The Sopranos is full of trigger-happy and remorseless gangsters, but Phil Leotardo manages to stand out even in that environment. Shortly after coming out of prison, Phil rises to become the don of New York’s Lupertazzi Crime Family, thanks to the death of Carmine Lupertazzi and the imprisonment of Johnny Sack.
During his stint as boss, Phil establishes himself as Tony Soprano’s greatest foe. Credit can be given to Tony for always trying to be friendly to him. Unfortunately, Phil’s hard-boiled personality prevents him from settling for anything less than bloodshed.
“The Sopranos Are Nothing More Than A Glorified Crew.”
Phil’s opinion of the DiMeo Crime Family, led by Tony, is never high. Tony’s efforts to extend an olive branch a couple of times prove futile. The Lupertazzi boss is craving war and isn’t interested in peace treaties. Towards the end of the final season, he orders hits on all of the senior members of the New Jersey mob, letting his crew know that they’ll do business with whoever’s left.
As a result of Phil’s directive, Tony’s brother-in-law Bobby Baccala is murdered at a toy store while Consigliere Silvio Dante is ambushed by gunmen while driving, leaving him in a coma. Despite these setbacks, Tony proves that the Sopranos aren’t just a glorified crew. They eventually give Phil the most brutal murder in the series.
“Anybody Ever Die In Your Arms? Give It Time. See If I Can’t Make That Happen For You. “
Tony Soprano’s cousin Tony Blundetto is initially reluctant to rejoin the mob when he gets out of prison. Sadly, the poor economic state of his pockets shoves him right back in. And while he is back in the game, he makes the mistake of killing Phil Leotardo’s kid brother Billy in retaliation to the murders of Lorraine Calluzzo and Jason Evanina.
Tensions escalate between New York and New Jersey, leading to a sit-down involving Tony, Johnny Sack, and Phil Leotardo. To no one’s surprise, Phil’s mind is filled with nothing but the need for vengeance. He asks Tony if a loved one has ever died in his arms. When Tony says nothing of the sort has happened, Phil implies he can make it happen for him.
“My Estimation Of John Sacrimoni As A Man Just Plummeted.”
According to Phil, mobsters are supposed to be so tough that their tear ducts ought to remain shut at all times. When Johnny Sack cries as he gets whisked away by the feds at his daughter’s wedding, Phil can’t help but lambast him in front of his colleagues.
It all starts when Sack, who is in jail, makes a special request to attend his daughter’s wedding. At the ceremony, the feds guarding him declare that time is up before he even gets to see his daughter ride away with her husband. This causes Sack to burst out in tears in front of everyone. Tony sympathizes with him because he has a daughter, too, but Phil sees it as a weakness.
“I Wanted Manicott’, But I Compromised. I Ate Grilled Cheese Off The Radiator Instead.”
The Lupertazzi and DiMeo families clash once again over a business deal involving the illegal dumping of asbestos from a building project. Phil demands 25%, but Tony feels it’s too much because his own crew spotted the opportunity. A level-headed Tony tells Phil to be logical about his decisions because feelings come in the way of financial feasibility.
Once again, Phil refuses to compromise. His streak of tough stances is influenced by the fact that he spent two decades behind bars. He explains how he ate bad food in jail but never complained. Now it’s his turn to eat well.
“You Don’t Ever Admit The Existence Of This “Thing” Ever!”
In other Sack-related matters, Phil loses his mind when he watches a news report about the former head of the Lupertazzi Crime Family admitting that he is a member of the Cosa Nostra. Johnny Sack also pleads guilty to 47 RICO predicates and is sentenced to 15 years plus a fine of $4.1 million. Thanks to his admission of guilt, the feds are ordered not to seize all his assets.
Phil doesn’t see this as a win for Johnny Sack’s family. He is infuriated over the fact that Sack admitted that the Cosa Nostra exists. His feelings are somehow understandable since he himself spent 20 years behind bars and never talked. Sack’s actions are understandable, too, because he is simply looking out for his wife and children.
“Cooler Heads Prevailed.”
The statement is ironic because Phil says it right after he chases Tony away from his property. Once again, Tony sought to make peace over the fact that he had pistol-whipped Lupertazzi street soldier Coco. Tony had every right to do so since Coco had harassed the New Jersey mobster’s daughter Meadow while she was on a date.
Little Carmine tries to initiate a truce between Tony and Phil, but the New York boss refuses to sit down. He instead orders both Tony and Carmine to leave. An angry Tony drives off, and when Little Carmine asks him what he just did, he says he did the right thing.
“Next Time There Won’t Be A Next Time!”
A change in leadership doesn’t always sit well with everyone, and that’s the case for loan-shark Lorraine ‘Lady Shylock’ Calluzzo. She refuses to make payments to Johnny Sack when he takes over as the new boss after Carmine Lupertazzi’s death. An angry Sack thus sends a newly-released Phil to collect.
Phil performs a mock execution on her using a gun with no bullets. He then gives her time to get the money and promises her that the execution will be very real next time.
“Guys There Don’t Get Their Finger Pricked. There’s No Sword And Gun On The Table.”
In order for aspiring gangsters to become “made guys” (official members of the mafia), there is normally an oath ceremony. The chosen few get to perform several rituals, such as holding their hands over fire and drawing blood. This is best seen in the episode where Christopher Moltisanti becomes a made guy.
Trust Phil Leotardo to feel that the New Jersey crew doesn’t even get this ceremony right. While having a chat with his street soldier Albie, Phil criticizes the DiMeo family once again, claiming that they initiate gangsters who don’t deserve it and conduct the ceremony in a cowardly manner.
“Let Me Tell You A Couple Of Three Things.”
Phil’s plan to take out the entire leadership of the DiMeo Crime Family is an ambitious one. Members of his inner circle aren’t too sure about it when he tells them. Upon sensing their doubts, he gives them a detailed recap of how much Tony has offended him.
His intention is to tell them Tony’s three major sins, but he ends up saying a lot more. Though Phil is clearly aggrieved, most of the problems he has with Tony are things that can be talked out. It is often obvious that his hostility stems from a personal dislike of Tony and not any serious issues.