Jack Dempsey and Harry Wills are my number 9 and 10 on my all-time hw list. Dempsey is over Wills mainly due to him having the real hw title - and me thinking he would beat Wills. But imo Wills beat the better fighter when he defended his black hw title. So, for me the question arises if the black hw belt might have been more worth at their time due to Wills defending it against the better fighters in comparison to Dempsey´s defenses.
I'm not really qualified to answer this question because I've never really put a lot of stock in titles - a champion always bares further investiagation, but that is all. I don't give a **** what bauble he has if he didn't fight the best. Wills should be ranked above Dempsey on every HW list in my view, and putting stock in titles is the only way to allow the reverse.