Not even close. Willard is a cave man coming out from his cave and blinking in the sunlight as he watches Wlad pilot a jet fighter across the sky.
Dempsey has like 3 rounds to really explode and try to take Wlad out of there, but after that he’s cooked. It’s very risky to try and contain Dempsey on the inside like Wlad loved to do so it wouldn’t surprise me much if Jack got it done early either.
Wlad would destroy Dempsey. Too big, too skilled, controlled distance too well and punched harder than Jack.