Hymie Weiss was born Earl Wajciechowski in his homeland of Poland in 1898. He emigrated to the United States with his family and the name was changed soon after their arrival. Weiss became buddies with Dion O'Banion in his teens and the two of them together performed numerous burglaries, car thefts and jewel robberies. They also worked together in the news paper wars where they would muscle vendors to sell only the papers that they represented. The years went by and Weiss became O'Banion's right hand man in the ruthless North Siders gang. The gang became involved in bootlegging and had frequent run ins with Al Capone and John Torrio, the Italian mobsters who would eventually rule the city.

Some crime experts have credited Hymie Weiss with building up O'Banion's booze empire. He was smarter, had more vision and was more resourceful than the hot headed Irish mobster relying much more on bribery and forced reasoning than O'Banion ever did. He also coined the phrase "a one-way trip". In 1921, a fellow gangster called Stephen Wisniewski hijacked some of O'Banion's booze and Weiss was tasked with the job of teaching Wisniewski a lesson. Wisniewski was invited to go for a ride with Weiss along Lake Michigan and, somewhere along that ride, he was whacked. Weiss is said to have stated "We took Stevie for a ride, a one-way ride!"

After the murder of Dion O'Banion, Weiss became the Boss of the North Siders and began plotting the demise of those responsible for the death of his good friend - namely Torrio and Capone. Weiss kept a low profile for two months after O'Banion's funeral and then on January 12th, 1925, made an attempt on Capone's life. Weiss, Schemer Drucci and 'Bugs' Moran tailed Capone's limousine to a restaurant on 55th Street and State where they opened up with their guns and managed to get 26 hits on the limo. The chauffeur was hit but Capone and his two body guards were unscathed by the tirade of bullets. Weiss then tried a hit on Torrio in a similar manner and bungled that too. Torrio's dog was killed along with his chauffeur but Johnny escaped with just two holes in his Fedora.

Weiss made a second attempt on Torrio and was a little more successful this time. On January 24th of the same year, Torrio was ambushed outside his apartment block and was gravely wounded by shot gun blasts and .45 caliber slugs from Weiss and his accomplice, 'Bugs' Moran. The two hit men were about to apply 'la coup de grace', a shot to the head, when they heard an approaching vehicle. Thinking the oncoming vehicle to be police or worse, other members of Torrio's gang, the two of them fled. The vehicle was actually a laundry truck. Torrio survived and after two weeks in hospital retired from the gang.

Weiss continued to try to get Capone. Probably his most famous attempt took place outside Capone's headquarters, The Hawthorn Inn in Cicero. Weiss had a whole cavalcade of cars drive past the Inn and fire over 1000 rounds into the building on September 20th, 1926. One of Capone's bodyguards and an innocent woman bystander were hit but, once again, Capone was unhurt.

Three weeks after the Hawthorn Inn hit, Weiss was killed by a Capone hit team. An unknown gun man was lying in wait in the second floor window across the street from Weiss' headquarters - Dion O'Banion's old flower shop. The gun man opened up on Weiss and three of his men with a machine gun. Weiss was DOA at the hospital and the coroner counter 10 bullets in his body. He was 28 years old when he died.