I have an older montgomery wards mower and the starter makes a loud squealing noise and does not turn the flywheel.I have sprayed 10w40 around the starter and also tried filing the plastic gear thinking it might be a problem as it showed some wear.This just started occurring and I was wondering is the starter need reapired or replaced or is there something I can do to get it to work correctly.I also noticed that when I lift the top piece of starter the teeth do not reach the flywheel and create a bond as I might expect them to.The oval piece that I see below the spring just spins as well as the top.

Well, the engine can be turned manually can't it?

Yes I can turn the flywheel by hand.The plastic gear does not engage flywheel and the teeth on the gear seem to be about 1/8" below flywheel.It seems as if it don't pop up high enough and the starter just makes sqealing noise.

Remove the starter, carry it to your local small engine shop, and let them test it for you there.