The good agents at the FBI do their best to nail Tony Soprano throughout the course of The Sopranos, some with more success than others.

Despite being pursued by the FBI for years, Tony Soprano is never prosecuted and jailed. That's impressive. According to Tony's own words, it always ends in either of two ways for mob bosses—in jail or dead. Though he is never given a prison sentence, it's still speculated that Tony dies at the hands of the Man In A Member's Only Jacket during those final minutes in the series finale.

Throughout the series, the good agents at the FBI do their best to nail Tony Soprano. They bug his basement and turn several of his associates into informants. None of these tactics worked. But even though the FBI informants fail to incriminate Tony, their actions cause the arrests and prosecution of several other mob members.

10 Carlo Gervasi

It's impossible to root for the homophobic Carlo Gervasi. He exposes Vito's sexuality, causing the mobster to flee to avoid getting killed. And despite being given plenty of responsibility, he isn't good at his job, Tony once complains that Carlo is a poor earner.

Carlo's case is an unfortunate one because he stays loyal for so long only to turn against his colleagues in the series finale. Garlo decides to cooperate with the FBI in order to cut a deal for his son who has been picked up on drug-related charges. Despite his annoying traits, Carlo never gets whacked.

9 Febby Petrulio

Though he only appears in the series for a combined total of 15 minutes, Febby is remembered as the turncoat who gets strangled to death by Tony in the critically-acclaimed episode "College." Tony spots him at a gas station while he is out looking for colleges with his daughter Meadow.

The former mobster ranks low on this list because he had a good thing going in the witness protection program but ruined it. He got himself expelled from the program for dealing drugs. This way, he put himself out in the open, hence Tony managed to kill him.

8 Jack Massarone

Construction company owner Jack Massarone gets played by Tony easily. The mob boss orchestrates a protest in Jack's company, forcing him to seek the DiMeo family's help in stopping it. Tony promises to stop the protests if he gets a cut of the business. Jack agrees but becomes disgruntled. He eventually begins snitching.

During his meetings with Tony, he wears a baseball cap. However, Jack isn't confident enough, so Tony gets suspicious. Tony ultimately orders a hit and Massarone's body is found in the trunk of a car.

7 Eugene Pontecorvo

Eugene's career as a made man is decent until his dead aunt's will names him as heir to her fortune. His wife sees no need for him to continue to be in the mafia so she begins pressuring him to quit so that they can move to Miami and live a peaceful life. He makes the request to Tony but Tony declines.

It soon emerges that Eugene is working with the FBI too. After Ray's death, the feds also prevent him from moving to Miami so that he can help them build a case against Tony. Feeling trapped, Eugene takes his own life.

6 Jimmy Altieri

Capo Jimmy Altieri's short stint as an informant mostly stems from the fact that none of his seniors like him. When a corrupt FBI agent tells Tony that Big Pussy is snitching, Tony thinks the agent is confusing Pussy with Jimmy, since the two have similar body shapes. It doesn't help that Jimmy keeps asking too many questions, making Tony suspect him.

The FBI agent dies without Tony confirming who he meant, so he concludes that Jimmy is the informant and not Pussy. It turns out that both of them are indeed working for the FBI. Jimmy is eventually killed by Silvio and Christopher who first taunt him by telling him to ask for help from his FBI friends via his wire.

5 Larry 'Lorenzo' Barese

Lorenzo is often portrayed as a reserved and humorous member of the DiMeo crime family hence it comes as a surprise when it's later revealed that he is an informant. The head of the Barese crew helps the FBI locating the body of a murder victim who was killed by Tony over 25 years ago.

Not much character development is given to Lorenzo, making him the average informant. Interestingly, Anthony Borgese—the actor who played Larry Barese- was a real-life member of the Gambino crime family. He served 6 months under house arrest after being found guilty of extortion.

4 Salvatore Bonpensiero

Big Pussy is the show's most popular informant. It takes a couple of years before any of his colleagues discover that he is working with the FBI. It would have remained this way for a while, had Tony not gotten a weird dream suggesting that Big Pussy was ratting.

The character initially does a good job of covering his tracks. He even kills a fellow mob member who spots him talking to his FBI handler. And when he disappears for a while, he lies that he had gone to a foreign country to seek treatment. In his last days, he begins to enjoy his secret job a bit too much and starts pursuing suspects like a cop. He is fun to watch. Sadly, he doesn't make it past Season 2.

3 Jimmy Petrille

In the Season 5 finale, it emerges that the consigliere has been an informant since 1981. Since events in the episode take place in 2004, Petrille's status as a rat stretches across 23 years. That's quite impressive. Petrille's cooperation gives the FBI plenty of meat to enable them to go after Lupertazzi underboss Johnny Sack.

The police raid Johnny's house when he is with Tony. Luckily, Tony manages to escape. Tony then learns that Petrille was the snitch but he never gave up any information on the DiMeo family. Petrille never gets killed for ratting either, so he gets bonus points for that. It's alleged that he went into the witness protection program.

2 Adriana

Adriana ranks highly in this list because the FBI tries so hard to get her to cooperate but fails. First, the bureau uses a female agent to befriend her but this plan fails when Christopher hits on the agent, causing the friendship to crumble. The FBI then brings Adriana in to make her cooperate by force but she avoids giving the agents any meaningful information.

When she is threatened with a prison sentence for covering up a murder, she still refuses to cooperate. Instead, she comes clean to Cristopher. This act of loyalty ought to have made the DiMeo crime family spare her. Instead, Christopher tells Tony who orders Silvio to whack her. It's a sad end to such an intriguing character.

1 Raymond 'Buffalo Ray' Curto

Ray takes the top spot because he is so careful that his snitching activities never ever get discovered by his fellow mobsters. He dies with his secret when he suffers a stroke in an FBI agent's car.

Given his age and numerous appearances, it's possible that he manages to give the FBI plenty of incriminating information. His motivations for ratting are never revealed though it's suggested that it has to do with his son's expensive treatment. Ray had to be on the outside so that he could keep earning and pay for his son's medication.

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