Hi Brenden,
Sometimes thread or other gunk gets trapped under the bushing. There's a great tutorial on how to remove it at the Singer Featherweight Shop. They make a special tool to help pull the bushing, because one thing you really don't want is damage to the outer surface of the bushing, along which the handwheel spins when disengaged from the drive.
Is there a screw in the bushing, or a taper pin? I removed a taper pin once -- real pain unfortunately!
https://singer-featherweight.com/blo...collar-bushing
Matt