He was associated with several high-profile public enemies during his criminal career, including Harvey Bailey, Albert Bates, George "Machine Gun" Kelly and Baby Face Nelson.

[3] Little information is known of his early life; however, most accounts agree that Eddie Bentz was born in Pipestone, Minnesota (or South Dakota) on June 2, 1894.

During 1932, he began teaming with Albert Bates and George "Machine Gun" Kelly, robbing a bank in Ponder, Texas on July 31 and another in Colfax, Washington on September 21, taking $70,000 in cash and bonds.

Bentz went into semi-retirement after that job and was living in Long Beach, Indiana, when he was approached in 1933 by George "Baby Face" Nelson to join him and his gang in planning the robbery of a bank in Grand Haven, Michigan.

John Dillinger was widely speculated to have been one of the participants; however, historical evidence indicates he was involved in bank heists on his own in Indiana and Ohio at the time of the robbery.