When reading many profiles on wiseguys such as Carmine Galante, Roy DeMeo, and Albert Anastasia... whether they were bosses or just street soldier thugs, all are described as ruthless cunning killers that were extremely feared in the mobs underworld. My question is, who do you think was the TOUGHEST or MOST ruthless cold hearted of them all? I only listed a few but after your answer go ahead and list others that are on the top 10 list in your eyes.

From what I've read, Carmine Galante was a real ruthless bastard. But Anastasia is generally credited with at least 50 murders.

Carmine made the Bonannos the most drug infested family in N.Y. and probably all over the U.S.

Genovese and Anastasia were ruthless. Anastasia especially. And if Genovese didn't get an underling to betray Anastasia he surely would have been taken down in the war against the Mad-hatter. Genovese knew he couldn't get a good night sleep having Albert as an enemy.

I'd go with Carlo Gambino or Meyer Lanskey they combined their ruthlessness with courage and especially, brains.

From what I've heard I would say Vito Genevese is one of the most ruthless. Either him or Anistasia.

I also think Anastasia in America but I think Riina is the worst.

Yeah Riina (sp.) was pretty bad. I rememeber reading a long time ago that he whacked a teenager who was the child of someone in the Italian government. He got life though I think..

Who is Rina? And what Family did he run?

He was a boss in Sicily. For the exact name of the family you'd probably have to ask Turnbull or T.G. There was an article in Time or Newsweek (don't remember) that had his story. His full name was Salvatore "Toto" Riina I believe.

the most ruthless gangser hands downs was AL CAPONE

All those italian gangsters are nothing compared to the russian gangsters when it comes to being ruthless.

Don Salvatore ‘Toto’ Riina, aka"U Curtu", aka "La Belva" was born in 1930 in Corleone, Sicily. He came in the family of Luciano Leggio (he also was very ruthless). Riina was the Capo di Tutti Capi from..(i don't know..somewhere in the late 70's of 80's) till 1993.
Tomasso Buscetta (a Sicilian don) turned informer (pentito). Judge Falcone started a war against the Cosa Nostra. In 1992 Falcone died by a bomb placed in the highway/road.
In 1993 Riina was arrested.
From http://glasgowcrew.tripod.com/riina.html
Riina became a victim of his own arrogance, thinking that he could dominate the state rather than co-exist with the state. Toto Riina is serving live behind bars his underboss Bernardo Provenzano is now head of the Cupola..

The Cupola is the Sicilian Commission.
I think Riina was in the corleone-family (sounds familiar ) Because in Sicily, the name of your family is the name of the town from the family.