What Greek military hero do you admire most?

[M. Caecilius]

So which Greek leader gave Rome the most trouble?

Achilles and Odysseus, if you believe the Roman claim of being descended from the Trojans. :grin: Seriously, though:

Clearly Pyrrhus who was a great tactician, albeit a bit naive as a strategist.

I agree.

Another Greek who caused the Romans some problems was Philip V. Not during the Macedonian War, but during the Hannibalic War. His juncture with and support of Hannibal could have struck the death blow to Rome. Fortunately for them, the Romans could turn the Aetolian League loose on Philip V, but there was enough heartfelt hatred left to start a war within two years after the very costly Second Punic War.

Other than those, Cleopatra and Mithridates, it seems the Greeks were rather tame when compared to the revolts you get on the Iberic peninsula, in Gaul, in Mauretania, in Judaea, to the foreign enemies in Parthia-Persia, and to the ultimately greatest threat the Romans posed to each other.

The struggles between individual cities or groups within cities (stasis) seems to have caused a lot of headaches to the governor (and Emperor) though.