Obviously if anyone reads my posts mine is Gaspipe, but I have a few others.

Carmine Persico: Lived 70 percent of his life in the can and still is head of a Mafia Family.

Fat Pete Chiodo: I guess maybe cause little is known about him.

Matthew Maddona: probably becuase he was connected with Nicky Barnes and even at 70 plus years old, he still is active with the bloods and crips in NYC. That amazes me. There was a story once how he was seen in the Ghetto hanging out with the Bloods and playing dice with them! And this was recently.

Joe Massino: I dont think ANYONE really realizes the weight his name carried from about 1970 til his arrest.

The entire Decavalcante family: The sopranos connection, they kind of legitimized the Sopranos for me.

Fat Tony Salerno, he has a classic mafia don looks. Fatt and with old school clothing and not to mention fedora and sigar

And of course Tony Accardo, the best mafia leader in my opinion.
Not a single day in jail, and extremely wealthy and died peacefuly still in power.

Gaspipe: Incredibly smart, amazing earner, turned down being boss and basically influenced/controlled Amuso as underboss, carried out hits left and right, went on the lam for 2 years from the feds while also running the family/ordering hits AND coming into nyc to have dinner with his ruling panel, a lethal mobster through and through, gets screwed in the end by the feds after flipping, and regrets flipping to this day. This guy was a lethal/rich mobster.

Wild Bill Cutolo: charismatic, great earner, running/creating businesses left and right, i have read about how lots of people who ran shops didnt mind paying protection to him cause he was a classy guy and really loved his neighborhood, did lots of charity work, hitman for the colombo family and a heavy hitter during the colombo war, when him and his crew were swept up by the feds and jailed at the MDC he led a crew prayer through their separate cells and prayed for their release,beating trials, health, families, and for LCN. They eventually were acquitted of charges relating to the war. Had entire dinners with his crew almost every day at his club. Went to the sitdown with Allie Persico even though he suspected he wouldnt come back (confirmed by a close Bonanno Capo who he had lunch with), his remains are found years later and takes down the family administration as a final payback.

Gotti Sr - loved his style, media personality (even though that was his downfall) he was a calculating guy who literally loved his close friends dearly (hear it on wiretaps,) ordered hits on guys he suspected were rats or unloyal, and fought the feds tooth and nail, was defiant until the day he died.

Sonny Franzese - living legend of la cosa nostra,great earner, very famous/popular in his time, around during the persico and gallo wars/era, sentenced to 50 yrs for a crime he didnt commit, constantly violated parole to meet his buddies, stand up guy through and through, deadly hitman (killed over 10 guys from his own words picked up in wiretaps,) even at 90 plus years old he was still shaking down strip joints, both his sons flipped and hes still around.

Carmine Persico- the Snake is a lethal mob boss who since his side murdered Joe Gallo and days after Joe Colombo was shot has been the defacto boss of the family even in jail, Persico's name has been mentioned in dozens of murder-cases since then, as he has been in charge of the Colombos for over three decades. During his 50-year-membership with the Colombo crime family, he has survived three internal wars, his life sentence, and allegedly been shot more than 20 times. Persico is also only one of three defendants from the Mafia Commission Trial who received 100 years and is still alive.

For Me it would be Roy DeMeo.
The guy who was a perfect family man and the neighbour from heaven hosting barbacue's and 4th July parties for his neighbourhood yet at "work" he was the devil himself.
Leading one of the most atrocious crews in Mob history.
A terrific earner and a nasty killer.

Another intriguing guy for me is Tony Mirra although not much is known about him other than he was a nasty bastard and an accomplished killer who even other wise guys feared - he also once took part in group sex involving an up and coming young hollywood actress (rumoured to be Goldie Hawn!)

Gerrard Pappa although again not to much is known about him but he did once clip a guy whom he despised and just for good measure he buried the body under the foundations of a new building taking care to ensure the victims head was placed exactly underneath where the toliet would be!!!!!!!!!

Carmine Persico as others have said obviously has something about him to still be a boss after all these years - he's been a major mob figure for years and years

jerry anguilo. Sentenced to 45 years at age 67 and he out lived the sentence to walk free in 2007. Impressive. Was able to build a gambling empire so large that he sent $50 K a month down to raymond patriarca during the 1950's even more impressive. Made bostons north end the safest place to live in the state during his reign as boss the most impressive. RIP jerry

I will name one from each family:

(1) Frank Costello (Genovese) - The guy had political contacts like no other. He was a gentleman.

(2) Aniello DeLacroce (Gambino) - He had honor like no other.

(3) Matthew Madonna, Aniello Migliore, Joseph DiNapoli and Steven Crea (Lucchese) - I have said it on this board and I will say it again. The Lucchese family is poised for a massive power play. These guys have been around forever. They have street cred and some carry over from the days of Tommy Lucchese. We will not know for sure until Crea is eventually brought down, but I believe the guy may become the most influential mobster in the NY area with the backing of the ruling panel.

(4) Persico (Colombo) - For the same reasons stated above.

(5) Joe Bonnano - If anyone deserves it from this family, it is him. He never went crazy. He was omnipotent up to a point and retired on his own to spend time with his family. He was also intelligent. Watch some interviews if you doubt it.

I agree with you on Crea and crew the Lucchese family is probably raking in the dough quietly, Crea hasnt been in the headlines at all since his parole expired a few years ago. They are all old school guys leading the family...

The cops didn't screw him, he screwed himself by being a paranoid killer and a rat.

Jackie DiNorscio, although sentenced to 30 years for drug trafficking, he refused to testify in the famous 1988 trial that lasted 21 months, he could, burying the jersey faction
Joe Gallo brave and cruel, was the first to realize that times had changed and that to make more money, we had an alliance with blacks, especially with Nicky Barnes,
Matthew Madonna, did business with heroin was sentenced to 30 years in the 70s although it was a simple associate does not wish to testify, released in 1995, three years later he became a man of honor of lucchesse.

I agree with the choice of DiMeo.Roy was a great worker, he controlled 90% of pornography with the DeCavalcante family in the late 70s, big drug dealer, ruthless killer, with his gang is believed to have killed 75 to 200 people. Given that Castellano did not trust him, he made sure that the Gambino signed an alliance with the Westies, so that the boss was forced to introduce it, was killed in 1983 because he considered unmanageable by Big Paul, who knows what he would do with Gotti, would perhaps , became great friends.

The cops screwed him cause they didnt want him to testify and doubt claims that Gravano had stated and by extension jeopardize their conviction against Gotti. He is a paranoid killer and a rat.

Casso would probably be my first choice. The guy was a huge earner and seemed to have his hands in so many things. He was on good terms and did work with high ranking members of other families like Frank DeCicco, Greg Scarpa, and even got to meet the Chin a few times. I also find him running the family while being on the FBI's most wanted for over two years to be fascinating. His time at the top was during a very volatie time during the history of the mafia.

Greg Scarpa Sr would be another one. He was another nut job, and he also worked for the FBI on big cases like the Civil Rights case in Mississippi. He had to have a lot of interesting stories.

There are other guys out there too, I just have to think about it for a while.

I don't understand this fascination with Casso. He was a sociopath who happened to be in the Mafia. I personally find the figures who were not purely homicidal maniacs but were capable of restraint to be far more interesting. These individuals are the ones that separate LCN from the Mexican Cartels or the Bloods and Crips and allow them to be romanticized.

Casso was in the mafia, not a social worker. Homicidal maniac is an over used when mafia members are discussed. The vast majority of people they kill or intend to kill are people part of the life, it's not like they are serial killers trolling the streets for innocent people. The fact that he was a huge earner and had his hands in so many different rackets makes him interesting to me. He also had the mafia cops working for him, and was on the FBI's most wanted list for over two years while he still ran the family from the NYC area. Outside of one or two people Casso wasn't killing random citizens like the Bloods & Crips, and the Mexican cartels. He was being fed legit information on rats, and people who weren't showing proper respect to the family. I think any mafia boss or member would have no problem "doing away" with these types.

You are correct in stating that he was a "huge earner" and it is impressive(?) that he was on the Most Wanted List while he ran the family for a considerable period of time. The Mafia Cops are also an intriguing facet of his life.

But you know what is more interesting? Being a bone fide boss and spending little to no time in prison. I think his presence on the FBI's Most Wanted List attests more to his lack of ability as a "boss" than anything else. You say "outside of one or two people Casso wasn't killing random citizens." I say that killing one or two random people is sufficient to classify you as a paranoid sociopath when you have murdered many others who are not random. Yes, the vast majority of Mafia figures (probably) have murdered. BUT they are not insane like Casso, Anastasia or Gravano. No matter how hard you try to argue otherwise, there is a distinct difference between the aforementioned individuals and people like Carlo Gambino. Gambino murdered when he HAD to. Compare his life to Casso's. Yes, Casso was not a social worker. However, he is also a far cry from the Gambinos of LCN. He and his Crony Amuso can enjoy their days in jail and will hopefully garner the negligible respect they deserve when people look back.

neil dellacroce was one intriguing figure. he was a guy who could have been boss easliy if he used forced but he was a mafia loyalist. The only mistake he made was helping John gotti rise to the top. I think most people would agree that without dellacroce Gotti would have never been made. In a sense he inadvertanetly killed the gambino family by helping Gotti become a powerful figure.

I think Dellacroce (whom I am vastly intrigued by) further supports my argument against Casso having any virtue whatsoever. Mr. Neil was ruthless in his day, but his life was more than dictated by Omerta and he would never think to break ANY rules. Casso was ruthless, but had no rules. He killed numerous members of his own family, he killed civilians, he killed anyone. He was paranoid because he killed so much and...he killed more. A guy like that is not what LCN is about. Mr. Neil, not renown for his mercy, killed as well, but was not absolutely mad.

You have to take into account Casso's entire body of work, not just those last few years of absolute craziness. He built himself into one of the most respected and feared gangsters in NYC, if not the entire country. You also can't compare a boss from the 80's- early 90's era to pre RICO old timers like Carlo Gambino. The government had much more resources and powers to combat the mafia starting in the 80's then they ever had before. If those bosses from back then were alive in the 80's, they would most likely have faced major prison time too. The Vincent "Chin" Gigante went to and died in prison, does that make him less of a boss? I don't believe it does, because the deck was stacked against him, the Government wanted to send him to prison, and that is what they did. All bosses went down during that era, do you guys like Salerno or Tony Duck's were not good as bosses because they went to prison too? So you just can't point the finger at Casso for being on the run from the FBI, he was actually the only boss to go on the run, and stay free for a couple of years.

Most mafia members killed are almost always killed by their own family. Casso was killing guys who were rats, and guys who weren't respecting the boss. You would expect any legitimate mafia member to do the same. There were times he went overboard though. You can't expect a boss to allow soldiers to not kick up, not report, and nothing happen though. The only civilian killed by Casso was Nicky Guido, and that was a mistaken identity. They also attempted to kill the sister of Pete Chiodo, who was a bummeling idiot.

Giuseppe Morello - A true Leader, a fucking war horse. This guy knew how to win a battle and was utterly ruthless. Great at strategy and power plays. Ran a massive counterfeiting ring in the late 1800's and early 1900's. If it wasn't for him going to prison joe the boss would have never rose to power.

Carmine Lombardozzi - A fucking genius with numbers. When it comes to shylocking and running stock scams no one came close to this guys power. Stolen Securities...carmine was the biggest fence for that shit in the country. Tremendous earner and leader.

Tony Accardo - If you really want to see how a boss should act look at how accardo ran the show. Stayed in the shadows, played it smart but still ran shit. Accardo could be as cold as ice and stick a ice pick into someones heart but also could be reasoned with. A true diplomat.

Roy Demeo - A fucking ridiculous earner. This guy could juggle 15 different scams at once. Had the business sense and also the killer instinct. The guy you sent to do the dirty work and you knew it would get done right but also the guy you could trust with important business stuff.

Murray Humphreys - Amazing fixer. This guy could grease any hand, Had connections that rivaled costello's. This is definitely the guy you would want to handle the business and political end of things.

Dont forget Sonny Black, great earner loyal to the boss. And when he knew he fucked up and was going to get killed. He accepted it and went straight into his end.

Murray Humphreys. Why? Because he was one of the first mobsters, if not the first to popularize the "taking the Fifth" to avoid self-incrimination. He was a mix of menace and smarts. The Hump was able to stay at the leadership level of the Outfit for years and along with people like Costello is probably the best real life example of a wise consigliere.

Humphrey's Oklahoma house

Many gangsters who I find intriguing are already mentioned by others.

Tony Accardo, Joe Bonanno, Carlo Gambino, Joe Massino etc.

But I would also like to add both Rizzuto's, Nicolo and Vito.

These guys were almost the perfect mob bosses and incredibly smart and cunning, which are ofcourse the most important qualities a boss needs to have.

They were also real gentleman with a certain style and charisma.

Both were also 'bridgebuilders'. Nicolo built up a huge network which he used as a base for setting up an incredibly effective organization. He laid the foundation, and his son Vito solidified it by making many alliances. Both father and son were also perfect mediators.

I'm speaking in the past sense because Nicolo is recently killed and Vito is locked up in prison. And since it's now turmoil in Montreal it looks lke his days are over. I'm really wondering what Vito Rizzuto will do when he returns, if that would happen in the first place. It's most likely he will be out of the picture as others have filled the power vacuum he left behind.

The big question is: will he still have allies left and be able to pull some strings? We will see.

I go with Costello because he was truly the iron fist in the velvet glove. His political sophistication really gave organized crime a license to steal.

Costello is also a good one.

It was rumored that J. Egdar Hoover didn't want to recognize the existence of the mafia because of his friendship with Costello.

He is, ofcourse, also one of the major characters were Vito Corleone is based on.

1.Sal testa- The crown prince of south philly in the early eighties. He was a capo at 28 an his was a true leader. 2. Joe Ligambi, anyone who can put the philly mob back together like he did is a true leader,plus i met him several times down the jersey shore when i was younger working at a club in margate. A true gentleman. Everyone calls him 'uncle joe'.

I thought they DID kill Fat Pete's sister?

In September 1991, using a wheelchair due to his wounds, Chiodo testified in the Windows trial. Chiodo stated that he had undergone a "transformation" from a violent criminal to a man with a conscience. When asked what prompted this transformation, Chiodo replied "I was shot 12 times,".

Chiodo's remaining family in Brooklyn soon suffered retaliation from the Luccheses. On March 10, 1992, Lucchese associate Michael Spinelli shot Patricia Capozallo, Chiodo's sister, while she was driving in Bensonhurst. Capozallo suffered wounds to the arm, back and neck but survived. On February 2, 1993, the body of Frank Signorino, Chiodo's uncle, was found in the trunk of a car in East New York. The body displayed several gunshot wounds to the head.

Chiodo provided valuable evidence that helped convict both Amuso and Casso as well as many other gangsters. He had to be flown around in a special plane while a witness because of his weight.In July 1997, Chido testified against Genovese crime family boss Vincent Gigante in another Windows-related racketeering trial.

On September 11, 2007, Chiodo was sentenced to 17 years in prison on racketeering charges but will serve no prison time due to his agreement to testify.Chiodo is currently in the Witness Protection Program.

Don't forget that Vito may have to stand trial in Italy for the bridge money laundering scheme. It's quite possible that he will be extradited to face those charges.

Joey Massino is another good choice. He saw a lot of stuff happen during his time with the Bonnano's. He was a member when Galante got out, and eventually killed. He was involved with the killing of the three capos. He was involved in the killing of Sonny Black. He was a member through the Donny Brasco fiasco. He was also able to pick up the pieces and make the Bonnano's a force again as its boss, up until he became a government witness.

James "Jimmy" Burke, not a made guy but had a lot of respect. He was close to some powerful figures like Paul Vario, never backed down from anyone, and was a major player in the Lufthansa heist.