Episode 328 Jack Ruby Miniseries Part 4

In the pre-World War II era of the "Chicago Cowboy," Jacob Rubenstein was a striking figure of manic energy on the West Side. Working out with desperate intensity at local YMCA clubs, he obsessed over his physical conditioning and receding hairline, famously boasting to anyone who would listen that he could "hit harder than Joe Louis." Struggling to stay afloat after the tragic murder of his labor union mentor, Jack teamed up with business associates to launch the Spartan Novelty Company. Operating out of cheap, transient hotel rooms, they chased the cash-heavy flow of "punchboards"—unregulated, highly addictive, gray-market gambling devices that were sweeping across the country.

When the bombs fell on Pearl Harbor, Jack's deeply emotional patriotism spurred him to manufacture patriotic plaques and plaster busts of his idol, Franklin D. Roosevelt. However, his own perfectionistic psychology sabotaged the dream; his obsessive-compulsive design delays kept the products in development for months until cheap, mass-produced competitors flooded the market, leaving him completely broke once more. But as his commercial novelties fell apart, a much more physical struggle was brewing. Confronted by the rising local threat of the pro-Nazi German-American Bund, Jack and a crew of tough young Jewish brawlers from the Lawndale Pool Room mobilized, taking pool cues and heavy wooden clubs directly to the fascists’ street rallies to defend their community with primal ethnic pride.

This high-voltage era highlighted the ultimate Jacob Rubenstein paradox: he was a volatile, quick-tempered brawler, yet he acted with a deeply ingrained sense of chivalry. The same man who would crack heads at a Nazi rally was also a self-appointed protector of the weak who violently beat college students for hurling racial slurs at a Black piano player, and threw himself into a savage street fight to rescue an older woman being abused by a stranger. This riveting chapter of Jack's life draws to a close in May 1943 when the street hustler of Roosevelt Road is finally drafted into the U.S. Army Air Forces—setting the stage for a surprisingly disciplined military career that would be punctuated by explosive, defensive violence.