Alexander the Great conquered a massive empire that stretched from the Balkans to modern-day Pakistan. But if the Macedonian king had turned his attention westward, it’s possible he would have conquered Rome, too, feasibly smiting the Roman Empire before it had a chance to arise.

So why didn’t Alexander the Great try to conquer Italy? The answer may be that he died before he got the chance. The king of Macedonia ruled from 336 B.C. to 323 B.C., when he died of an unknown illness in Babylon at age 32. Alexander’s empire fell apart shortly after his death. Had he not died, however, it’s possible that Alexander would have targeted Rome and, with his substantial forces, defeated the Eternal City.

Some ancient texts suggest that Alexander the Great was planning a military campaign in the West that involved conquering parts of Italy, among other locations along the Mediterranean. The Roman historian Quintus Curtius Rufus, who lived in the first century A.D., claimed that Alexander the Great had planned a series of conquests that, if successful, would have expanded his empire all the way to what is now the Strait of Gibraltar. Alexander planned to build 700 ships to support this invasion, Rufus noted. Other ancient writers made similar claims.

“The Romans were convinced that Alexander would have attempted the conquest of Rome, but for modern historians, it is impossible to say,” Nikolaus Overtoom, an associate professor of history at Washington State University, told Live Science in an email.

Some ancient writers claimed that after Alexander died, his secretary, Eumenes, gave one of Alexander’s senior generals, Perdiccas, plans that included the conquest of part of Italy, Robin Waterfield, an independent scholar with a background in classics, told Live Science in an email. “Now, some scholars believe that the [plans] are not genuine — perhaps a forgery by Eumenes, or perhaps the whole story arose years, even decades later,” Waterfield said. However, “I think the balance of evidence is that they’re genuine.”