Re: Not Good!
Well, it might be nice to know just what make and model you are working on.
Were the gaskets under the Vent and Drain plugs new and fresh? They MUST be replaced after EVERY service.
Finish the draining; install the plugs with new gaskets and pump air in to see if it is sealed. Look for air coming out around the prop shaft.
If it still leaks, replace all seals in the lower end.