I think Alexander would have won. Remember, the Romans of the time were still only a Regional power. They only had the middle section of Italy under their sway. All the Greek and Samnite cities south of Latium/Campania were still independent. The Gauls were still a huge threat to the Romans in the Po River valley (northern Italy) as well. This was also pre-Marian reforms - even pre-Punic Wars era Romans. I think Alexander would have adjusted his tactics accordingly. I think he would have taken Carthage, then moved on Scicily, then secured the Greek cities in Magnae Graecia (south Italy), then taken the rest of Italy, burning Rome to the ground, Thebes-style. Despite the movies, I don't think he would have moved on Gaul. At this point he probably would have made an expedition to the Pillars of Herakles to place his foot in the opposite side of the World Ocean from India. Subsequent Emperors, Alexander IV and V would have conquered Gaul and Dacia, securing the empire's northern borders. Contacts would have been made with China. Alexander VI completes the conquest of India. teehee