Any idea why this shift shaft seal would be leaking?

Trans work sucks. No matter how long you drain the trans fluid, there will be 1 cup left under the valve body and no amount of pans will catch all the drips. At least that is what Ive found. The drips seem to travel to all points of the compass and drop right outside the catch pans footprint. Whomever created the trans pan with the drain plug deserves a beer. I would have tapped that seal in flush before changing it out. May have been a 5 minutes job with a deep socket on top and a crowbar forcing it down or C-clamp if you got one that ballsey.
Well it can still happen. Cuz the way it looks in the pictures is the way it still sits. All I had time for was to get things disassembled. And it took me way longer than 5 minutes just to get the damn linkages and levers off. LOL
But the way I'm looking at it is, I have to press one back on anyway. It might as well be a new one. Might try to run it if I knew how long it had been on there. I have no idea.
And yes I I like a trans pan with a drain plug, too.