Any chance you checked for leaks before to took the tire off ? Like soapy water, and look for bubbles ? If it's leaking thru the side wall, try the soap film on the inside. Or could it be leaking from the bead thru the screws that you have in the wheel to keep the low pressure tire from spinning. I have seen this before, and what fixed it was putting silicon seal in the screw holes, and indents in the tire bead. Sometimes the screw goes too deep into the bead, too long screw, and or narrower bead.
Or of course, install an inner tube, I think Hoosier has big slick tubes. One possible plus would be the tire will build more heat with the tube , because of friction between the tire and tube. Maybe shorter burn-outs then ?
Let us know what works.
Jon