Weiss was born in Poland and brought to the U.S. age of three. He became part of
Dion O'banion's gang and was believed to be the one to steer the gand into bootlegging. Weiss was more cool headed than his boss and would reportedly attempt to calm O'banion down during one of the bosse's outbursts. One of Hymie's greatest "accomplishments" came in 1925. Along with
George Moran, Weiss leapt out of his car and began shooting at Jonny Torio's car, then followed Torrio up the stars where they put five non-fatal shot in the rival boss. While the hit did not kill Torrio, it did send Jonny into retirement. After O'banion was killed Weiss eventually took over the North Side gang and became a dangerous threat to
Al Capone. Weiss and Capone fought one of the bloodiest wars in Chicago gangland history. Each attempt on the others life more extravagent than the last. Capone, who was ready for peace, setup a meeting where they would work out a treaty. Weiss was still angered about the murder of his boss O'banion and demanded that the trigger men be killed. Capone refused the deal and the war was once again in full swing. Then on Oct. 1926, as Weiss and three others stepped out of their car, Capone's men met them with a fury of gunshots. Weiss was left dead with tren slugs in his body. Though Weiss lost the bloddy war, he was said to be the only man Capone ever feared.