“The Higher the Tree the Monkey Climbs, the More You See of His Ass.”

180189_1622106836134_1340340132_31665111_7128923_nThese words of wisdom were spoken by Brian Cashman at a WFAN event earlier this week when reflecting on his job as Yankees GM. It was fascinating to me to see first hand how some of his words at that event about Derek Jeter have now taken on a life of their own.

I had the opportunity to hear him speak to a small group and hold his ring (no, I did not kiss it) . Is it real or Diamonique? ( I think real). I came away with several impressions from the event:

1. He is very intelligent

2. He is passionate about his job and likes it.

3. He is a straight shooter. He does not “sugar coat” issues. He said he doesn’t try to be Mr. Popularity since he has to deal with serious business issues.

4. He has many egos to handle, his bosses, players, front office personnel. While he is the GM and makes most of the baseball decisions, it is not always his decision, and he is not embarrassed to say when he was overruled.

I think Brian Cashman has a great job, is doing a great job, but has an incredibly tough job. On the last point, the average fan might say, “He has an almost limitless budget, how hard can it be?” It is VERY hard, because, given the level of spending, the bar is very high. In fact, when you are 27-time Champions, the bar for the NY Yankees is a World Championship. There are no banners for the 13 Pennant winners which fell short or, worse yet, times when they didn’t reach the Series.

There’s also the reality that money doesn’t solve every problem. The Yankees have made many great player acquisitions and several poor ones. It’s nice to have the money to fix mistakes, but it hurts to make errors. I’m pleased that they have placed greater emphasis on their farm system. Though now a lifetime ago, the “Core Four”—Jeter, Rivera, Pettitte, Posada—were products of their system. And their farm system is now ranked 5th of the 30 teams, with 3 of the top 50 baseball prospects. In past years the farm system merely supplied talent to grease trades. This may still be the case to some extent, but for an older team like the Yankees, having younger future stars is critical to maintain their excellence.

One of the difficulties of Cashman’s job is handling older stars on the back nine of their careers. Handling Bernie William’s departure was difficult. The Yankees decided not to bring back Matsui and Damon despite the 2009 World Series heroics. And though each of the situations is different, dealing with the aging of the Core Four is a task.

Probably the most difficult issue is their iconic shortstop, Yankees Captain Derek Jeter. The difficult negotiations on his recent contract magnified this issue. Jeter is an all-time baseball and Yankee great, a first ballot Hall-of-Famer who will reach 3,000 hits this season and who has been part of five World Champion teams. Jeter has been a great talent and team leader, but he is also getting older, and will be 37 in June. He still ably plays shortstop and makes the smart play at bat and in the field almost ever time. But the question is whether age is “catching up”. A career .314 hitter, he hit a career-low .270 last year (and it took a September rally to do so). Is this a sign of decline, or merely an off year? We’ll see. He remains a terrific fielder but is often criticized for having lesser range, a critical element of a shortstop’s responsibilities.

So here’s where Brian Cashman’s butt was exposed, so to speak, at the WFAN event. He was asked a question from the audience about the possible future move of Jeter to third base. He answered honestly that he views third base as a “power position” and Jeter’s more modest power production would not be ideal, and that he could envision Jeter as an outfielder if a move from shortstop was ever made. He could have given a mealy-mouth answer “We’ll look at all the options if the time comes etc.” but in his candor combined with the fact that as GM of the Yankees he is the monkey that has climbed the highest tree, a story of Jeter’s move to the outfield was born– ESPN reports, sports radio chatter, etc. I was glad I was there to see the comment first hand and view the subsequent maelstrom. He also said when asked about comparing the Red Sox to the Yankees that the Sox have a better lineup at the moment given their better starting pitching. I was surprised that a comment like that didn’t have bigger impact than the Jeter comment. But the experience gave me a deeper appreciation of the difficulty of the job, and how off handed comments can take on a life of their own.

But hey, that’s life in the jungle when you climb the highest tree.  None higher than the New York Yankees. #28 in 2011.

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