The best worst Roman ever would have to be Brutus. This guy couldn’t make up his mind whether he was coming or going. On the one hand he killed his best bud, Caesar. On the other, he only did it to prevent him from becoming an evil megalomaniac. Right idea, wrong intervention. It happens. Although eventually you run out of friends.
Brutus’s biggest problem was that his plans weren’t very well thought out. After the assassination, he had this whole speech to give to the Senate about how this would be the beginning of a return to a republic. Unfortunately, the Senators took one look at the bloody knife and ran away screaming like little girls. While Brutus was chasing after them shouting out the bits he’d spent too long the night before memorizing, Mark Antony got word to Caesar’s wife and gathered up Caesar’s money and papers.
Stealing another march on Brutus, Antony called a senate meeting for the 17th, and made sure he was in charge of the agenda. Now the way Antony could see it, he had two choices. He could outlaw Brutus and Cassius as the ringleaders of the assassination and honor Caesar as a hero, or he could declare Caesar a tyrant and honor Brutus. (He briefly considered a third choice, declaring himself emperor in Caesar’s place, but he didn’t want Brutus getting any more ideas.)
Now seeing as how Caesar had designated all the public offices for the next five years just before he died, no one in power was too keen to have his decisions rejected. (You can see where this is going, can’t you?) So Antony stayed up all night writing, and the next morning delivered a speech to the populace where he displayed Caesar’s bloody wounds with outrage. It was a very good speech, but all anyone ever remembers is something about “friends, Romans, and ears.” He also mentioned that Caesar left money to every citizen in Rome in his will. (Never underestimate the power of cold, hard cash.) Needless to say, Brutus and Cassius were driven out of town quite quickly.
Meanwhile, Caesar’s main heir, Octavian heard about his uncle’s death, but with great family feeling and devotion, decided to hide out in Italy until he learned which way the wind was blowing. Pretty soon he realized the wind was blowing pure Antony, so he climbed out from under his rock and moved towards Rome where he received a hero’s welcome. Antony, however, was less welcoming, even going so far as to refuse to give him the money Caesar left him in his will. Antony didn’t like to share the limelight (or the cash). Fortunately, Octavian had some rich friends who were eager to lend him some gold (they didn’t like Antony either).
By this time, Brutus and Cassius had stopped fleeing, and had rounded up an army of supporters. Brutus went to Athens to study (so he could make better plans) and gain support. By the time he was ready to leave he controlled all of Macedonia (and he didn’t even have the help of Machiavelli!). Cassius went to Syria, and between the two of them they controlled the eastern, richer part of the Roman Empire.
This did not sit well with Octavian and Antony. In fact they decided to put aside their differences and declare war on Brutus. With great effort, they almost managed.