Pulitzer Prize-winning journalist, author, radio producer, and podcaster Jake Halpern joined Podsauce to unpack the podcast “Deep Cover: Mob Land.” Jake shares how he first learned about Robert Cooley’s journey from a “fixer” to a government informant in the 1980s and invited him to share his story firsthand on the podcast’s second season.
As a mob lawyer in Chicago, a notoriously corrupt city in the 1980s, Robert participated in the system run by power and bribes. The city was overrun with crimes, including mob-related killings each week. Robert was the go-to fixer, representing mob members and guilty criminals, paying judges and using his power to let them walk scot-free. For example, Jake told Podsauce about one of the cases that Robert initially thought was a mob-on-mob killing. The trial received a ton of press coverage, and 2 eyewitnesses testified.
On the podcast, Robert justified his hand in this high-profile case, among others, that let the guilty to avoid sentencing. Robert explained that if a mob killing results from mob business, he does not consider this murder. Later on, Robert learned the murder resulted from a family squabble, as Jake shared in this interview. When Robert realized this puzzle piece, he shared he might not have defended the hitman.
Jake told Podsauce about Robert’s decision to rat out one of America’s most dangerous crime syndicates and work undercover with the feds. He already had plenty of intel to bring down the mob. On this season, Jake allows Robert, federal prosecutors, and those involved to share their stories firsthand. Jake discussed his experiences interviewing Robert for the podcast, likening it to a cross-examination.
We also learned that when Robert first walked into the federal prosecutor’s office and offered to work on their behalf, they were skeptical and could not identify if he had any ulterior motives.
In his 25+ year journalism career, Jake shared why Robert is one of the most courageous people he has seen work tremendously under pressure. Jake highlighted some moments where Robert got most emotional in their conversations.
Now, Robert is now in hiding, and Jake shared how it was possible to finish the podcast under these circumstances, including video calls and visiting his home. Jake explained whether or not he worried about his safety when working on the podcast.