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I have just always assumed that it was caused buy damage that was being inflicted. I would imagine it would take a smooth character to have that kind of cool to drop the gear while having the plane shot out from under me.
There's also the possibility of it being used as an airbrake, slowing the aircraft so there's less chance of hitting the fin/tailplane when departing.
Gymbyk is 100% correct. some aircraft will even have uplocks that are hydraulically engaged, lose pressure anywhere in the system and the uplocks will disengage, gear will come down.
I read of one German Bomber that lowered the wheels as a sign of surrender over the North Sea.
see the first clip
P.S. what part of long island are you from? I'm originally from Queens but lived in Roslyn for a few years before moving down south.