It's a simple question but I think it will elicit lots of conversation and maybe even debate. There have been many era's in the lifespan of the mafia in America which is why I decided to ask for two favourites. Mine come from the same era.

Vincent "Schemer" Drucci - Laurence Bergreen, in his book, Capone: The Man and the Era, describes Drucci:
"He had a streak of recklessness and daring, and he looked the part of a gangster – tough, dark, and menacing, his expression frozen in a tragic mask topped by wild unkempt hair (and) a face to haunt the dreams of his enemies."

And

Jack "Legs" Diamond - In 1930, Diamond's nemesis Dutch Schultz remarked to his own gang, "Ain't there nobody that can shoot this guy so he don't bounce back?"

They both were killed in a hail of gunfire. 'The Schemer' by a cop and 'Legs' got 3 in the head while hiding out in Albany, NY. Both were rebels in that they resisted what came to be known as "The Commission". I guess I have a soft spot for rebels.. Who are your two favourite gangsters and why?
-Joe The Boss

1) Willie Marfeo: not really a gangster, just an illegal bookmaker. I like him because, when extorted for money, he had the balls to give Tameleo a slap on the face calling him an asshole, and told him to tell Patriarca to sh#t in his hat. In the 60s that was a 100% death sentence, therefore it was a stupid action not to go into hiding after this, yet it's impressive nevertheless, imo.

2) Carlo Caputo (boss of the Madison family): never really bothered anyone, no massacres or high-profiled murders on his turf, just quietly stayed at home without paying taxes.

Carmine Galante: Ruthless, cold to the bone, larger than life, one of the most menacing and feared gangsters.

Louie "Haha" Attanasio: Listing this guy soley based on his nickname. He would laugh every time he heard about a mobster dying.

According to one of his drivers who was interviewed in old age by Rose Keefe, Drucci's idea of a good time was to stand outside a cafe dressed as a priest, wait for a couple to walk by, and say "nice ass, honey", and when they turned around shocked, he'd say "not you lady, your fella". Then sometimes Dean O'Banion would show up and pretend to angrily kick the shit out of the "priest" to shock people even more. Sounds like a real fun bunch.

probably an un popular choice......but sammy the bull. the guy just looks like a fuckin menace in his early days. I don't care what anybody says, so what if he ratted. he did what was in his nature to do. and that was to fuck someone over before he got fucked. half these punk asses calling him a rat think they are cool but really...the guy has a 20 head body count I believe.

do we really only have to list two? oh well i'm listing more:

frank costello - lets face it. the guy had swagger...

roy demeo - not only was the guy a vicious killer...but a good earner. I mean...the guy went out like a boss. he knew what fate awaited him and he accepted it. the whole gemini crew really. the twins are scary as hell.

Anellio dellacroce - a mans man and all round gangster believed in the life like no other


Giacomo tocco - anyone who has been in charge of a mob family since 1979 deserves massive respect . He is the longest sitting mob boss in the country and he and his family has been largely untouched

I think Carmine Persico, Carlo Caputo, James Lanza and Stefano Magaddino have been bosses longer than Tocco.

I was talking about sitting mob bosses , caputo , maggadino and Lanza are dead . Granted carmine persico has prob been boss since the early 70s but he has been out of prison 4 years since then

Casso > bull

Jimmy Burke (Conway) - For his short temper, wildness & brain. He was the guy who brainstormed the infamous "Lufthansa heist", afterwards cutting the loose ends of his action. Also, for the way he's been greeting Dominick "Remo" Cersani when he's been already dead and buried on the back of "Robert's Lounge" - "Hey Remo, how ya' doing?". James was pretty crazy, however, he shared with his profit with his family.

John "Sonny" Franzese - For being the 100% real mobster. He's the oldest Mafia member that lives, currently. He's 96 years old, if I'm not mistaken. Just imagine, if he'd speak out loud about what he had done in the past, or talk about any connections/stories he knows. It's a damn history! But knowing his personality, perhaps he'll keep this all only for himself, taking to the coffin.

Jack Tocco is a great choice. It's true, he is the 2nd longest sitting boss behind junior but he hasnt been in prison all but 4 of those years and his family decimated by the feds and warfare.

maybe it will be in spite of persicos reign, but the colombo family is still gonna be around long after Detroit is defunct and gone.

I would've thought judging by your name that Joe Masseria would be one of your choices haha.

Frank Costello - A decent and reasonable man by mob standards who had a great mind for that way of life and focused on profiting over warring. My thinking is that if he wasn't involved in that line of work then he would've prospered in the world of legitimate business.

Bugsy Siegel - May not have been the most smartest but to me he's the definition of a bad ass and boy what a life he lived. One thing that fascinates me to no end is the fact that he had met Benito Mussolini, Joseph Goebbels and Hermann Goering prior to the second world. He was connected to Mussolini through a countess he was having an affair with and wanted to sell Mussolini weapons. He apparently disliked Goering and Goebbels' Nazi ideals and the way they carried themselves so much that he was compelled to have them killed which would be a stupid idea judging by the positions those two men held.

I also want to mention Joe Masseria whom i don't necessarily like but have a lot of interest in.

Gotti Sr = Big Balls

Tony Accardo = genius

Nicholas Civella low key boss who made KC a powerhouse .

Joseph Bonanno at 26,became one of the youngest bosses of a crime family,had a nice 30 plus year run.

Mr Neil was a hardcore gangster and planned the Galante hit. He was feared and nobody dared to cross him.

Joe Batters was a stone cold killer and one of the leaders of the outfit for 50 years and never spent a night behind bars.

Lansky and Luciano. Old school

Not sure I would call my 2 favorites "gangsters"...

Jo Jo Pecora - Johns choice to succeed him but a date in Lexington, KY kept that from happening.
Joe would have been the "Peoples' Boss". A really good guy.

Charlie Murgie - Maybe the mold for all Consigliere! Charlie had vision while all the rest wore bifocals!

I would also say giacomo tocco , the longest sitting mob boss in the country on the street , how he has gone untouched all these years and has adapted to the times is a testament to the influence and respect he weilds , mob bosses years ago never had to deal with rats , Rico , wiretaps and other FBI scrutiny and he is still around , there as only ever been one rat in the family so that shows the respect he has , it also goes to show that if you stick to the traditional mob staples the Feds pretty much leave u alone , the Detroit mob is set up the same as the Genovese family the administration is well insulated with captains acting as a ruling panel on the street , it must work the Detroit mob and the Genovese family are amount the most successful families in the country and have the fewest rats

Agreed- the unofficial leaders of the Italian and Jewish syndicates at one time. I'd add in Costello and Siegel, even though the thread asks for 2.

They were closely aligned and were connected in many high profile rackets and major events: Ending the Castallamarese War, Havana gambling, organizing the mob meetings in Atlantic City and Havana, the Flamingo, WWII, high level political connections, Murder Inc, the set up of Genovese, the possible whistleblowers for Apalachin, developing drug routes, Louisiana slots, Hollywood, etc...

Russell Bufalino- Had his own, quiet family but yielded as much power as any boss in the country.

Charles "Charlie Murgie" Imburgia (LaRocca Crime Family)- I have to agree with Friend of Henry. Arguably, one of the most powerful Consigliere's in the country. He still mediated disputes and was a voice of reason between many of the Midwest crime families until the age of 92. He died in 2002, but was so low profile while owning his pizza parlor "The Sunrise Inn" that nobody advertised what he truly was...but the people who needed to know, knew.

Owney Madden ~ One of the original commission members, present at the Atlantic City 1929 conference. Owner of the Cotton Club, Texas Guinan's, The Stork Club etc. One time leader of the original Hell's Kitchen gang "The Gophers". Retired to Hot Springs, Arkansas in 1935 and took over all political power in that state for the next 30 years. *Yes you can blame him for Clinton but in his lifetime few saw as much change and lived to enjoy it. His career literally went from the turn of the century gangs of new york to modern day organized crime and he died very comfortably in bed.

Moe Dalitz ~ Purple Gang member, Mayfield Road Mob, king of Las Vegas, The Desert Inn, The Stardust and Rancho La Costa. Literally no major arrests, served honorably as a captain in the US Army during WWII, Las Vegas Man of the year every time you turned around. Again another Mob guy who really knew how to play the game and win...every time.

Ray Patriarca Sr - IMO Ray Sr is easily one of the most successful mob bosses of all time. the whole "Father Fagin" thing where he fixed his way out of the joint is legendary too. there was no one close to as powerful as him in new england which i think is a big reason things got so ugly when he passed.

Tony Accardo - pretty much all the reasons listed. no way you can't respect his reign.

i gotta throw an honorable mention to sonny franzese and larry zannino, two real old school hitters who never ratted (or in sonny's case, never will).

http://en.wikipedia.org/wiki/Billy_Hill_(gangster)

https://www.google.co.uk/#q=murray+humphreys

Murray Humphreys Chicago.

Billy Hill London.


Two men died peacefully, all about making the money, pure class and not much jail time.

Tony Accardo because of the power he had and yielded. Also the respect he demanded and lets not forget the fact that he ran the Outfit for 50 or plus years. During Accardo's reign, the Oufit was at its most powerful and wealthiest.
The other is John " No Nose" DiFronzo. Despite the fact that I have met him and have talked to him, he is shown great respect and made his crew wealthy. Also escaping prosecution after being named as one of the killers in the Spilotro killings is something that should be noted.

Accardo ran the Outfit for 50 years and plus? 20 years maybe?!

Edit reason:Fuck even 20 years...

Dead:
1) John "Johnny Dio" Dioguardi. One of the best labor gangsters in history. Scammed up until he died, I love gangsters that never retire.
2) Jimmy "Brown" Failla. Had his hands in everything. Shoulda been replaced Gotti if that hit went through.

Living:
1) "Uncle" Joe Ligambi. Best run as a boss (acting, whatever) since the old school guys of Carlo, Lucchese and the bunch.
2) Alphonse "Allie Shades" Malangone. Man was/is a garbage God.

I'll never forget what "The Cigar" said in prison to the black man on the phone. Not going to repeat what he said but that little guy had some balls.

I would also add a 3d favorite gangster: Harry "Santa Claus The hunchback" Riccobene. It's interesting how he stood up against Scarfo and almost managed to become an independent boss under Bruno, except for symbolical gifts. Also, if people were to be judged from physical appearance, then Harry would be the most inoffensive gangster in the world

Appearance wise little Harry didnt look like much but he was a real gangster i mean Wayne Grande shot him what 5 times and then Harry took the gun and beat him up