It's an interesting comparison, IMO, & I ultimately consider their placings in history more or less interchangeable with one another. Dempsey fought & beat the better opposition on the way up, pre-title --- Holmes beat better rivals after they'd lost their title, coming back for a long run after Dempsey had chosen to stay retired. Dempsey defeated better men while holding the crown --- Holmes, many more fighters, however.
Similarly, I could see a case for either man besting the other head-to-head. They are both somewhere between the top-5 & 10 of all-time.
Similarly, I could see a case for either man besting the other head-to-head. They are both somewhere between the top-5 & 10 of all-time.
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