I have the same model machine with the same problem!
The shaft of the bobbin winder 'froze' (apparently from old or incorrect lubrication). When it froze, it's rubber wheel (which they call a 'ring'') that is driven off the back of the main hand wheel (to the left of the winder) developed a flat spot, so it also had to be replaced. (Enter the machine model number at /www.searspartsdirect.com to see how it fits together. Their exploded parts diagrams are excellent.)
Two screws hold the top cover on the machine, and two screws hold the bobbin winder to the underside of the cover. Note that the winder assembly mounts are slotted, so when reassembling, the winder must be adjusted to engage with the drive wheel. (Note its old position.)
You might be able to use a penetrating oil to clean the bearing without dis-assembly of that shaft from the bearing, but that didn't work for me.
I tried to get a whole new bobbin winder (Sears pt # 214458), as well as a new ring (Sears pt # 61662). but Sears no longer stocks that.
I found the ring cheapest at http://www.a1sewingmachine.com, but they no longer had the winder.
I found both parts at http://sewingmachine221sale.bizland.com/store/page21.html, but before the order arrived, I was able to repair the old one, so if the winder does arrive I'll have it as a spare.
I made a fixture to remove the press-fit wheel (that mounts the ring) from the shaft, so I could clean and re-lube the shaft bearing. I used a lathe to drill a 8mm hole > 40 mm into the end of a 1/2 in. aluminum rod, and mounted the rod in a press, and used a 3/16 steel pin to push the shaft out of the wheel. Clamping the rod in a vise and using a pin punch /hammer might also work, but it was very hard to separate them, so that might not work.
When lubricating the shaft/bearing of the winder, be sure to use a good quality sewing machine oil. I've had bad experiences with bearings like this lubed with generic oil (like 3-in-one oils) which gummed things up in a very short time.
Paul Higgins[email protected]