Strange fight I believe. I don't think the styles would mesh at all for an entertaining fight. At the time of the Hopkins/Trinidad fight, Bernard still had some gas in the tank, but at middleweight could he sustain enough pressure to give Leonard problems? He wasn't the same Hopkins that tracked and took apart Glencoffe Johnson at this stage. Hopkins very much preferred opponents to come at him later in his career, Leonard wouldn't do that...I think Leonard would give the better "impression" of winning with movement and flurries, and sell it enough to take a decision.
Probably the tail end of Hopkin's prime, but just the year before he showed against Echols that he still could exhibit real quality aggression and tenacity. I don't think the past prime, blown up Leonard of 1987 would be able to handle that kind of pressure and physicality. Either a clear decision or a late stoppage for B-hop.