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What was THE moment you knew the Astros were headed towards disaster?

There are moments in my life I will never forget. One of those moments is watching Orlando Palmerio get thrown out at first base to end Game Four of the 2005 World Series. I watched the game with Evan, and few other bandwagon-y college friends, in Evan's apartment. As crushing as the moment was, Evan and I began to talk about next year within ten to twenty minutes (every baseball fan's perennial best friend).

You all know the story from there; it is not pretty. Aside from 2006 and 2008, sub .500 has been the name of the game. Even in 2006 and 2008, I spent large stretches of the season contemplating what the Astros needed to do to right the ship in their next season.

I recently have spent the last month under a rock. The last substantive piece of Astros news I have tried to really think through is the Paulino trade. Other than that, my energies and focus have been elsewhere. In lieu of dissecting relative Astros news, the part of my brian that has been conditioned to contemplate the Astros had to compensate. Its compensation has been tracing back my Astros thinking to the moment it became apparent to me that things were headed to a five to seven year stretch of near, if not below, mediocrity.

I have tried this thought experiment several ways. I have started from Orlando Palmerio's pinch hit at bat and moved forward. I have started from Felipe Paulino's trade and moved backwards. I have plotted out the major signings, trades, and drafts of the last few years. None, of it though, has taken me to a moment, game, personel move, etc. where something clicked in my head and I knew that things were going to get much worse before they got better.

The closest I have come is April and May of 2007 when Hunter Pence was setting the PCL on fire and Chris Burke was playing below replacement level baseball. The Astros front office kept reiterating that it was about rewarding veteran experience, etc. It's the first time I can remember prophesying doom. But I am not sure that is really when it clicked for me. It might have been that year's draft. But even still I think I kept clinging to the feeling I had in October in 2005.

The moment where I think I finally was ready to view the bleakness of the Astros current and future state probably came in the Winter of 2008, when Ty Wigginton was non-tendered. There was something about the absurdity of then being forced to call on Geoff Blum's services to save $4 million because there was likely no relief coming from the farm system that made it fully click with me—the Astros were screwed.

I doubt that is it, either. But I'll keep working at it. 

I know that this is kind of a depressing topic. And I know that the last two days have been about Christmas spirit and hopeful wishes. I'm sorry to crash that party. But until I get myself fully briefed and focused on the Astros, I'll likely following this mental rabbit trial. Instead of making this a solo trip, I wanted to see what moment, personel move, etc. everyone else points to.

Hopefully tomorrow there will be something less morose to discuss.