FBI Infiltrating the Mob: How does It Work?

I am having trouble understanding how the FBI “infiltrated” the MOB (local Mafias).
To wit: the case of ex-FBI agent John Connelly (now on trial in Miami, on murder charges).
In the 1970’s the FBI launched a program to gather information on criminal gangs (e.g. the “Mafia”). To do this, they had FBI agents become friendly with local gangsters, and gain their confidence. The idea was that these gang members would divulge sufficient information, that the FBI could later issue indictments and make arrests-putting the gangs out of business.
In New Jersey, the local FBI guy who did this succeeded brilliantly (Donny Brasco). This guy was a hero-he kept so secret that his wife didn’t know what he was doing-he almost lost his marriage. Anyway, this Agent Brasco got enough information, such that dozens of criminals were caught and convicted-his actions dealt a death blow to the NJ Mob.
In Boston-the very opposite happened! Agent John Connelly (appointed to the FBI without any qualifications (he had been a High school guidance counselor), was set to work with the “Bulger” gang in South Boston. This was a vicious gang, which sold drugs and extorted money from storeowners. The gang murdered anyone who stood in the way(24 murders were attributed to it)., and its murders were spectacularly cruel (one guy was dumped off a boat with a anchor chain wrapped around him).
The thing I don’t understand-everybody KNEW what Connelly was doing-he accepted cash from the Bulger mob, and went on golf trips with the members. One poor dope (an flunky in one of Bulger’s schemes) went to the Quincy Police-who went to the FBI-that poor guy (McIntyre) was later murdered by the gang (Connelly told them who had informed on them).
Connelly retire from the FBI; but later was indicted and is currently serving a 11 year sentence for conspiracy.
My question: how was Connelly supposed to be shutting down the Mob, if he was an active participant in murders and other crimes?

I think you have a few issues confused here. First of all, in regards to Donny Brasco, in New York (not New Jersey), the FBI managed to get an agent named Joe Pistone undercover in the Bonanno crime family. He went undercover as a jewel thief named Donny Brasco, and became a Bonanno associate, and like you said, the evidence he gathered from the undercover investigation helped put a lot of Bonanno family members away, and crippled the family for about 10-15 years.

Meanwhile, in Boston, you had an FBI agent named John Connolly, who brought in Whitey Bulger and Steve Flemmi of Boston’s Winter Hill Gang as informants. They gave him information regarding organized crime that was going on in Boston. It wasn’t until after he retired that it came out that he was also feeding them information on the government’s investigation of the Winter Hill Gang, and receiving gifts from them in exchange for it.

The thing is, the FBI didn’t know what he was doing. They didn’t realize he was receiving bribes and they didn’t realize he was feeding Bulger and Flemmi information about the progress of the investigations against them.

I saw an interview with a guy who they actually wanted to make a “made man”. He said it was money. He set up a shop and gave them watches, electronics and other stuff. They were appreciative and allowed him to get closer. The FBI kept him fueled with money and confiscated goods . He ate with them, partied with them and just kept at it until they accepted him.
He wasn’t even Italian. They thought he was.

Yeah, the Brasco and Connoley exampes were totally different. What I don’t understand about Connoley-he had to make reports to his superiors-when his superiors read the newspapers (and learned of people turning up dead and disappearing), shouldn’t they have had a “little talk” with Johnny? Connoley also socialized with the Bulger criminals-and accepted gifts from them too-was that part of the deal? There are reports that Connoley was receiving so much cash that he didn’t bother depositing his FBI paychecks.
something was very wrong!

Well, they knew that people were being killed or disappearing, but that doesn’t mean they knew that Bulger was using information that Connoly gave him in order to decide who to kill. They didn’t even know for sure that it was Bulger killing all of these people. Remember, when this was going on, the FBI was focusing on building a case against the Boston Mafia, not the Winter Hill Gang, and most of the information that Bulger (who wasn’t the head of the Winter Hill Gang at the time, remember) was giving Connoly was information about the Mafia.

So you had the situation where the FBI in Boston in the '70s didn’t see Bulger as a high priority target, and were happy enough with the information he was providing Connoly that they were willing to not look very hard. And sure, in hindsight, it’s obvious that Connoly’s relationship with Bulger was corrupt and was leading to lawbreaking, but you had to look for it, and at the time, the FBI had no interest in looking for it.

So, none of this infiltrating and impersonating a criminal goes on now, does it not? How have procedures changed to prevent these kind of abuses?

One of the things to remember about most members of a gang or any other organized crime syndicate is that most of them aren’t exactly rocket scientists when it comes to things beyond crime. Sure, some of them are excellent gambling handicappers and can convert grams to ounces to kilograms in the blink of an eye, but beyond a few practiced specialties and what’s known as “street smarts” most of your average Mafioso or Hells Angel or what have you aren’t really all that bright. Sure, they’ll learn some things from being burned, but still, your average member of a crime organization is actually a pretty dumb guy with a propensity for violence and little work ethic, not much more. Not what most of us would consider sophisticated. You don’t need to be when you’re willing to shoot someone in cold blood, that’s usually enough for you to gain some measure of success in the crime world. Very few get by on brains alone.

Now your average FBI agent is normally going to be someone who possesses a law degree and plenty of additional training from the Feds with all sorts of case studies and personality profiles and technical gimcracks and all the time in the world, all of which give them a decided advantage. An infiltration by an agent into a group is then really not much more than out sophisticating them. Given enough time and resources and of course talented and dedicated under cover operatives they will usually get next to all but the most wary criminals.

The Connely case was not really the FBI “infiltrating the mob” it was the mob “infiltrating the FBI”.

An interesting thing that’s a bit hijacky, but- on the wikipedia entry for Bulger it mentions rumors he’s a closeted homosexual who worked as a male prostitute when he was young.

If you mentioned something like this on the page of, say, a sitcom actor and without substantiation- even if you said “there is a rumor that” as a disclaimer, Wiki’s editors would almost certainly remove it. I’ve wondered if it’s a sort of clumsy attempt to bait Bulger (who’s in hiding and on the Most Wanted list) into changing the entry so they can find an IP address. True, it’s doubtful that a 79 year old fugitive checks his wiki that often or would know how to change it if he did, but- doesn’t cost anything I suppose and might help.

Bulger’s one of many inspirations for Hanibal Lecter incidentally, but mainly the Florentine getaway.