By 1927 Orgen was branching out into new fields. He had befriended Jack Legs Diamond who was one of Arnold Rothstein's top guys. Legs made a handful of trips to Europe as part of Rothstein's narcotic ring. Diamond was letting Orgen in on some drug deals and, in return, Little Augie was letting Diamond into the labor rackets. This didn't sit well with Orgen's chief lieutenants Lepke Buchalter and Gurrah Shapiro who were losing money on the jobs that went to Diamond.
Lepke and Shapiro decided that their boss had to go. Orgen had an appointment to meet Diamond on the lower eastside. Diamond showed up and met Orgen and the men began to walk. A sedan followed them. After a bit, a number of gunmen got out of the car and ran up behind the two gangsters. Orgen was shot in the head. Legs turned and was shot in the stomach. This was to neutralize him. They wanted him dead he would have been killed outright like Orgen.
The gunmen jumped back in the car and sped away. Diamond picked himself up off the sidewalk and staggered to a nearby hospital.
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