Could Alexander have conquered Italy?, page 1

Perhaps.

Rome was a real mess. About 40 years before his birth, the Gauls sacked Rome and Rome began a series of wars as she tried to expand. Along their European frontier, there was a series of revolts that kept the army running. Rome also expands south to the rest of Italy... but nobody's terribly happy to see them coming. If he'd timed his attack during the Second Sammite war, then he would have caught Rome with her forces somewhat overextended... he could have bargained with the Etruscans in 311 BC. With those three fources and the Hernici revolting, Rome would have eventually fallen.
www.unrv.com...

HOWEVER... Rome had been using Greek military tactics (the phalanx) and abandoned them after the sack of Rome by the Gauls. They added new types of armament (triarii, rorarii, accensii, hsati, and principes -- each with different experience and different types of weapons and armor.) This added flexibility to their abilities.
en.wikipedia.org...

Alexander was quite heavily "into" the phalanx, though he also used the "flying wedge" en.wikipedia.org...

His overall strategy was to use his flexible phalanxes to force the enemy to try and adapt to new types of attack and to force them onto ground that was not easy to fight from. Rome may have gotten some of the same tactics from the Samnites.

I think it would depend on who he came up against. There are no notable military leaders (that I can find) from that era, so it's hard to directly compare tactics with tactics. But Alexander was a solid strategist and the Romans tended to get a bit cocky. I'd give odds to Alexander, but not overwhelming odds.

reply to post by Byrd

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The Gauls were tough,They invaded Greece and sacked Athens.

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