Okay, you seem to have enough washers.
The gasket should be compressed against the inside wall of the cooler to get a seal. Sometimes, even though it is compressed and doesn't leak, the whole valve/bulkhead fitting assembly will rotate a bit when you twist on the valve, and that's okay -- as long as it doesn't leak.
Is the fender washer on the inside larger than the gasket? If so, due to the curvature of the cooler, that could prevent the gasket from being compressed properly. Typically I think I have seen these with just a gasket and lock nut on the inside, but a washer could be okay.
When you try to tighten it up, what prevents it from tightening?