Pressing the brake pedal makes the pistons in the wheel cylinders move. If one or more moves too far, it can either come all the way out of the wheel cylinder, or get stuck on build-up or rust in the wheel cylinder bore. IF the brake shoes move out far enough the can 'fall' off of their guides on the backing plate and not retract like they should.
Try lifting the shoes away from the backing plate and see if they will retract like they should. You may need to press them together to compress the wheel cylinder pistons. IF one piston won't move, then you either need to pull the boot off to see what is keeping it from retracting or open the bleed plug and try again.
If it isn't out all the way, then it may be jammed on crud. Careful, light tapping on it with the bleed plug open should get it to go back in. Take care to not let it get cocked in the bore.
If the piston has come out all the way, then clean the inside of the bore, reinsert the spring (if there is one), rubber, and metal piston in the bore, put the pushrod and rubber seal back on the cylinder, put everything back together and bleed the brakes.
Sounds like the brakes just aren't setting back into place. Look at the the pins coming out of the wheel cylinders and make sure they are set into the shoe fully. Gently tap both shoes together with your hands and retry the drum.
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