"You want compromise? How's this? 20 years in the can. I wanted manigot, I compromised, I ate grilled cheese off the radiator instead. I wanted to fuck a woman, but I compromised, I jacked off in the tissue." - Phil Leotardo
According to Slavoj Žižek "An normal paternal authority is an ordinary man who wears phallus as an insignia, he has something which provides his symbolic authority." For Tony Soprano, the cigar is his phallus, the symbol of his paternal authority in the domestic family as well as in the hierarchical structure of the crime family. When we first meet Tony in the opening credits, he is seen driving from New York to New Jersey and lighting up an enormous cigar along the way, obviously he is not a cigar, he possesses the cigar. This means he is not what this phallic insignia represents, but he possesses this phallus because of the role he is attempting to play and the authority derived from the phallic insignia. In the Mafia mythology of crime dramas, cigars are common place, cigars are synonymous with gangsterism and symbolic of excess, power and wealth. Notably in the opening credits, he only lights up the cigar after officially entering the Garden State through the New Jersey Turnpike; indicating that his authority is in New Jersey and not New York.
In one of the most overt use of this phallic symbol in the pilot episode, Tony has an anxiety attack whilst tending to a barbecue and puffing on a large cigar his ducks fly away. At first he appears content in his role preparing meat, a role once played by his father, for his loved ones whilst his beloved ducks remain in his pool. But when the ducks fly away, he suffers the attack and the cigar drops from his mouth, he is castrated. Tony's paternal authority is dependent on the presence of the family unit, whether that be a traditional nuclear family or a criminal organisation, consisting of subordinate members. The fear and anxiety of losing his loved ones, as well as his criminal brothers, would be a castrating experience for Tony - in the sense that Tony's position at the head of the table would be rendered meaningless. Yes, his position is one of power, but he dependent on the underlings for income and this generalises to his domestic life - there he is dependent on his family for love, comfort, food and other forms of gratification.
Many characters in The Sopranos suffer from or die from cancerous tumours or legions, this could be indicative of the nature of organised crime. The fact that smoking often is the cause of cancer may imply the doomed fate of those who play "Godfather". Johnny Sack spends most of his time on camera smoking and later dies of cancer. Though Sack is never seen smoking a large cigar, just cigarettes which are smaller and slimmer. This may imply a lack of potency in Sack's character or reflects his pragmatic approach to business. Something which Tony, and other characters, lack as they use violence to achieve many different aims. Interestingly, Gary Cooper, Tony's ideal American, died of prostate cancer. This is the true price of Tony Soprano's authoritarianism. Growth for the sake of growth, is this not the ideology of the cancer cell.
In the final episodes, Phil Leotardo becomes the Boss of the Lupertazzi crime family, one of New York's legendary Five Families, Leotardo is visibly smug and finally content in a position of power. It is only in this position of authority, as the paternal figure of a large crime family, does Phil light up a cigar. Prior to achieving such status in the underworld, Phil spent 20 years incarcerated and it is constantly suggested that during his incarceration that he engaged in homosexual intercourse. In years since his release from prison, Phil was notably aggressive and arrogant in his conduct. He patronised Tony during a sit-down and actively provoked retaliation from Soprano's soldiers in the aftermath of his brother's murder. Leotardo later orchestrated the murder of Vito Spatafore, out of deep feelings of violent homophobia which most likely stem from the self-hatred derived from his own activities in prison. It appears as though Phil Leotardo suffered from a massive Napoleon complex that could even rival Tony Soprano's "mother issues" and anxiety attacks.
However, it seems that Phil Leotardo may fall into the category of ridiculously obscene paternal antagonists, like Frank Booth or Bobby Peru, that Žižek identified in several David Lynch films. Phil overcompensates for his own feelings of sexual deviancy and emasculation through "uber-macho" behaviour. Particularly, in the form of over-the-top displays of violent homophobia, obscene threatening behaviour and horrific acts of violence. It could also be that Phil Leotardo, like Frank Booth and Bobby Peru, does not just possess a phallic symbol of authority like Soprano. But that he actually is the phallus. In the words of Žižek "It's not simply that they possess phallus, that they have phallus as an insignia of their authority. In a way they immediately are phallus."
In the finale, Phil Leotardo is shot in the head and chest before being run-over by his own car, which actually squashes his skull for all to see, this is symbolic of the destruction of the phallus and the paternal authority it represented. This fitting end is similar to the one met by Bobby Peru in Wild at Heart. Peru died by falling onto his own shotgun and literally blasting his head off by accident. The bloodied stocking Bobby wore to conceal his identity, containing the remnants of Peru's head land nearby, resemble a used condom. Just like Bobby Peru and Frank Booth, Phil Leotardo was an obscene paternal presence, devoid of any anxiety, fearless in the face of the consequences of his exuberant machismo - as exemplified by his violent tendencies towards torture, mutilation, beating and rape as well as murder.