Welcome to TF, Leodora!
As Capt.Bill11 implies in post #2: - Clear picts help greatly with diagnosis.
We have 1977 34' Tollycraft... same circa boat that may have similar rudder shaft glands with fasteners and tighteners. That said; your description does not seem the same as ours - again, send good pictures.
On ours is a large [1.75" or so] tightening nut on top of threaded rudder shaft encasement. If yours is similar, tightening that nut may cinch the packing gland tight enough to stop, or greatly slow the leak.
Three things before starting to apply pressure to any portion:
1. Spray the big nut and its threads as well as all other rudder fasteners in that area liberally with good penetrating oil each day for at least a few to several days before trying to wrench on things. Good idea to lightly
tap on the big nut and other fasteners after each spraying… helps to loosen corrosion and create paths for penetrating oil to migrate into.
2. Be ready with all potentially necessary tools as well as to have bilge pumps (easy access to emergency pump also if it becomes necessary) in good order if per chance the metal or other material at rudder is in really bad condition and for some reason fails substantially while working on it with boat still in water… ALSO – have a plan ready
for quick haul if needed.
3. For maximum safety have boat on the hard while working on its rudders… then you can really get into rudder repair and make sure everything is correct for lasting in good repair for many years.
Good luck – Looking forward to seeing photos of your rudder stem in boat bilge by transom.
Happy Boating Daze! – Art