The woodruff key is still in there but the front part of it is broken off. The pictures tell me the pulley got loose, wobbled, and broke the key. The wobbling pulley and broken key have eaten a groove in the crankshaft and timing gear.
To properly repair that you will need to remove the crankshaft and have a machine shop weld up and regrind the nose of the crank and the keyway, then replace the timing gear and pulley.
Yes, that time belt is done for - quite a long time ago.