Mine would have to be hands down Tony Accardo. It's been said that Tony Accardo had more brains before breakfast than Al Capone had all day. They didn't call him Joe Batters for no reason. He was a soldier/muscle for Capone and its been said that even Capone thought he was a scary individual. Capone gave him his nickname Joe Batters and he also apparently saved Capone's life on a couple occasions. He went on to become what I would say the biggest, longest running, and most powerful boss in Chicago's history of Organized Crime. I'm pretty sure even though Giancana, then Aiuppa were labeled Boss he was always the Boss. Just used Giancana to be the face of The Outfit because Giancana loved the limelight. Aiuppa was also a very smart and good Boss. Together him and Accardo pretty much ran Las Vegas from Chicago. Of course along with other Outfit leaders from Kansas City, Milwaukee and Detroit. In my opinion he was probably one of the most powerful Bosses in the history of Organized Crime. Hands down my favorite!

Hey your new here(so am i basically)so i dont mean to mess with you but this seems like a real fanboy question that i and a lot of other people here tend to stay a way from, with that being said i gotta go with the chin, him wandering around greenwich village in a bathrobe pissing all over the sidewalk lmfao. Hes the reason the geneveses are the most secretive and powerful family today.

Thanks for the heads up Dellacroce. I found this site awhile back and just decided to try it out. I started it off with as you a real fanboy topic and I now know thanks to you my friend that its a topic to stay away from. I appreciate the heads up.

Accardo was great. However, He was not the Boss during Giancana's reign. Giancana was the Boss because of his Taylor St. Power Base, pure and simple. He did not take orders from Accardo.
Ricca & Accardo were Advisors. Ricca was Giancana's sponsor into the Outfit and mentor.

Big fan of the important cogs who never made a ton of noise:

Ross Prio(CHI), Carmine Lomardozzi(NY), each had more money than most wise guys could earn in 5 lifetimes

Pat Marcy's real name was Pasquale Marchone. He changed it and reigned over the 1st Ward of Chicago for over 3 decades, and when they finally found someone in his inner circle to flip...he died during trial an old man.

I could go with the obvious and rattle off a bunch of the most notorious guys there were, but I'd rather post a few slightly obscure names and see who else were fans of the quite guys as well

also the guys who ran the zip crews, people like Patsy Conte who built up their power by aligning with the italian mobs in sicily and bringing guys over. Not to mention their confusing success in the heroine trade, a business that 90% of their counterparts to this day can't very successfully figure out who longs periods of time

Ross Prio, a fucking Powerhouse Boss. Boss of the North Side /Rush St. Crew until his death in 1972. A multi-multi millionaire back in those days. Dominic DiBella, Dominic Nuccio, Dominic Brancato, Jimmy Allegretti, Vince Solano, Joey DiVarco were all strong made guys that belonged to Prio. He also owned some big Dairy or Cheese Company that was legit.
Was very loyal to Ricca & Accardo.

Chin

Is it true Ross Prio was an Outfit 'torture specialist'? Or that he was consulted on every murder contract before it was commenced?

Meyer Lansky would be my favorite

Joseph Zerilli.....and ill say this just to make some ppl mad around here and that is...Salvatore Lucania

joseph j.r. russo one of the most respected gangsters and one of the gangster of gangsters. He was the go to go guy sort of speak during old man ray's time and he was respected all over the country. second would old man ray himself and third neil dellocroce

Don Vito

Jo Jo Pecora - Ptttsburgh LCN

Carlos Marcello. I'm a southerner and he and Trafficante were the only southern powers in LCN. Trafficante's Cuba days are fascinating as well, but I love New Orleans and Marcello COULD'VE altered history as we know it with JFK.

Roy DeMeo.

Vincent Gigante.

Carlo Gambino hands down turned the family into a power house in less than 20 years.

Dominick Napolitano.

'Hit me again and this time do it right.'

Best there never was.

Do you believe that shit I saw on tv I think it was Phillip Carlo the author of true crime books says .."Carlo jumped up ans said "FROGGY LEGS"

I think that shit is made up..is froggy legs mob slang

My favorite of all time? Mistakes and all, it would have to be Sam Giancana.

When he walked into a room, there was a sense of power and self confidence I never saw in any other person EVER in my life. He was a true Mafioso. He would come over to the house and see my father occasionally. He lived in Oak Park, we lived in River Forest. I never went to his house. My father always went there alone.

He had balls bigger than the United States. That was actually his downfall when he returned to Chicago. He let his guard down. He still thought he was invincible.

He was always nice to me and actually asked me questions about school. I was just a kid but I knew he was special in some way. He actually liked the Beatles, But preferred Sinatra and Dean Martin. He even somehow arranged a few of us kids to see the Beatles Concert at Comisky Park in 1965 even when he was having a lot of legal trouble.
He was one of the most loyal straight forward men you would ever meet. There was nothing phoney about him.

He was very generous with his men and valued them. All his men had fat bellies (very large amounts of money). He would NEVER betray a friend. He had some real good qualities that outweighed his bad qualities.
He had a good heart for his friends. He feared noone.
As tough as he was, he had trouble handling his daughter Antionette. She was a big problem for him.
Life for my family was never the same when Mooney left. I know most people think he is burning in hell, but I'd like to think his generous heart and loyalty to his friends saved him.

My vote goes to al capone, the only mobster outside of new york to go to new york and clip one of thier captains (frankie yale) without fear of retaliation, if u was capones enemy u was' nt safe anywhere!