The Sopranos: Phil Leotardo - The Last Real Mobster

Let me tell you a couple of three things. Forget that Phil Leotardo is a closet homosexual. Forget that he’s a walking meme. Forget the fact that he has the power to transform himself into a house.

Phil Leotardo is one of the most recognizable characters from The Sopranos. Played by the legendary Frank Vincent, he has some of the most memorable and funny quotes in the entire show. But Phil is much more than just a meme. He’s not only the final antagonist of the series, he also represents the end of the old school days of the mafia, both in a literal sense and in a metatextual one.

So in this video, let's examine Phil Leotardo, the last real mobster on the show.

Phil Leotardo is a captain in the Lupertazzi crime family of New York. He’s introduced at the beginning of the fifth season after having served a very long prison sentence, though we’re never given an exact answer as to how long he was in prison.

After he gets out, he serves as one of Johnny Sack’s key enforcers in the war between him and Little Carmine. After killing Carmine’s supporter Angelo Garepe, his close friend Tony Blundetto seeks revenge and ambushes him. Phil survives, but his younger brother Billy is killed in the attack.

Phil is enraged by this, and demands the opportunity to avenge his family. Tony Soprano ends up killing his own cousin to prevent Phil from torturing him, which robs him of the opportunity for revenge. Though the beef is eventually squashed, resentment continues to linger in Phil.

After Johnny Sack ends up dying in prison, Phil takes over as boss of the Lupertazzi family. Seeing the New Jersey family as beneath them, he refuses to negotiate as equals and instead takes a hard line. This leads to conflict between the two families which eventually turns into all out war. Though Phil manages to take out many of Tony’s key guys like Silvio and Bobby, Tony is able to turn Phil’s men against him before eventually taking him out. Phil’s dreams of being bossed end up crushed like a watermelon under a car tire.

Alright real quick before we get into the analysis of Phil’s character, we have to get something out of the way. Phil is gay. Or at least subconsciously he’s in the closet. I’ve avoided making a video on this topic because it’s just so obvious and plenty of other people have done it. But I would be remiss if I didn’t mention it here.

In the sixth season it’s revealed that Vito Spatafore is gay. Phil is outraged by this, seemingly because Vito is married to his cousin and he views this as a disrespect against his family. He becomes absolutely obsessed with killing Vito, focusing on it even more than his actual business. However it becomes clear that his deep fixation on killing Vito goes beyond the typical mafia homophobia, and that is actually self-hatred over his own conscious or unconscious desires.

There are a ton of hints that Phil is gay. When he and his guys attack Vito in the hotel room, he literally emerges from the closet. When they beat Vito to death, he grabs the sheets almost as if he’s getting a sexual thrill from the encounter. Also after they kill him, they shove a pool cue up his ass, which while you may say is an attempt to humiliate Vito, still has really obvious sexual overtones.

“I know Vito’s bottom was impacted, if that’s what you’re referring to.”

- Phil Leotardo

It’s commonly believed among fans that Phil Leotardo had gay sex while he was in prison all those years, and that he was projecting that shame onto Vito. When he talks about all the compromises he made in prison, he specifically brings up sex. Now he says he jerked off in a tissue, but we all know that another compromise in that situation would have been sex with a man. And after all, you get a pass for that.

There are other hints as well. He has a line about his ass that sounds kinda sus.

“Please my ass”

- Phil Leotardo

The way he orders the body building video turned off. And I hate to bring authorial intent into discussions like this because it ruins the fun, but David Chase has confirmed that all this stuff was intentional.

Now I actually think that most of this is done for humor, and that him being secretly gay isn’t a huge part of his character. But I do think it is related to the main theme of his story arc, which is the death of tradition in the mafia.

You see Phil represents the old school mafioso archetype. He believes in the rules about honor and tradition being more important than anything. Phil is specifically stated to be one of the few guys left that still practices in the old ways, shown by the fact that he did his time in prison quietly.

“You were a man Phil. That’s saying a lot nowadays”

- Butchie

With this in mind, we can see that his hatred of Vito isn't just about homophobia, it's about defending the traditional values that the mob is supposed to represent. In his mind Vito being gay is an affront to their code, and accepting it is tantamount to breaking the rules they are all supposed to be living by.

“In your father’s day, we wouldn’t be having this conversation.”

-Phil Leotardo

Phil also takes the ceremony of the mob very seriously. One of the reasons he has such contempt for the Jersey mobsters is because of their apparent disregard for proper making ceremonies. Again even though logically this kind of stuff doesn’t matter all that much, in his mind this is a denigration of everything they stand for.

“Either it has meaning, or no meaning.”

-Phil Leotardo

The fact that he’s played by the legendary Mafia movie actor Frank Vincent also really contributes to this old school vibe. The show is obviously playing off of his Goodfellas appearance, one of the great mob movies. We’re meant to associate Phil with the classic mob portrayed in older films, contrasted against James Gandolfini as Tony, which is a much more modern portrayal.

This difference is also why Phil comes into conflict with Tony, who despite all his own problems, is something of a progressive in the mob. Though I wouldn't call him an ally or anything, Tony admits that fundamentally he doesn't care about Vito being gay.

“Something inside me says ‘god bless, a salud. Who gives a shit?’”

-Tony

Now again I'm not saying Tony is out there trying to make the mob more inclusive or anything. It's just that he cares more about making money than anything, and to him a lot of these old school rules just get in the way of that.

“What we are here for at the end of the day is to put food on the table for our families, our sons. The future, that’s what’s important.”

-Tony

Part of this is the fact that Phil has been locked away in prison for all this time. He’s literally from a different era, and the world has moved on without him. We see this conflict play out with other mafia guys like Richie Aprile and Feech LaMana, who are resentful of the younger guys who have passed them up while they were away.

The conflict we see between Tony and Phil in the final episodes is essentially a war between tradition and progress within the mafia itself. Will the mob change with the times, or stick to its traditional roots?

Neither philosophy is perfect. We see that the erosion of mafia values like Omerta have led to a rise in informants. No one is willing to uphold the code of silence, and partly that is because no one believes that anyone else is willing to follow the rules anymore.

“But the problem is no one lives it anymore. Not Tony, not nobody.”

-Christopher

Tony's men also recognize his hypocrisy, demanding that everyone else follow the rules that benefit him as boss, while not living up to the principles himself.

“You’re a fucking hypocrite. You preach all this wise guy shit, meanwhile the only one’s who got to play by the rules are us!”

-Christopher

However Phil’s stubbornness and refusal to evolve is what ultimately leads to his demise. After the loss of his brother, Phil refuses to compromise ever again, believing it makes him weak. However when the war creates problems for his men, he refuses any talk of peace as well. His men lose faith in his ability to lead them, and in the end they choose to side with Tony over him.

In many ways, the death of Phil represents the death of tradition in the mafia, both in the story and in a metatextual sense. In the context of the show, the old school days of the mob are gone, replaced with an age of businessmen and informants. Tony himself admits this in the pilot.

“I came in at the end. The best is over.”

-Tony

And on a metatextual level, Phil's demise is a statement about the end of the mob genre. The show serves as a deconstruction of the genre, and there is a reason there really hasn't been another great mob movie after the show ended. There was nothing left to say.

So I hope I've shown you that Phil is much more than just a bunch of jokes. His role on the show serves one of the most important themes we see. And with his focus on tradition and the old school ways, Phil really is the last real mobster.