Cragar SS lug nut trouble

They take the shanked lugs. You have the wrong lugs. I have some new lugs from an old project I sold. I can measure them . Your lug looks different. They should be 7/16 20 with a 11/16 head. It definitely takes a shank style lug.

I had the conical Cragar wheels . They had a tapered face on the wheel. I had "Conica"The "Shanked", and "Conical shank" lugs . Went through the same thing with summit.
.592 shank...