“I know how to get money,” James Grossmann told his brother on the phone one spring day in 2025. His plan, his brother remembers him joking, was inspired by the movie War Dogs, about a couple of down-on-their-luck hustlers who exploit wartime military spending to win a dubious $300 million arms deal with the government. As one of the main characters puts it, “All the money is made between the lines.”
Grossmann needed money — a lot of it. His Boston construction company, Rise Construction Management, was spiraling toward bankruptcy. He was contending with legal battles over $300,000 owed for workers’ healthcare benefits and $35 million in unpaid loans. His brother’s father-in-law also sued Grossmann, accusing him of scamming him out of hundreds of thousands. Amid the upheaval, Grossmann incorporated three mysterious companies 2,000 miles away in Wyoming. He named them Rudiarius, the term for a Roman gladiator who fought his way to freedom.
When later asked about the companies in a court hearing over his firm’s outstanding debts, Grossmann said his Wyoming venture didn’t yet have a purpose. “We don’t know what it is yet,” he claimed.
But according to his brother Chris, Grossmann knew exactly what the operation was for. “That business he owns is a shell; it’s a fake business,” Chris told The Lever — and it was all about making money between the lines. Grossmann denies making the Hollywood reference. But Grossmann, like the “war dogs” in the film, soon used Rudiarius to hustle his way into lucrative government contracts. He has now landed construction contracts to support President Donald Trump’s deportation crackdown worth up to $1.8 billion. In July, The Lever revealed that Grossmann, despite his significant money problems in Boston, had become a key player in the Trump administration’s quest to acquire warehouses and retrofit them into “mega” immigration detention centers.
Now, new court records and interviews with Grossmann’s former business partners pull back the curtain on how fly-by-night operators are scoring unthinkable windfalls from the detention center buildout fueling President Donald Trump’s deportation crackdown. It’s an area that Democrats — newly powerful in Washington after seizing the House and Senate — are likely to focus their oversight, as ICE raids still surge.
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