Odd fight in that Holyfield had seen better days. I’d pick Dempsey certainly, & I might stay with Dempsey even against a Holyfield five years earlier, though that would be an titanic scrap. Dempsey was mentally in 1919 everything Tyson wasn’t - namely, hungry & disturbingly determined. He won’t be rattled by Holyfield’s bullying tactics, & will actually throw in combination unlike late 90’s Tyson. I pick Dempsey - not an easy fight but a prime Holyfield would have a significantly better shot.