In 63, Catilina got back on his feet. Last year had been a disappointment; this year, however, he was determined to run again. And this time he would not be deserted by his supporters as he had been by Antonius. He would have a solid following.
Much has been made of the infamous dinner part which Catilina held "sub rosa," below the rose- - meaning, in absolute secret. One historian says that he sacrificed "a lad" and did some sort of divination with his entrails, afterwards eating them. Sallust talks of bowls of human blood mixed with wine being downed in toast to an unholy oath. With such unfairness is Catilina judged that, when reading lurid accounts of his dastardly deeds, his own words come as a breath of fresh air, such as the speech he gave then. He addresses his partisans warmly as friends, praising their courage and loyalty. As always with Catilina, he words are equal parts charm, idealism, and cynicism. At the same time as he calls on the sacred bond of friendship, he belittles it as being nothing more than an "similarity of likes and dislikes." He rants against the rich oligarchy that spends gold on luxury while the common people cannot even put a roof of their heads. He finishes with a flourish:
"Awake, then! Here, here before your eyes, is the liberty you have often yearned for. . . Use me as your commanderor as a soldier in the ranks: my heart and hands shall be at your service. These are the objects I hope to help you achieve when I am consul- - unless I indeed deceive myself and you are content to be slaves instead of masters." (Sallust)
At no point in the speech, note, does he mention armed insurrection: except in the pretty line about commanders and soldiers, which could be metaphor as much as anything else.

He was born in 108 B.C. His family, while old, had not produced a consul for a quite significant amount of time. He served in the military under Publius Servilius Vatia around 70 B.C. His role in the clash between Sulla and Marius is debated: some say he had family ties by marriage with Marius, others maintain that he was a complete Sullan. According to those historians who side with Cicero, he helped to murder Marcus Marius Gratidianus, and is described vividly as having run through the streets carrying his severed head ("still breathing"). I personally prefer to think of this as black propaganda. Add to this the fact that he seems to have been married to Gratidia, the man's sister, and the story becomes still more unbelievable.
In 73 B.C., he was taken to court for corrupting the Vestal Fabia. If he did we do not know. If so, then we must believe he was a man almost incredibly reckless with his life, as well as with those of others. The punishment for a man who defiled a Vestal was to be whipped to death. The girl's fate, however, was to be buried alive.
Catilina was acquitted, partly due to the testimony of Quintus Catulus, a staunch conservative. Marcus Cato also testified. Cato was, of course, the last man to speak on behalf of anyone he did not believe to be entirely innocent, he was famous for his integrity and uncompromising morals.
Catilina was taken to court several more times throughout his career, for murder and extortion. This certainly did it's part to damage his reputation, but let us not forget that each time he was acquitted.
What was he like? Well, it is safe to assume he was charming and handsome, judging by how he got around. He was also certainly bisexual. Cicero tells us about the young men who frequented his society. "He. . . became the lover of a number of them. . . he even disgustingly allowed others to make love to himself." Cicero also mentions a certain Tongilius, probably as freedman, as the long-time lover of Catilina. Catilina supposedly had legendary physical strength. He was also mentally fit. Sallust writes that "his mind was daring, crafty, and versatile," calls him "a man of flaming passions" and adds that "his monstrous ambition hankered continually after things extravegant, impossible, beyond his reach."
It seems that at some point during this time, Catilina suffered some great personal tragedies. His wife Gratidia died, as did his grown-up son. He was accused of murdering both of them. For the sake of expediency he seems to have remarried quickly, to a certain Aurelia Orestilla, whose mother he had known intimately and who he was rumored to have fathered. Such complex intrigues were not unique to Catilina alone. Gaius Julius Caesar himself seems to have carried on affairs with a glamorous lady named Servilia and with her daughter, Junia Tertia, as well. Servilia's son, Junia's brother, was Marcus Junius Brutus, who lead his assassination.
In 66 he would have stood for consul, but was prevented by that troublesome charge of extortion, of which he was eventually acquitted. Feeling fed up, we are told that he organized a conspiracy of grand proportions. He and some other depraved and put-upon friends had intended to assassinate the new consuls. Their designs were discovered, and, according to Sallust, they calmly rescheduled the party for a later date, with most of the senate on the guest list this time. Alas, this plan as well failed, because Catilina forgot to give the signal.
Very well and good, but I would very much like to be able to ask Sallust, Cicero et cetera some questions. First, if Catilina's intentions were discovered, why was he allowed to remain at large? Secondly, Cicero informs us that Catilina was exceptionally clever, daring and thorough in all his plans. Sallust calls him cunning and capable of any intrigue. If this is so, how could he have been so scatter-brained as to have forgotten the crucial signal? The story rings false on several counts. And if it is true, how could such a bumbler be any danger
to the state?
In 64 he ran against Cicero and, at first, in collaboration with Gaius Antonius Hybrida, a nonentity but apparently an old friend of his. Cicero delivered a damning speech against both of them, In Toga Candida, at one point. In it, Antonius was charged with crimes no less heinous than Catilina's-- yet this didn't prevent Cicero from eventually allying himself with him in order to knock Catilina out of the race. He even stooped to bribery; promising Antonius that if he cooperated with him, he could have the province Cicero would be offered to govern after his consulship.
Catilina lost. This isn't, remember, necessarily a reflection of popular vote. When election time came around, the Roman people were divided into "centuries" according to their means. The patricians were divided into several centuries, even though there were fewer of them; while those on the lower rungs of society, obviously the majority, were grouped into a few large centuries. Each century got one vote.

"I do not intend... to make any formal defense of my new policy. I will however explain my point of view. What I am going to say implicates no consciousness of guilt, and upon my honor you can accept it as the truth. I was provoked by wrongs and insults, and robbed of the fruits of my painstaking industry, and I found myself unable to maintain a position of dignity. So I openly undertook the championship of the oppressed, as I had often done before... I saw unworthy men promoted to honorable positions [and] felt myself treated as an outcast on account of unjust suspicions. That is why I have adopted a course of action, amply justified in my present circumstances, which offers a hope of saving what is left of my honor. I intended to write a greater length, but news has come that they are preparing to use force against me. So for the present I commend Orestilla to you and entrust her to your protection. Shield her from wrong, I beg you in the name of your own children. Farewell."
If we are to believe Sallust, this is one man's final plea for understanding from a world that had already hardened its heart to him: a letter left by Lucius Sergius Catilina at the house of senator Catulus on the eve of his flight from Rome. Though Catilina speaks of force, what had in truth driven him from his city was words, the fiery allegations of the accomplished rhetorician Cicero, a man with incredible influence throughout history. The founding fathers studied his writings, and he was a role model for leading personalities in the french revolution.
Most if not all of what we know of Catilina comes from those speeches, so it shouldn't be a surprise that the image we are left of his is of a dangerous, possibly insane insurrectionary. In painting the portrait of Catilina, I intend to be as non-judmental as possible.
What do we know of Catilina? He was of the old but impoverished Sergius family. He posed as a radical politician, though this is debatable. When he speaks of taking up the "championship of the oppressed" he is referring to the main plank of his platform: complete cancellation of debts. This idea appealed to the poor, frightened the rich out of their wits, and was welcomed by young scions of the patrician classes who had squandered their money, as young men who take their wealth for granted are wont to do.
Catilina had been accused and acquitted of an astonishing array of crimes: murder, extortion, and corrupting a Vestal Virgin. He benifitted from the horrific proscriptions of Sulla. The court of slander charged him with many, many more: including marrying his daughter, killing his own son, and doing away with his brother in law. He had quite a reputation. Cicero informs us that "No one has ever had such a talent for seducing young men," and that he had "raped children in their smocks practically at their parent's knees."
Catilina's basis of support was mostly among the young. Cicero and others would like us to believe that every one of his followers was a hardened criminal, but this hardly seems likely at their age. Behind the scenes it is probable that he had the support of Julius Caesar and Marcus Crassus, at least for a little while.
Catilina was known for his physical strength and endurance. Apparently he had great military talent. He also had legendary charm and charisma. He was intelligent, politically passionate, but also, I think, politically naive. Against an astute politician like Cicero he stood little chance. Cicero understood this, and I believe this was partly the reason why he picked Catilina for his scapegoat.
Prior to the alleged "conspiracy," what was Cicero's relationship to Catilina? Well, the Vestal Catilina was accused of having sex with was the half-sister of Cicero's wife, Terentia. When Catilina was accused of extortion in 66 BC, Cicero had considered defending him. "We have the jury we want," he ironically wrote to his friend Atticus. He appears to have dropped the idea, and Catilina was got off anyway. When they were running against each other for consul in 64, he considered forging an alliance with Catilina against the third candidate, Gaius Antonius. This idea he also dropped in favor of working with Antonius, and it was Catilina who was left behind.
During the course of the "conspiracy," Cicero charged Catilina with crimes so diverse as to make one dizzy. Supposedly he planned to murder every one of the senators, burn Rome to the ground and enslave everyone. It isn't clear, of course, why Catilina would level the town which he desired for his domain. Evidence of the conspiracy is limited to some letters that could easily have been forged by Cicero, a stockpile of ornamental swords found at the house of Cethegus, one of the alledged conspirators, and confessions from some of Catilina's friends, possible extracted by threats and intimidaton. So it's possible though not probable, that Catilina might have been altogether innocent of wrong.
While Catilina lived, Cicero blackened his name with all manner of insults, accusations and slurs. But after his death, at the trial of his friend, Caelius, a former supporter of Catilina, he sang a different tune:
"Catilina had many excellent qualities... he undeniable possessed a gift for stimulating his associates into vigorous activity. Catilina was at one and the same time a furnace of inordinate sensual passions and a serious student of military affairs. I do not believe the world had ever seen such a portent of divergent, contrary, contradictory tastes and appetites."