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This was the purpose of my post over at MarinerCentral "Process vs. Outcomes".  Almost all trades appear defensible on the surface and this is why the 'moron' and 'idiot' labels say more about the commenter than the commentee.  This doesn't change the fact that Bavasi, judged dispassionately, failed and failed quite severely.
But you say why is the tough question, and my answer is that the difference between success and failure for GMs is sufficiently narrow that the only way to fairly and accurately answer the why question would require a full post mortem on the circumstances and details the situation.
Why did he make the Cabrera for Perez deal -- in my mind one of his two worst trades, the other being Soriano for Ramirez?  Was it external or internal pressure?  Did he underestimate Cabrera?  Overestimate Perez?  Overestimate the M's odds?  Think if we still had Cabrera?  We could have traded Betancourt when he had value.  We wouldn't have to invest $8M in Wilson... and on and on...
You ask the right question, but a fan can't answer it.