A new HBO documentary series is exploring a fascinating but often overlooked investigation that exposed a multi-million dollar fraud at the heart of McDonald’s Monopoly games — an investigation Fairhope resident Douglas Astralaga found himself working as a young agent fresh out of the FBI academy.
“McMillion$” chronicles how the FBI used a fake film crew, numerous wiretaps and assistance from McDonald’s corporate office to bring down a criminal operation that diverted more than $24 million in cash and prizes to dozens of handpicked “winners” between 1989 and 2001.
Astralaga worked as attorney for six years prior to joining the FBI in the late 1990s, and because of his legal experience, his most prominent role in the McDonald’s case was something coworkers described as a “thankless job.” As the Title 3 administrative agent, it was Astralaga’s job to process all of the paperwork that had to be filed in court for the FBI to legally wiretap the phones of key targets in its investigation.
It’s not work that’s made for TV, but without it, the case would likely have never gotten off the ground. The hoops Astralaga guided investigators through were also essential to making sure the information that agents and federal prosecutors spent months gathering would ultimately be admissible in a criminal trial.
“My main job was more or less making sure the legal rules of the wire intercepts were followed,” Astralaga said. “I understood the legal issues and could work with the U.S. Attorney, so that if a question came up we were able to determine, ‘Oh, yeah, we can do this’ or, ‘God, no! We can’t do that.’”
In the early stages of their investigation, agents knew several of the biggest winners of McDonald’s Monopoly game were related or had other ties to one another. Something wasn’t right, but they didn’t know what, and they were concerned asking too many questions might alert the fraudsters.
Special Agent Doug Matthews, a friend of Astralaga who is arguably the star of “McMillion$,” came up with the idea of agents posing as a film crew shooting a commercial for McDonald’s to question the winners. It was an unorthodox approach that required the fast food giant to participate and to run its Monopoly game again, knowing it was compromised, in hopes of catching the perpetrators red-handed.
In the second episode of “McMillion$,” Astralaga’s former supervisor says he was brought in on the undercover operations as a “reward” for the legal legwork he was doing behind the scenes. In his first appearance, Astralaga talks about pretending to be a lighting technician on some of those fake film crews.
It was “a lot of fun,” but 20 years later, he still doesn’t know what a lighting meter does.
“Oh, I had no idea what I was doing,” he told Lagniappe. “But the benefit of [those interviews] was that in an investigation or prosecution, there’s almost nothing better than locking somebody to a story, especially if that story is inconsistent with the facts that you know. And … this was all on film.”
Investigators were able to compare statements in those interviews to what they already knew and what those same “winners” previously told McDonald’s about how they found their winning game pieces. Eventually, the investigations came to focus on Jerome Jacobson or “Uncle Jerry” — the head of security at the marketing company McDonald’s hired to develop its Monopoly game and paid to run it for years.
Among other things, “McMillion$” details how Jacobson was likely the only person who could have possibly penetrated the otherwise robust system of security measures Simon Marketing and Dittler Brothers Printing developed to ensure the integrity of the McDonald’s Monopoly game.
In the end, the FBI’s investigation led to more than 50 indictments detailing a sprawling conspiracy that involved mobsters, strip club owners, drug traffickers and Mormons that cost McDonald’s more than $24 million. Though it can be complicated to follow, the investigation is truly fascinating. However, despite its various entertaining elements, the case is one that seemed to fall from collective memory.
That is likely because the first 21 criminal indictments were publicly unsealed on Sept. 10, 2001.
“It was a big case — a huge case at the time, but it did lose some of its luster because of 9/11,” Astralaga said. “Understandably, the FBI pretty much put all of its resources and focus on that threat of terrorism.”
Astralaga was the lead legal counsel for the FBI’s Mobile branch from 2006 until he retired in 2019, and his segments in “McMillion$” are shot on location in the local office. As someone who has served as a media coordinator during events that drew national attention, Astralaga isn’t a stranger to the camera.
Still, he said working with HBO’s documentary team was a unique experience for him.
“This was a top-shelf type production. These guys were very capable and they’d done all of their research as well,” he said. “You can see it in the final product. It’s very good, and it captures the essence of the personalities of the agents, which you hardly ever see in anything that an agent is willing to do.”
Despite having roots in the Northeast, Astralaga still says coastal Alabama is “home” for his family. He currently works as the general counsel for 68 Ventures in Daphne, which is the parent company for numerous real estate and development entities that operate in coastal Alabama and the Florida Panhandle.
“McMillion$” airs Mondays at 9 p.m. on HBO. The first three episodes of the six-part series are also available to stream online, and the network has also created a companion podcast with additional interviews and untold stories that releases weekly episodes on all major podcast platforms.
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