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I'm probably too subjective on this one.  But when the M's acquired Randy, that was pretty much franchise-altering, yeah?  Not sure it received its proper celebration, but that heralded the beginning of a real franchise for the area.
Weren't Sabathia and Burnett signed during the same 24 hour period?  That's gotta rank up there, even though it doesn't appear to have involved historically great pitchers, just very good ones going to a team that more than desperately needed them.
But for your division rival to lose their Ace to their number one most hated enemy, and to lose out on their prime replacement target is pretty bad.  That their intra-division rivals end up getting a 1a starter as a direct result of them losing out on their prime target...yeah, that's probably as much of a gutpunch as you can draw up.