I tend to look at this one a little differently. If we are talking accomplishments and historical impact, then I say Ray is an easy winner. If we are talking a mythical match up where size is made equal and all other attributes adapt accordingly, I feel this is a 50/50 fight.

Ray had better fundamentals and was VERY close to Roy in terms of athletic ability, but I feel Roy's slight edge in athleticism combined with his unorthodox/creative style would have presented significant problems to Leonard. I think Ray was very good at adjusting during fights and he was able to vary his weapons/strategy once he figured out the other guy's weaknesses. Roy was so damn unorthodox and unpredictable in his prime that I see Ray requiring numerous rounds to start to feel comfortable and spot the openings. This would be a fantastic fight.