I don't think digging to Dempsey's body will work because it will leave you open on top. Despite Kabayel having 50 lbs on Dempsey, i think Dempsey is too quick and gets Kabayel out of there in six. A bigger slower opponent (not that Kabayel is slow but slowish compared to Dempsey) is tailor made for Dempsey. Dempsey tko 6.
A great guide to fantasy fights would be for one fighter who's challenging a legend is to have actually accomplished something . Kabayel hasn't done anything as of 7/27/2025 to warrant a Dempsey fight matchup, much less a convoluted notion he'd win