Brian Cashman's Back: Let's Look at His Legacy

Erik DianaCorrespondent IOctober 8, 2008

So, Brian Cashman is back. He's back for another three-year giddy up in the Bronx. He's back to finish what he started, and he's back to clean up a mess that he's largely not responsible for either. Needless to say, the pressure is on Cashman now.

Cashman staked his legacy of the last 10 years to Phil Hughes, Ian Kennedy, and Joba Chamberlain this season. He put his neck on the line in the hiring of a manager that seemed oblivious on how to help his team score runs and how to handle the media.

The story for Cashman does not start in 1998, when he first became the caretaker of the Yankee dynasty. The story really begins in 2005, when Cashman was dead set to walk away.

Cashman was finished! He grew weary of George Steinbrenner. He was fed up with George's dictatorial influence and the fractured organization his micromanaging had wrought.

At this time, the Yankees were years behind Boston, Cleveland, Minnesota, and Tampa Bay in player development. They were old, slow, and broken. The payroll was bloated and it grew obvious that they just needed to blow the whole organization up and start over.

Cashman knew that with the way the Yankees were run and being run, that it would make much more sense to walk away with his dignity intact.

But something changed dramatically. George Steinbrenner, whose role with the Yankees became convoluted because of health reasons, actually ceded power over to Cashman. Cashman, for as smart as he is, had Steinbrenner sign to the agreement in writing so he could keep his word.

More than anything, Cashman wanted the Yankees to get loaded with blue-chip prospects. He wanted to rebuild the farm system to not only be able to call on a stud prospect at any time, but he wanted a freshly stocked farm system to be able to use for trade bait, just in case he needed it.

What a lot of people forget is that the Yankees were drooling over Carlos Beltran and Randy Johnson in the summer of 2004 but had no way to get them onto their roster. Because the team's farm system was so depleted and payroll was so high, they had to choose between Beltran and "The Big Unit" again in the winter of 2004 and the start of 2005 season, because both would have been too expensive.

They chose Randy Johnson, who would up winning 34 games for the Yankees but had a rough go with the press and in the postseason. In the end, Randy Johnson asked to be let out of New York after he was practically useless in the 2006 playoffs with a bad back.

People will always ponder to themselves that the Red Sox may not have had their amazing comeback if the Yankees would have had the prospects to snag both of these players in the 2004 season. Because of Steinbrenner’s paradigm, he was mostly to blame for the fact that the Yankees couldn't have these players. The Yankees continually robbed Peter to pay Paul.

Cashman's first run with using prospects came in the summer of 2005 when Robinson Cano and Wang were called upon to help save the sinking ship that was the Yankees team. They played well for the most part.

The Yankees eventually made the playoffs because of Wang and Cano. Also, they found life in Aaron Small and Shawn Chacon spinning gems on a consistent basis as well.

Also, what shocked Cashman was the fact that Yankee fans, who are impatient to the point of being moronic a lot the times, actually gave the younger players a lot more time to develop than they would a big free-agent signing like a Jason Giambi or Carl Pavano. Even typical Yankees fans were smart enough to let these young kids have a shot and see if they would sink or swim.

(A typical Yankees fan is someone who thinks that they should always go after the big name, no matter the cost or how pragmatic their thoughts are. Jack-O, who is on the B.S. report will Bill Simmons, seems to embody a typical Yankees fan!)

Through Cashman's influence, the Yankees changed their paradigm and formed a linear chain of command, at which he sat at the top. He alone, not anyone else, would report to George Steinbrenner. Scouts, pitching gurus, player-development people, and others in the organization would report directly to Cashman. Cashman alone would have Steinbrenner's ear.

So how has Cashman done with his overhaul of the organization? Really, we can't say yet! Honestly, Cashman got killed this year, fairly or unfairly, for not dealing Phil Hughes, Ian Kennedy, and Melky Cabrera for Johan Santana.

Cashman was not comfortable giving up Kennedy and Hughes, when their stocks were soaring up, to the Twins for Santana and then paying him a record-setting contract. He also had an ally in Hal Steinbrenner (the much smarter and shrewder of the Steinbrenner boys) and had a dissenting voice in Hank Steinbrenner (the buffoonish oldest son of George Steinbrenner who doesn't attend games and hardly ever goes to New York.)

Through Cashman's influence and ideas, the Yankees' season was saved in 2005 and sustained in 2007 through Joba Chamberlain. If the Yankees had their previous paradigm, they may have never drafted Chamberlain.

Cashman hasn't done a lot of things yet. He hasn't developed one stud starting pitcher. He hasn't drafted one unreal infielder or outfield prospect that will change the Yankees instantly. And no, Cano is not one of these can't-miss players anymore. He looks compromised as of right now!

So, all in all, Cashman's legacy is incomplete. The teams of the late 1990s and early 2000s were set enough for the most part that Cashman just needed to sign free agents and pull the triggers on trades that would help the Yankees. (Which he did in 2000, the Yankees don't sniff the World Series that year if they didn't overhaul their roster with the likes of David Justice etc.)

Cashman still needs time to develop his plan for the organization. If the Yankees miss the playoffs for the next three years and seem to be getting worse and have more poor drafts like they did this year, then by all means Cashman has to go. And this is a very real possibility because of the beast that now resides in Tampa Bay!

It's just hard to compare Cashman to Theo Epstein right now because Cashman is just finally able to wield his power that he was given a few years ago. Yankees fans need to get over the fact they didn't land Santana. Cashman was protective of his draftees and that's admirable. There are much worse things than the Yankees missing the playoffs! Plus, the real ramifications of this deal shouldn't even be discussed for another three years!

Now that Cashman has more time to implement his plan, it'll be interesting to see how the Yankees' makeup and philosophy will change. Now that Cashman has the time, he really is writing his own legacy!