This is two-part question.
What are the chances Wlad retires without being beaten again, or even unchallenged? 100%? 80%? 50%?
If you think he gets beaten or challenged (competitive fight... maybe even a knockdown of Wlad).... by whom?
I already know one answer. That'll be Ross.... saying 100%.... and it'll be Fury.
But what about the rest?
Personally, I'm pessimistic. Way too many timid sheep have paraded in front of Wlad, helping him fatten his record on his way to the boxing HOF. Lots of big mouths.... only to turn in a pretty subpar job come fight night. Now there's these big, young, fast, knockout artists (Anthony Joshua, Joseph Parker) coming up........ but it's a dollar short and a day late. Maybe post-Wlad we'll have some classic battles between the Furys, the Wilders, the Joshuas, the Parkers, etc. But for this 2-3 year window where Wlad will still be around..... the pickings are slim. You look at the currently ranked HWs and it's a "who's who" of fighters Wlad has already beaten (Jennings, Povetkin, Thompson (twice)).... fighters who have no chance against Wlad (Stiverne, Arreola, Molina).... or fighters who will be peaking when Wlad has already retired.
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