Shower drain leaking badly

Shower drain out of nowhere started leaking around the drain. Popped off the grate and puzzled at what I am seeing. Must confess I really never paid attention when I cleaned this thing out a few times.
There is like a tan rubber threaded insert at the top of the drain that seems a bit bent up. What confuses me is it feels like something was remove as the threads don't do anything. Accused my wife and she denied it (you know how that goes)
Here is a picture: http://ctrlv.in/454290
If you can give me some guidance I'd be grateful.
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Tim,
What's leaking? Is it pipe? A pipe connection? The drain to shower floor connection? I've no idea what the rubber threadd insert does but I'd guess that it holds the grate that you popped off.
Dave M.
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wrote:

No thread, nothing is supposed to be in there.
What you see is a molded rubber insert that is force fitted between the plastic grain pipe and the shower pan.
I don't know how easily removed it would be. It is probably 2 or 3 inches deep and is a bit tough to pull out. I'd clean it well, let it dry, then silicone around the OD and ID and let it set for about 24 hours.
Not sure why it is bent in either. It looks like the drain pipe was cut a little too short when it was installed. The pipe and the insert should be about even at the top. My guess is, over the years, the rubber dried out a bit and started to shrink in at the top and now the water gets in there, puddles, then leaks. Fill it to the top with the silicone so water runs across it and down the drain.
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