You can find UW-Milwaukee graduates working in many of the U.S. government’s three-letter agencies: the NSA, ATF, DEA, even the CIA.
It’s less common for a member of those three-letter agencies to enroll at UW-Milwaukee, but former FBI agent Justin Tolomeo said he’s thoroughly enjoying his time at UWM after a long career with the Bureau.
Tolomeo is the former FBI Special Agent in Charge of Milwaukee, and today he is a PhD student in the UWM History Department. He sat down with the College of Letters & Science to talk about his career with the Federal Bureau of Investigation and how his background has given him a unique perspective in his history courses.
An exciting career
Tolomeo says he grew up in “God’s country,” – “which to me is New Jersey,” he joked. He had always wanted to be a military pilot, but his eyesight wasn’t quite good enough, so Tolomeo switched his major from aerospace to anthropology and joined the Army ROTC at Syracuse University instead.
Upon graduation, though, the Army had implemented a reduction in its officers and Tolomeo was left with a dilemma: What should he do with his anthropology degree? Inspired by law enforcement officers in his own family, Tolomeo became a detective for the Hudson County Prosecutor’s Office before joining the U.S. Drug Enforcement Administration.
Eventually, he transitioned to the FBI, and Tolomeo found the real value of his humanities degree.
“Certainly my degree in anthropology helped me understand people and cultures in a way that I think gave me an advantage,” he said. His liberal arts major also benefited him with the investigative reports he had to write. “(A case) is a story, right? You’re in court, (and) how you organize and present facts is what wins cases and gets you search warrants.”
Tolomeo was first assigned to Chicago. He later transferred to the FBI’s New York City office just a few months before the Sept. 11 terrorist attacks.
“After that, I was working terrorism matters and a lot of financial component analysis to develop cases and networks,” Tolomeo recalled. “That led to me becoming supervisor of these newly-created intel squads, and then going to London, England, for four years as an FBI attaché. My remit was pretty much all terrorism in the UK and Ireland.”
After some time abroad, he was reassigned to the Philadelphia office and finally to Milwaukee.
He was always proud when his work made a difference in the lives of everyday citizens, but the job also came with some perks: “One time I got to meet Buzz Aldrin and Ray Davies from the Kinks. They thought I had a cool job. And I’m like, yeah! My job is pretty cool.”
When he moved to the city, Milwaukee was seen as a “backwater” office. But Tolomeo was soon appointed the Special Agent in Charge, meaning he oversaw all FBI operations in Wisconsin. Under his management, the Milwaukee office expanded, grew in prestige, and handled several high-profile cases.
He helped lead the manhunt for Joseph Jakubowski, who in 2017 stole firearms from a gun store in Janesville, Wisconsin, and sent an anti-government manifesto to President Trump before leading law enforcement on a nine-day chase. Tolomeo also oversaw the kidnapping case of Jayme Closs in 2018. It was one of the last cases he worked before his retirement.
FBI to UWM
He loved his time with the FBI, but the Bureau has mandatory retirement ages and Tolomeo was approaching his after a few years in Milwaukee. He left law enforcement and worked in corporate security for GE HealthCare, but he wanted a more fulfilling challenge.
“I always thought of doing a PhD, but work always got in the way. Then gee, I had more time on my hands,” Tolomeo joked.
Tolomeo enrolled at UWM in 2022. He finished his classes and is putting the final touches on his dissertation proposal. His subject is Dan Smoot, a conservative media commentator active in the 1950s – “kind of the Tucker Carlson of his day,” Tolomeo said. His work examines the influence of Smoot and his impact on Cold War conservative media and beyond. It’s a fitting subject, because Smoot served as an FBI agent before he resigned and became a radio and television host. Thanks to his own career, Tolomeo has special insight into Smoot’s background.
“His FBI file is interesting to see, because he wasn’t a very good agent,” Tolomeo laughed. “He didn’t want to do casework because he wasn’t good at it. … (I) know the Bureau ‘language’ and I understood – they did not like the guy. It’s cool to see it from that angle and understand it.”
Beyond his dissertation, Tolomeo has enjoyed being a student on campus. Taking classes in the History Department has cemented his respect for the humanities.
“I think (in general) there’s been a lack of understanding about government and history. … In a lot of ways, we’ve abrogated (learning) about history, for a whole bunch of different reasons,” Tolomeo mused. He believes it “behooves students to take some history courses. Those social science degrees can be very useful, and they can translate into good career paths in ways that you may not necessarily have thought of.”
After he graduates, Tolomeo hopes to publish his dissertation. Then, he’s considering trying his hand at being an adjunct professor or traveling as a guest lecturer. When he walks across the graduation stage, Tolomeo will officially have gone from FBI to PhD.
By Sarah Vickery, College of Letters & Science