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This article was originally published by The Lever, an investigative newsroom. If you like this story, sign up for The Lever’s free newsletter.

Last summer, business was looking bad for hotshot Boston developer James Grossmann.

His flashy new construction company, Rise Construction Management, had begun to spiral into financial ruin. That June, a bank sued Grossmann when he failed to repay a $25 million loan — just one of a mounting number of lawsuits he and his firm were facing from frustrated creditors.

Amid allegations of unpaid invoices, fraud, and evidence tampering, Rise laid off more than half its staff and watched its ambitious development projects collapse. It was a cautionary tale for the city’s flagging commercial real estate industry, Grossmann told local press.

But as Grossmann’s company fielded more than a dozen lawsuits and he tried to salvage his reputation, his name began to appear in connection with far more lucrative dealings: Immigration and Customs Enforcement (ICE)’s massive spending spree on real estate for “mega” detention centers.

Earlier this month, the Department of Homeland Security purchased two prisons from CoreCivic, one of the world’s biggest private prison companies and a longtime ICE detention contractor. The deal was massive: The government bought the two facilities for $1.5 billion. In a public notice to its investors, CoreCivic disclosed the name of the agent working with the Department of Homeland Security to close the deal: James Grossmann of SK2, LLC.

Community Activism Forced Federal Government to Abandon Plans for ICE Warehouses

It wasn’t the first time Grossmann’s name had surfaced in connection with the Department of Homeland Security’s real estate dealings. As grassroots research group Project Salt Box reported this spring, the developer played a role in at least two of ICE’s purchases of massive warehouses, which, under former Homeland Security Kristi Noem, the agency planned to retrofit into detention centers.

The Lever reviewed court documents, federal contracting records, and business filings to piece together how a Boston developer went from financial peril to playing a central role in billion-dollar deals for the Department of Homeland Security. The end result is a striking glimpse into the opaque contracts and enormous windfalls that are buttressing ICE’s buildout of its detention apparatus and the shadowy operators who are using President Donald Trump’s immigration crackdown to build — or rebuild — their reputations.

As The Lever revealed this spring, the Department of Homeland Security’s strategy to buy up detention infrastructure could help it evade state and local oversight. But there has also been speculation that ICE’s warehouse deals — which have cost another $1 billion-plus in taxpayer funds — were designed to shore up a struggling commercial real estate industry. As More Perfect Union reported, the Department of Homeland Security bought the warehouses in some cases at double-digit premiums, even as demand for large warehouse property dwindled.

Politically connected real estate brokers, meanwhile, got their own cut of the deals.

Reached by phone and asked about his connection to ICE’s prison deals, Grossmann said that he worked “on real estate” and conducted environmental site assessments. Although he did not dispute that his name appeared in connection with SK2, he said, “I don’t have a contract working with them.”

Grossmann did not respond to The Lever’s additional inquiries. SK2 also did not reply to a request for comment.

Before Grossmann was a struggling developer — and ICE contractor — he was a high-powered construction executive. He spent two decades at Suffolk Construction, a large Boston construction company, working his way up to become chief operating officer. Then, in 2019, he struck out on his own, founding Rise and announcing a series of splashy new development projects around the city — luxury condos and state-of-the-art biotech research labs.

Over the next three years, Rise saw rapid growth. One........

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