{"id":1263,"date":"2026-07-31T20:10:55","date_gmt":"2026-07-31T20:10:55","guid":{"rendered":"https:\/\/smartmovinghome.com\/?p=1263"},"modified":"2026-07-31T20:10:55","modified_gmt":"2026-07-31T20:10:55","slug":"this-developer-went-from-financial-peril-to-billion-dollar-deals-for-dhs","status":"publish","type":"post","link":"https:\/\/smartmovinghome.com\/?p=1263","title":{"rendered":"This Developer Went From Financial Peril to Billion-Dollar Deals for DHS"},"content":{"rendered":"
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Read more Israel and US Ridiculed for Reportedly Considering \u201cLand Blockade\u201d of Iran<\/a><\/p>\n<\/div>\n<\/div>\n

Last summer, business was looking bad for hotshot Boston developer James Grossmann. <\/p>\n

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 \u2014 just one of a mounting number of lawsuits he and his firm were facing from frustrated creditors.<\/p>\n

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\u2019s flagging commercial real estate industry, Grossmann told local press.<\/p>\n

But as Grossmann\u2019s 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)\u2019s massive spending spree on real estate for \u201cmega\u201d detention centers.<\/p>\n

Earlier this month, the Department of Homeland Security purchased two prisons from CoreCivic, one of the world\u2019s 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.<\/p>\n

It wasn\u2019t the first time Grossmann\u2019s name had surfaced in connection with the Department of Homeland Security\u2019s real estate dealings. As grassroots research group Project Salt Box <\/em>reported this spring, the developer played a role in at least two of ICE\u2019s purchases of massive warehouses, which, under former Homeland Security Kristi Noem, the agency planned to retrofit into detention centers.<\/p>\n

The Lever <\/em>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\u2019s buildout of its detention apparatus and the shadowy operators who are using President Donald Trump\u2019s immigration crackdown to build \u2014 or rebuild \u2014 their reputations. <\/p>\n

As The Lever <\/em>revealed this spring, the Department of Homeland Security\u2019s strategy to buy up detention infrastructure could help it evade state and local oversight. But there has also been speculation that ICE\u2019s warehouse deals \u2014 which have cost another $1 billion-plus in taxpayer funds \u2014 were designed to shore up a struggling commercial real estate industry. As More Perfect Union <\/em>reported, the Department of Homeland Security bought the warehouses in some cases at double-digit premiums, even as demand for large warehouse property dwindled. <\/p>\n

Politically connected real estate brokers, meanwhile, got their own cut of the deals.<\/p>\n

Reached by phone and asked about his connection to ICE\u2019s prison deals, Grossmann said that he worked \u201con real estate\u201d and conducted environmental site assessments. Although he did not dispute that his name appeared in connection with SK2, he said, \u201cI don\u2019t have a contract working with them.\u201d<\/p>\n

Grossmann did not respond to The Lever<\/em>\u2019s additional inquiries. SK2 also did not reply to a request for comment.<\/p>\n

Rise and Fall<\/strong><\/h2>\n

Before Grossmann was a struggling developer \u2014 and ICE contractor \u2014 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 \u2014 luxury condos and state-of-the-art biotech research labs.<\/p>\n

Over the next three years, Rise saw rapid growth. One glowing profile in the local press in 2022 remarked that \u201cthe young company must be doing something right.\u201d Grossmann and his business partners were projecting revenue to triple to $150 million within the year.<\/p>\n

But by the fall of 2023, Rise began to quietly collapse. Since 2021, the company had been slowly accruing lawsuits from a fleet of subcontractors who said they hadn\u2019t been paid, and that fall, the property owner of a condo project Rise was working on realized something was amiss. <\/p>\n

In January 2024, the property owner sued Rise and accused the company of a \u201cmassive fraudulent billing scheme.\u201d Rise had allegedly been accepting money from the owner to pay the project\u2019s subcontractors, but instead putting it toward other unrelated expenses. In April, a judge awarded a $20 million judgment in favor of the property owner in the case.<\/p>\n

In April 2024, a different property owner said in court that Rise had \u201csecretly worked to destroy\u201d records related to a housing development after allegedly lying about its payments to subcontractors \u2014 by stuffing records in garbage bags, throwing them in a dumpster, and then removing the dumpster from the premises. (Rise and Grossmann vigorously denied these allegations and said the records were preserved digitally; a judge has not yet ruled on the claims.)<\/p>\n

Within a year, Rise Construction saw a flurry of other lawsuits, including two from banks related to $25 million and $10 million loans that had gone unpaid. Most of these suits, including the two filed by banks, are still pending. The company was in \u201cperilous financial condition,\u201d one bank told a judge in court. <\/p>\n

Amid his financial distress, Grossmann had also apparently failed to keep promises closer to home. In September 2023, his brother\u2019s elderly father-in-law sued him over a slate of allegations including misrepresentation and unjust enrichment. The father-in-law had sold Grossmann his family home, under the impression that Grossmann would develop it into condos and give him a cut of the profits \u2014 but the money never arrived. <\/p>\n

In the father-in-law\u2019s lawsuit, he accused Grossmann \u2014 who was building a new $2 million home during this period \u2014 of potentially \u201cmisappropriating\u201d the funds and using them to build his own home. The dispute is ongoing.<\/p>\n

As Grossmann told it, Rise was caught up in the commercial real estate bust in Boston after the Fed raised interest rates in the fall of 2022. But by the summer of 2025, as lawsuits piled up, it was clear that interest rates were far from the company\u2019s biggest concern. <\/p>\n

It was around this time that a new company was anonymously incorporated in Wyoming, using Grossmann\u2019s personal address, and registered to do business with the federal government. It was called Rudiarius \u2014 the name for a Roman gladiator who had earned his freedom.<\/p>\n

The Wild West of Warehouse Deals<\/strong><\/h2>\n

The Trump administration\u2019s massive deportation spending spree, which kicked off with a $75 billion handout to ICE in last summer\u2019s One Big Beautiful Bill Act, has proved a singular opportunity for enterprising government contractors hoping to strike gold.<\/p>\n

But some traditional actors appear to have been reluctant to get overly involved with ICE\u2019s more unorthodox plans. That includes Noem\u2019s initiative to convert giant distribution centers, built for companies like Amazon, into massive holding facilities for ICE detainees. Even ICE\u2019s private prison contractors, which have their own history of alleged abuses at their facilities, balked at this proposal.<\/p>\n

Read more Swing District Voters Want Major Change. That Could Help Democratic Socialists.<\/a><\/p>\n

\u201cI\u2019m sure a lot of what you might call reputable firms or large, well-known household brands don\u2019t want to touch this stuff with a 10-foot pole,\u201d said Joshua Harris, an economist and the academic director of the Fordham Real Estate Institute, noting that companies might worry about their public image or changing political headwinds down the line.<\/p>\n

To carry out the plans, ICE instead turned to new, untested, and more risk-tolerant firms. The Department of Homeland Security\u2019s reliance on little-known contractors \u2014 some with personal ties to the White House \u2014 has drawn accusations of cronyism and corruption at the agency.<\/p>\n

The first rumors around the warehouse program surfaced last fall. By January, the agency was starting to close deals on the facilities, and it awarded a sole-source contract to a brand-new firm incorporated in Puerto Rico, SK2 LLC, to help ICE acquire the facilities. <\/p>\n

Bloomberg <\/em>identified two business partners behind the new venture. One was Steven Kelley, a longtime defense contractor who, Bloomberg <\/em>reported, left the commercial real estate services firm CBRE to work on the warehouse project with ICE. The other, Scott King, also had a government contracting background.<\/p>\n

Kelley had originally proposed that CBRE \u2014 one of the largest commercial real estate firms in the world \u2014 work with the Department of Homeland Security on the project. But CBRE\u2019s leadership declined, and Kelley struck out on his own. Months later, SK2, Kelley\u2019s new firm, won a $6 million federal contract to secure the warehouse deals.<\/p>\n

As SK2 began to work on the warehouse purchases, which were drawing mounting public opposition, it struggled to find willing business partners. Originally, the contractor was working in partnership with a tribe in Kansas, the Prairie Band Potawatomi Nation, on the initiative. But after facing public pressure, the tribe pulled out of the deal.<\/p>\n

As the spring went on, local Boston news outlet the Boston Contrarian <\/em>reported that SK2 was offering attorneys at a prominent Boston law firm \u201ceye-popping\u201d sums of money to work on its ICE warehouse deals. The law firm, which the outlet didn\u2019t name, reportedly declined, fearing reputational damage.<\/p>\n

It was around this time that Grossmann\u2019s name began to surface in relation to ICE warehouse purchases. His signature appeared on a January memo that the Department of Homeland Security sent to the city of Social Circle, Georgia, about a warehouse the agency had purchased in the city. In the document, Grossmann signed off on claims that converting the 1 million-square-foot industrial warehouse into an ICE holding facility would have \u201cno adverse effect on the community.\u201d<\/p>\n

In April, amidst the still-ongoing court battle over ICE\u2019s purchase of a warehouse in New Jersey, improperly redacted documents first reported by Project Salt Box <\/em>revealed that Rudiarius, the new Wyoming firm associated with Grossmann, had commissioned the environmental assessment of the warehouse.<\/p>\n

Although Grossmann\u2019s name wasn\u2019t on Rudiarius\u2019 July 2025 filing documents, the original company address was a $2 million home in Dorchester, Massachusetts. Court documents obtained by The Lever <\/em>show that this address is Grossmann\u2019s personal residence.<\/p>\n

The warehouse purchases were put on pause after Noem\u2019s departure, and there were some indications that the agency planned to sell off the properties. But so far, ICE still owns the warehouses, as an internal feud rages over their future.<\/p>\n

At the same time, ICE has moved forward with the other prong of its new detention model: Buying private prisons that are already in operation. To close these deals, ICE has turned to the same real estate moguls that it used to buy up warehouses \u2014 including Grossmann.<\/p>\n

His name appears on the $1.5 billion purchase agreement between the Department of Homeland Security and CoreCivic, which the private prison giant disclosed to its investors in July. This time, Grossmann\u2019s name was not associated with the Wyoming firm incorporated with his address but a different company: SK2.<\/p>\n

Operation Bailout<\/strong><\/h2>\n

To Em Knepp, a researcher with Project Salt Box <\/em>with experience in government contracting, Grossmann\u2019s story \u201cfollows the trend of the current administration, or [the Department of Homeland Security] specifically in this case, bailing out people who are in financial trouble \u2014 whether it\u2019s Grossmann, here, or the various companies who owned failing warehouse assets.\u201d<\/p>\n

The layers of shell companies involved obscure how much money, exactly, Grossmann and other players are making from ICE\u2019s billion-dollar real estate deals. The Department of Homeland Security upped SK2\u2019s initial $6 million contract in June by $300,000; it is now set to end in September. It\u2019s unclear, though, how the funds are being divided among SK2\u2019s partners, or if there are subcontractors involved. <\/p>\n

The scope of SK2\u2019s role is also somewhat unclear. Based on the documents released by CoreCivic, which named Grossmann and SK2, Harris, of the Fordham Real Estate Institute, told The Lever <\/em>he believed the company was likely acting as an \u201cacquisition and due diligence agent\u201d acting on behalf of the Department of Homeland Security to secure the deal.<\/p>\n

There are likely even bigger deals to come. Initial planning documents for ICE\u2019s purchases of its own prisons included 10 facilities, according to records seen by the Washington Post<\/em>. The two CoreCivic facilities in California included in the document were sold to the Department of Homeland Security this month.<\/p>\n

But so far, GEO Group, another major private prison company, has not sold ICE any of the at least six facilities that the Department of Homeland Security has expressed interest in \u2014 although the company\u2019s CEO told investors in May that the company was discussing potential sales with ICE. Those prisons could include facilities in California as well as in Tacoma, Washington, and Aurora, Colorado.<\/p>\n

It might not be a coincidence that ICE has focused on buying up detention centers in more liberal states, where they have been subject to more aggressive state oversight and lawsuits over labor violations. In Washington state, lawmakers have been trying to force GEO Group to allow state officials access to the Tacoma facility to conduct health and safety inspections. But if the facility were federally owned, it could shield the prison from such local oversight, experts told The Lever<\/em> in March.<\/p>\n

These deals offer significant windfalls for the brokers working to close them. In addition to SK2, the real estate giant CBRE, which had declined a more public-facing role in the deals, was still willing to facilitate the CoreCivic prison transaction, according to the purchasing agreement, likely entitling it to a commission in the sale.<\/p>\n

CBRE, which also represented property owners of multiple commercial warehouses that were considered by ICE, did not respond to The Lever<\/em>\u2019s request for comment.<\/p>\n

In recent weeks, ICE has adopted a new strategy that could also prove a boon for the commercial real estate sector. As Project Salt Box <\/em>reported this month, the agency has been advertising new construction opportunities for contractors to expand its current facilities and build entirely new ones, rather than simply purchasing existing prisons or retrofitting warehouses. The maximum value of the new contracting vehicle, over several years, is $10 billion.<\/p>\n

In an interview with the Boston Contrarian<\/em> earlier this year, Grossmann elided any mention of his new side hustle. He told the outlet in March that he was focused on finishing Rise\u2019s remaining projects. The company was now operating with less than a quarter of the staff it once employed, and not accepting any new work.<\/p>\n

Read more Democrats Call for an Ethics Investigation Into GOP Rep. Max Miller<\/a><\/p>\n

\u201cIt has been a really rough ride, it really has,\u201d Grossmann said.<\/p>\n<\/p>\n<\/div>\n","protected":false},"excerpt":{"rendered":"

Opaque contracts and enormous windfalls are buttressing the buildout of ICE jails and their shadowy operators.<\/p>\n","protected":false},"author":1,"featured_media":1262,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[1],"tags":[],"class_list":["post-1263","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-interesting"],"yoast_head":"\nThis Developer Went From Financial Peril to Billion-Dollar Deals for DHS - Smart Moving Home<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/smartmovinghome.com\/?p=1263\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"This Developer Went From Financial Peril to Billion-Dollar Deals for DHS - Smart Moving Home\" \/>\n<meta property=\"og:description\" content=\"Opaque contracts and enormous windfalls are buttressing the buildout of ICE jails and their shadowy operators.\" \/>\n<meta property=\"og:url\" content=\"https:\/\/smartmovinghome.com\/?p=1263\" \/>\n<meta property=\"og:site_name\" content=\"Smart Moving Home\" \/>\n<meta property=\"article:published_time\" content=\"2026-07-31T20:10:55+00:00\" \/>\n<meta name=\"author\" content=\"admin\" \/>\n<meta name=\"twitter:card\" content=\"summary_large_image\" \/>\n<meta name=\"twitter:label1\" content=\"Written by\" \/>\n\t<meta name=\"twitter:data1\" content=\"admin\" \/>\n\t<meta name=\"twitter:label2\" content=\"Est. reading time\" \/>\n\t<meta name=\"twitter:data2\" content=\"12 minutes\" \/>\n<script type=\"application\/ld+json\" class=\"yoast-schema-graph\">{\"@context\":\"https:\\\/\\\/schema.org\",\"@graph\":[{\"@type\":\"Article\",\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263#article\",\"isPartOf\":{\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263\"},\"author\":{\"name\":\"admin\",\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/#\\\/schema\\\/person\\\/ec0d70042821fd684a174c8d0e8becfa\"},\"headline\":\"This Developer Went From Financial Peril to Billion-Dollar Deals for DHS\",\"datePublished\":\"2026-07-31T20:10:55+00:00\",\"mainEntityOfPage\":{\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263\"},\"wordCount\":2471,\"commentCount\":0,\"image\":{\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263#primaryimage\"},\"thumbnailUrl\":\"https:\\\/\\\/smartmovinghome.com\\\/wp-content\\\/uploads\\\/2026\\\/07\\\/8cd9ffdf3c7152267bcef5384cef2191.jpg\",\"articleSection\":[\"Interesting\"],\"inLanguage\":\"en-US\",\"potentialAction\":[{\"@type\":\"CommentAction\",\"name\":\"Comment\",\"target\":[\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263#respond\"]}]},{\"@type\":\"WebPage\",\"@id\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263\",\"url\":\"https:\\\/\\\/smartmovinghome.com\\\/?p=1263\",\"name\":\"This Developer Went From Financial Peril to Billion-Dollar Deals for DHS - 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