The Chicago Outfit

Chicago Poor

How did Bob Cooley become the insider who destroyed the Chicago mob and the 1st Ward? We start at Bob’s youth on the South Side of Chicago, as he details his childhood struggles and the murders of both his grandfathers. Both men were cops, one ironically killed by Al Capone's hitmen.

Left For Dead

Bob becomes a Chicago cop and applies his street smarts to rise rapidly through the ranks. His encounters at the criminal courts inspire him to go to law school, but his world is shattered when he's left for dead after being run over by a patrol car. This is the third and final pillar of Bob's youth, as the foundation is set for his journey into Chicago's underworld.

• 38:18 Mob Police

Chicago’s Courts

The malfeasance in the Chicago courts inspires Bob to go to law school. Mob-connected cop Rick Borelli introduces him to the web of illegal gambling operations that reach into the western suburbs of Chicago.

• 18:33 Rick Borelli Mob Cop
• 22:21 The Mob Gambling Machine

Count Dante And The Purolator Heist

A strange character named Count Dante enlists Bob for legal help. The Count is being charged with murder for an attack on an opposing dojo whose owner is siphoning his clients. Bob finds himself entangled in the Count's bizarre world, which he has to break away from. After the Count's mysterious death, Bob discovers evidence that he was involved in the Purolator Armored Express Heist. The crime remains unsolved and at the time was the largest cash heist in the US. Bob also discusses the Chop Shop Wars and an accumulating body count that follows him.

• 40:43 Mob Cremations
• 52:35 Mob Fences
• 56:30 Police Mob Referrals

D'Arco, Marcy & Aleman

This conversation propels us into the inner sanctum of Chicago’s 1st Ward. A shadow government within a government that controlled the state of Illinois. Two men operate the levers of power, both of whom started as gunmen for Al Capone. One is John D’Arco Sr. who needs Bob to take his wayward son under his wing and teach him how to be a lawyer (despite him being a state senator). The other is Pat Marcy, a man of near-mythical proportions who had the presence of a stone-cold killer. Marcy needs Bob to fix the Harry Aleman trial. Aleman is a hitman who’s been charged with murder, and his trial becomes unprecedented legal history.

• 12:09 The Mob Created The Laws

Fixing Murder & Marcy Power

Carol Jean DiPasalegne was murdered by her husband, but the 1st Ward fixed the case so her husband would walk free so the machine could steal the insurance money on a double indemnity clause. Bob also explains how Pat Marcy gained control of the 1st Ward and exerted his ruthless power.

• 25:48 Michael Corbitt Mob Cop

The Chinese Mob (Chicago Style)

Bob is introduced to members of Chinese organized crime by Chicago Alderman Fred Roti. A few members of the Ghost Shadows are pinned for a murder and need Bob's help. This begins a new chapter in Bob's life that takes him to the East Coast and an underworld of Chinese mobsters stretching from Manhattan to Boston.

A Crisis Of Conscience

At the behest of Pat Marcy, Bob defends a man accused of assaulting a female cop. Bob's encounter with Marcy after the trial is the spark that sends him to visit the Organized Crime Strike Force and turn on the 1st Ward. We also touch upon gambling operations at the local horse racing tracks in the Chicagoland area.

• 30:00 Mob Sheriffs With Guns

The Beginning Of The End

Growing frustrated, Bob begins to build his own cases against the 1st Ward and the Chicago Outfit. He wears a wire on Pat Marcy and hatches a plan to bring down Johnny D'Arco Junior by passing legislation for a bribe. There's also a sting operation that goes sideways in Wisconsin when Bob and the FBI set up some mobsters with the opportunity to rob a $1 million poker game.

• 25:38 The Mob Robbery