Sopranotember: In Praise of Phil Leotardo

The Shah of Iran is far more fascinating than his one-liners.

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There’s a quote from 30 Rock where Jack Donaghy tells Liz Lemon that ‘life is about minimizing regrets’. Phil Leotardo, the last boss of the Lupertazzi Family and played by Frank Vincent, is probably who the quote was referring to. Because he will tell you that he did twenty years in prison, mentioning that three times throughout the show: first when Johnny Sack pled guilty and admitted in a trial that he was a mafia boss. Then, when tells his right-hand man Butchie this after ranting about his own family name. And finally, when he was belligerent during his final sitdown with Tony Soprano, he tells how he compromised during his time. All of this is wrapped up around a shell of regrets and misbegotten grudges. 

I knew that Phil Leotardo would be my favorite character before he was even introduced. The Sopranos had many colorful characters, but no one was more colorful than Phil. He makes Livia Soprano look like Barbara, in comparison. If you visit any Sopranos clip on YouTube, the comments section is saturated with riffs of his quotes or the ‘shinebox’ scene where Frank Vincent played Billy Batts in Goodfellas. While he was more famous in that small, but brutally battered role, Phil is his signature performance.

Phil was s a larger-than-life figure when he was introduced in Season 5. He was loyal to John Sacrimoni, despite their differences; Johnny would be friendly with Tony when it calls for it. Phil isn’t and would break off with Johnny because he cried at his own daughter’s wedding while being arrested by the FBI. He would eventually become a main feature in Season 6A and 6B, being the new boss for the Lupertazzi family. His approach was old-fashioned, more senior to Tony, who is approaching middle age. Given the show’s running theme of decline, it seemed appropriate and made sense that in the scheme of things, Phil could bring wisdom to the family, because it sorely needed it after the death and absence of Carmine and Johnny respectively. Phil’s tendency to throw personal tirades is a personal feature and in a nutshell, that summarizes his narrative arc. 

Phil’s anxieties begin, not with the slain killing of his kid brother Billy (he was 46) from Tony’s cousin Tony Blundetto, but with his family lineage, which he believes was cursed by choice. You see, Leotardo wasn’t originally his family name, but a deliberate misspelling of Leonardo once his grandparents immigrated to America. There’s a sacrilege upon that name, rather than Leotardo, which refers to a tutu.

Pride defines the character of Phil, so there’s little emotional middle to be had. The only time he did restrain himself, was thinking of taking out Tony at the end of Season 6A, but won’t, because such an act has always been frowned upon. That is remarkable, because, before this - once he whined about being called the Shah of Iran - the peace negotiations between the New York and New Jersey families fell through as soon as Little Carmine mentioned Billy. After this, he suffered a cardiac arrest, to which Tony, convinces him to relax from his duties and focus on his own family. Otherwise, Phil takes things very personally and would not move on with general business once that issue has already been resolved. Not only couldn’t he let go of Billy’s murder, but he cannot get over the fact that Vito Spatafore, who he loved as a brother-in-law, is gay, even after he murdered him. This also caused his demise, as he expresses disappointment in Butchie, his most loyal soldier who shares every motive to take out Tony but could not do it in the quickest timeframe. 

It enables him not to act rationally upon negotiations and sitdowns. Add to that is the New York mafia having further utility than the New Jersey crew, hence there is a lot of use for Phil, while he sees Tony as inferior. The asbestos and the vitamins are quite impossible to manage, but the one thing that sets off the dynamic between the two, was when Phil owed Tony money over the new horse track. In the episode In Camelot, there is a car chase where Phil throwing out ice cream, while Tony blares Rock the Casbah, that is filler but establishes everything we need to know about him.

There are irritated characters in The Sopranos who could compete with Phil. Like him, Richie Aprile was pissed off after he was immediately released from prison and died of a headshot. Livia Soprano will go to great lengths to be annoyed at anything. However, Phil remains likable and one of his redeeming qualities is his sense of humor, which as a result of his passions, enables him to deliver memorable one-liners or insults. He also arrives with many friends due to a glistening reputation as a soldier.

Phil is also a walking jokebook and steals almost every scene he’s in. That makes a lot of sense because before Frank Vincent was a regular for Martin Scorsese, he worked alongside a comedy act alongside Joe Pesci, who you see being beaten by him in Raging Bull and Goodfellas, and the other way around in Casino. Vincent was the straight man to Pesci’s nuisance, according to his New York Times profile, and Phil was basically a role designed for Pesci. So it isn’t surprising that even when Phil becomes incredibly emotional, there’s usually a line or moment that makes me laugh. This comes in two angles. The first comes with juvenilia. One of the funniest moments was Phil yelling at Tony and Little Carmine from the top of his house as if he’s an insulting Frenchman from Monty Python and the Holy Grail. This permanently destroyed their relationship. The second is a bit of gallows humor. Leotardo requires Vincent to be incredibly vulgar in a simple, but contemptible manner. One example of this is him delivering “I guess the turd doesn’t fall far from the faggot’s ass”, referring to, of course, Vito.   

Phil and Tony Soprano do have kinship, regardless of how unlike each other. Both share the idea that the world has moved on and have not grappled with the effect they currently have over their crew. As we see Tony become more cruel and irredeemable, we see Phil almost go through the same path just like him, only for his prison years to delay this further. But he grapples that the norms he grew up with - gun and sword as part of inducting made men, which Phil claims Tony didn’t do, even though they actually did - aren’t there, and weren’t there. That’s probably why Tony expresses pessimism about the state of affairs with the DiMeos in the first episode. Because the values of honor - to which one of them Phil believes is serving time in prison - is fading away, Phil was released at the most inevitable and worst time period possible. 

Phil was symbolic of the worst that is yet to come for Tony and makes things far more difficult than they needed to be. But they were both made for each other. Because life isn’t simply about limiting the shame of making terrible decisions, it’s also the ability to compromise. And that’s the thing Phil regrets the most.