Fitzsimmons would come through on top after a dangerous shootout. Walcott had the ability to get close and start denting Fitzsimmons' armour, but he's dealing with a multi-layered counter-puncher who would more than likely shirt-circuit the smaller battler after some exciting clashes. For Walcott to have to reach and jump in to plant Fitzsimmons he would be leaving himself open to too deadly a puncher to be victorious.
Walcott did in fact challenge Bob Fitzsimmons to a bout along with most of the top heavyweights of the era. The proposed fight would have pitted a faded Fitzsimmons against a prime Walcott, which might have resulted in a win for Walcott. Prime for prime I would favour Fitzsimmons because he was bigger and slaughtered pressure fighters.
For sure. Walcott put out a lot of challenges that could have resulted in tremendous fights. Tommy Ryan, Young Griffo, Tom Sharkey, Marvin Hart, even Jim Jeffries. "Since no welterweight or middleweight will fight me I am compelled to go to the next class. Will any heavyweights fight me?" Joe Walcott Police Gazette Oct 13, 1900.
I guess Ryan would have been the pick of them. Harder to take when they never came off. Burley-Robinson for example.
If this fight had taken place it would have been the two best welterweights (up to that point, perhaps even pre Robinson) fighting for the middleweight title. I could make a case that this is the greatest fight that could have been but never was.
I would keep the pound in my back pocket because anything could happen. If I had to bet it then I would go with Walcott to pressure the slick Ryan and force the fight enough to win. Of course Ryan doid have sucess against some short pressure fighters like Tommy West. Joe Walcott two division champion. I think.