - if so, I apologize for that as well.

So, readers: Am I wrong? Is Brian Cashman either properly rated or underrated? Am I insane and blinded from an objective standpoint regarding the Evil Empire?