Filip Bondy looks at Brian Cashman today:

Despite all the solid moves Cashman has made over the years involving position players, he has done nothing to convince anybody that he knows much about starting pitching.

His resume is littered with mistakes on this front, from Jeff Weaver to Kevin Brown to Carl Pavano. This is not an uncommon affliction among major league executives, because the rotation is a mysterious and nuanced thing. It is far easier to predict the near and distant futures of position players, and even those of closers, than those of starters.

But over a long period of time, patterns of organizational success and failure emerge and they determine whether a team wins its share of titles. During this millennium, the Yankees are chronic losers on this front.

Picking from the same talent pool and with similar resources, the Red Sox somehow acquired the better ex-Marlin (Josh Beckett vs. Pavano), the better ex-Diamondback (Curt Schilling vs. Randy Johnson) and the better ex-Japanese star (Daisuke Matsuzaka vs. Kei Igawa).

Over recent seasons, the Chicago White Sox won a title on arms from the Yankees’ discard pile, while a trio of teams – Oakland, Toronto and the Cubs – squeezed nearly a thousand solid innings from Ted Lilly.

Some of these mistakes can be laid on the doorstep of the old, bumbling Tampa brain trust, a dysfunctional collective. But Cashman took direct control of the team at the close of the 2005 season, when he signed that three-year, $5.5 million contract and said, directly, “I’m the general manager, and everybody within the baseball operations department reports to me.”

By then, Chien-Ming Wang, the team’s one and only true prize, was already signed and showing great promise. Cashman re-signed Andy Pettitte, a strong move. He re-signed Mike Mussina, a so-so move. He re-signed Roger Clemens last May to an $18 million contract, a wrongheaded move announced at the time with great fanfare.

He can’t lay off these transactions anymore. And in the end, he will be graded on his decision to snub Santana while grabbing tight to the futures of Hughes and Kennedy. Expect a divisive debate about that issue for some time, because these pitchers are just 21 and 23 years old, respectively.

Cashman is very much on the spot, and that spot is the mound. If the kids don’t come through, if Santana keeps throwing like this at Shea, Cashman may find himself out of the rotation – like too many of his acquisitions.

You know what’s amazing? One year ago – to the exact day! – on May 6, 2007, Joel Sherman wrote, basically, the same article on Cashman:

Cashman is going to be judged on starting pitching, where he has rightly spent the most energy and money. His refusal to trade pitching prospects and his fixation in the last draft on adding the best arms regardless of cost has been met with universal approval around the game. But Cashman’s history with starting pitching is mixed, at best.

Cashman has hardly authored every questionable decision of the last decade. For example, he either was against or had little input in obtaining Randy Johnson, Jaret Wright and Jose Contreras. But he certainly was out front on Javier Vazquez, Jeff Weaver, Kevin Brown and Carl Pavano even before he was given sovereignty over baseball decisions.

The misses on Vazquez, Weaver and Pavano were dramatic. All were prime-age arms who were supposed to sustain the Yanks for years. Vazquez and Weaver cost young talent that might have been better directed elsewhere. The Yanks, for example, used Nick Johnson to obtain Vazquez rather than Curt Schilling, who instead went to the Red Sox and helped Boston end The Curse. Weaver cost Ted Lilly, who proved capable of pitching in the AL East. The Yanks then compounded misery by turning Weaver into a bigger mistake in Brown. And Pavano has been subtraction by addition, failing to get on the mound and hurting clubhouse morale.

Cashman details that many teams were after Vazquez, Weaver and Pavano. Which is true. But you are not judged by what others might have done, only what you do.

So it is even more imperative that pitching decisions from this group that look problematic now – signing Kei Igawa, spurning Lilly and Gil Meche, making what ultimately was a tepid offer for Daisuke Matsuzaka, believing in the youngsters within the system – ultimately look better in the long run.

In addition, Cashman traded Gary Sheffield and Randy Johnson in the offseason with the main haul being Humberto Sanchez and Ross Ohlendorf, supposedly high-caliber arms who could be stashed at Triple-A for an emergency. Well emergency has struck. Matt DeSalvo goes tomorrow, a record 10th starter needed by one team in the first 30 games. But none of them is Sanchez or Ohlendorf.

Sanchez, who another GM said “had too many red flags to acquire because of his injury history,” already is out with Tommy John surgery. The Yankees could have taken a lesser overall package from Arizona and obtained Micah Owings, who has a 3.38 ERA in four starts for Arizona. Instead, they took Ohlendorf, who has been so abysmal at Triple-A that DeSalvo, Phil Hughes, Chase Wright, Darrell Rasner and Jeff Karstens have all gotten opportunity instead of him.

Cashman said the organization was aware of Sanchez’s elbow troubles, but still viewed him as a long-term asset even if surgery were needed. He also said he has not lost faith in Ohlendorf. The Sheffield deal to Detroit for Sanchez, Kevin Whelan and Anthony Claggett represented the second time Cashman has made a three-pitchers-for-one-hitter trade with Tigers GM Dave Dombrowski. In February 1999, when Dombrowski was running the Marlins, the Yanks dealt Mike Lowell for Ed Yarnall, Todd Noel and Mark Johnson, under the belief they had restocked their system with pitching. All three were busts. Cashman cannot have that repeat.

Well, as many know, for the last 16 months, I have been not shy about questioning Cashman’s track record on selecting pitching.

And, in the past year, from Sherman to Bondy, the mainstream media has picked up on this as well now.

Sooner or later, this school of thought is going to pick up more and more steam. And, at some point, it will spell the end of the Brian Cashman era in Yankees history.