It gets stuck because the pin / bushing is clogged. It will continue to get stuck until you clear out the built up gunk. You can try solvent and wiggling the pin, driving it back and forth. There is also a grease gun like device that injects high pressure solvent to break up the clog.quote]
I have one of those zerk rejuvinator maintenance tools. Works quite well. I got it either from Northern Tools or HF. You just load up the cylinder with light oil, attach it to the zerk just like a grease gun, then hit the head with a mallet. It shoots the light oil into the zerk under high pressure and most of the time clears the clog. You can then just grease normally. The few times it hasn't worked I've pulled the zerk and found impacted dirt inside the fitting. (from poorly protected zerks at the bottom of a 4n1 bucket).