The day after Larry Hogan became Maryland’s 62nd governor in 2015, the executive director of the Maryland State Ethics Commission, Michael Lord, sent him a letter. Hogan was coming to the top job not just as a politician but as president and principal owner of HOGAN, a multi-purpose real estate brokerage firm based in Annapolis. Lord was writing to tell Hogan that, as governor, he “should not personally participate in any matter that may come before a state agency that involves his business.” To be completely clear, Lord added that “participation includes supervision of others involved in a matter.”

That put Hogan in a spot. By its own account, HOGAN represented a “who’s who” of the Maryland real estate industry. As governor, Hogan’s powers would range from setting rules for housing projects to awarding grants and tax credits to developers. So Hogan entered into a trust agreement that he said would prevent conflicts of interest. But it was not a blind trust. He put his brother Timothy in charge of the firm and made several executives at the firm trustees. In a letter to Lord, Hogan wrote that the agreement would allow him to remain apprised of his firm’s investments, investors, and other matters including the location of its real estate projects. In April 2016, 15 months after Hogan took office, the State Ethics Commission approved the arrangement.

If Hogan hoped that the agreement would prevent the appearance of a conflict of interest, it didn’t. Over Hogan’s eight years in office, nearly 40% of the competitive affordable housing awards overseen by the governor went to developers listed as clients on HOGAN’s website, according to a TIME review of public records. Those awards were concentrated among six developers who competed against more than 60 other companies during that time. As one of three members of the Board of Public Works, an administrative body that determines how taxpayer money gets spent, Hogan voted on five occasions to issue additional loans or grants to four of those same developers, according to public records. All the while, Hogan continued to hold regular meetings with his company’s leaders, according to his official meeting calendar, which was obtained by the Washington Monthly via a FOIA request in 2019. "It's definitely a serious conflict of interest," says Richard Painter, chief White House ethics lawyer in the George W. Bush Administration. "He should have stayed away from it."

Maryland law prohibits government officials from taking part in decisions in which they or a close relative have a known financial interest, or if the decision could reasonably be expected to “result in a conflict between the private interest and the official State duties of the official.” A Hogan aide says he did nothing wrong. “Gov. Hogan adhered to a legally-binding Trust Agreement, approved by the independent State Ethics Commission, that prohibited his participation in any matters related to his business,” says Michael Ricci, a former state official and Hogan spokesman. Ricci says HOGAN had no involvement in the projects that went before the BPW.  

The exact nature of the developers’ relationships with HOGAN and the governor remains opaque. For nearly a decade, the six firms appeared on a list of HOGAN’s “longstanding” clients. Contacted by TIME, the developers’ responses ranged from descriptions of extensive collaboration over many years to denial they had been paying clients to a refusal to comment at all. Hogan declined to provide a detailed description of his relationship with those developers, nor did he answer questions about whether and how much he or his company made from listed clients with business before the state during his tenure.

HOGAN is a privately held company, and the former governor declined to provide TIME with his tax returns for all of his eight years as Maryland's chief executive. When running for reelection in 2018, he revealed making $2.4 million during his first three years in office from undisclosed sources, making him the first governor in Maryland history to make millions of dollars while in office, according to historians of the state. Hogan’s official annual salary ranged from $165,000 to $180,000. On a recent financial disclosure form he reported a net worth between $12.3 and $35 million.

Now the 68-year-old Republican is in a tight race for the U.S. Senate in this November’s election against Prince George’s County Executive Angela Alsobrooks. On the campaign trail, he has boasted that he “tripled the amount of affordable housing” as governor. During his tenure, however, Hogan didn’t disclose to at least one other BPW board member his relationship to the developers via his brokerage firm: “It wouldn’t occur to me,” says one, then Maryland Treasurer Nancy Kopp. “In all my years in politics, there have been times when people have recused themselves because there was a conflict.” TIME could find no record of Hogan recusing himself from an official government decision. When asked whether he ever had, Ricci did not provide examples of recusal and said that Hogan “did not participate in decisions he was not legally permitted to participate in.”

Legal and ethics experts say Hogan’s role overseeing and approving competitive affordable housing awards while his firm’s listed clients competed for public funds he controlled requires further scrutiny. “It’s wrong on its face,” says Danielle Brian, executive director of the Project on Government Oversight. “There is a law that appears to prevent this from happening.” Says Douglas Colbert, a University of Maryland law professor: “There's an absolute need for a full investigation, and the report should be made public."

Hogan began presiding over his administration’s first round of competitive affordable housing awards even while his trust agreement was still being drafted. In Maryland, the Department of Housing and Community Development periodically holds application rounds for developers seeking tax credits, grants and waivers to build and improve income-restricted housing. After an internal committee reviews the applications based on a points-based scoring process, the agency’s Secretary makes recommendations for final approval by the governor. “Ultimately the governor can say, Yay or Nay,” says a senior DHCD official who worked in the Hogan Administration and was granted anonymity because they were not authorized to speak publicly on the matter. “The governor is responsible.”

In previous rounds of competitive affordable housing project awards under Hogan’s predecessor in 2011 and 2012, HOGAN’s listed companies won 0% and 30% of the awards respectively, according to the award announcements, which are made public. When Hogan’s first awards were announced in January 2016, HOGAN’s listed clients won 47% of all state funds and Low-Income Housing Tax Credits (LIHTC), which are federal funds disbursed by the state, and an additional 27% of the waivers, which effectively greenlight the projects. For the rest of Hogan’s tenure, there were five more competitive funding rounds for affordable housing projects. Taken together, his company’s listed clients won between 25% and 43% of the tax credits and grants, and between 33% and 53% of the waivers in each round. The fall 2020 round broke Maryland state records, awarding nearly $40 million in state funds and federal tax credits to 18 projects out of 51 applications. HOGAN’s listed clients made up seven of them.

Oversight of the competitive housing awards wasn’t Hogan’s only involvement in running housing policy. The governor personally voted on grants or loans to several of the same HOGAN-listed developers from his seat on the three-member Board of Public Works. From 2016 to 2017, he approved between $600,000 and $1.8 million in loans and grants to four different companies that were listed as clients of HOGAN: Pennrose Properties, Homes for America, Osprey Property Company and PIRHL. The votes authorized or funded improvements or new construction for scores of affordable housing units across the state. Says former Democratic Maryland Governor Parris Glendening: “This is clearly something that should be explained to the public.”

HOGAN competitors and Maryland officials say that Hogan’s role in steering the state’s affordable housing may have drawn developers to work with his private firm. “The state has a large role to play in this because they actually allocate the credits. Hogan, as governor, was in charge of that,” says Bart Harvey, a former affordable housing developer in Maryland and former director of Fannie Mae. “Developers, knowing that, may on their own go to his entity because they think they get a step up in the very competitive tax credit allocation process.” The senior DHCD official who worked in the Hogan Administration expressed the same concern. “Based on my experience, developers will do anything to get a competitive advantage to win a deal,” the official says. “They will hire the right lobbyist. They will hire the right team. They will go where you tell them in order to win.”

All the developers that received affordable housing awards through the Hogan Administration met the scoring criteria and regulatory requirements for their projects. There is no evidence of any of them acting improperly. Hogan’s five BPW votes for his firms listed clients represent a small fraction of the state funds the BPW awarded to developers and contractors over Hogan’s eight-year tenure. Local officials say even the appearance of a conflict of interest is a problem. "Even voting for one, if it potentially benefits you financially, even after your tenure, is not something you do as a public official," says the DHCD official.

The DHCD awards and BPW votes are not Hogan’s first brush with potential conflicts of interest as governor. After the Washington Monthly reported in January 2020 on Hogan advancing transportation infrastructure near properties his real-estate firm owned, there was increased scrutiny on the governor, particularly his approval of a $58 million interchange in Brandywine, Md., a stone’s throw away from one of his properties, and $23.5 million in road improvements in Hyattsville, Md. A Maryland lawmaker proposed new ethics legislation and the government watchdog group Public Citizen filed an ethics complaint in February 2020. Shortly thereafter, HOGAN scrubbed from its website its entire client list, which included the names of the six developers that won awards during Hogan’s governorship. (TIME obtained the client list via the Internet Wayback Machine, a publicly available archive of Internet web pages.) A year later, the Maryland General Assembly unanimously passed the ethics bill, which enhanced disclosure requirements for public officials. Hogan quietly let the bill become law without his signature, but it went into effect after he left the governor’s mansion. In his Senate financial disclosure, filed to the Federal Election Commission, he reported making between $100,001 to $1 million on unimproved real estate in Brandywine and between $500,001 to $1,000,000 on unimproved real estate in Hyattsville.

The nature and extent of the relationship between the six developers and HOGAN remains unclear. Two of the developers, Osprey and PIRHL, declined repeated requests for interviews for this story. Conifer, which won ten of the awards throughout Hogan’s eight-year tenure, acknowledged its business relationship with HOGAN. “We have worked with Hogan Companies, among other land brokerage firms, to assist in locating vacant land for development,” the firm wrote in a statement. “Our selection of brokerage partners is based on project needs, market expertise, and availability, and Hogan Companies is one of several firms we have used over the years. Our experienced development team adheres strictly to and completes all regulatory processes for project approvals.”

Homes for America would not comment on its relationship with HOGAN, other than saying it has had new leadership since 2020 and has “no record” of paying the firm or of closing a transaction with them. Pennrose maintained a longstanding relationship with HOGAN. When asked for comment, a spokesperson said “Pennrose is not and has never been a client of Hogan.” Reached by phone on Oct. 2, Pennrose’s CEO Mark Dambly said, “I don’t know anything about anything.”

An executive with one of the companies agreed to speak on background with TIME and described a variety of services that HOGAN provided their company during the period Hogan was governor, including due diligence on potential sites for purchase, letters of intent to purchase properties, and consulting services. “We retained them, but we did not pay them because they would get paid at the sale of the property, which never happened,” the executive says. The executive adds that anyone engaged in the affordable housing business would need to get support from authorities to make a project economically feasible. “If you want to build new housing, and you want to serve people at lower income and keep rents affordable, then there has to be some subsidy available,” the executive says.

As governor, Hogan kept a close relationship with his trustees and his brother, whom he put in charge of the company. He had at least eight meetings with them between 2015 and 2018, his first three years in office, according to his meeting calendar. Ricci, the Hogan aide, denies Hogan received detailed information about his company’s business. “He received no briefings or updates on the company or its projects—only information regarding the trust itself for the purposes of financial reporting,” Ricci said in a statement.

Simultaneously controlling public housing funds as governor and maintaining an ownership stake in his private brokerage firm with potential knowledge of its business interests raises red flags for experts in government ethics and Maryland law, who say that Hogan’s situation was anomalous. Don Fox, former general counsel for the U.S. Office of Government Ethics in the George W. Bush and Barack Obama Administrations, says that Hogan approving awards to any of his firm’s clients, past or present, is cause for concern. Hogan should have disclosed his firm’s relationship with the developers, he says, and if that disclosure revealed an actual or apparent conflict, then he “should have recused himself, or let somebody else act on it.” Hogan’s trust agreement and approving of awards to his firm’s listed clients, he adds, is unlike anything he has ever seen. “That would just never fly under the federal system.”

Lord, of the Maryland State Ethics Commission, retired in May 2020, and couldn’t be reached for comment. His successor, Jennifer Allgair, cited Maryland law and longstanding Ethics Commission policy in declining to “provide any comment on, or confirmation of, any advice request, complaint or investigation matter.”

Hogan’s most immediate vulnerability is political. Ethics are already an issue in this election, and Hogan has attacked Alsobrooks for improperly claiming tax credits on a D.C. property she owns. (Alsobrooks says it was a mistake she was unaware of and that she will pay her back taxes.). Hogan’s own issues have come up through the ethics complaints filed against him as governor. Most recent polls show Alsobrooks gaining the lead. One poll, commissioned by AARP in August, had Hogan virtually tied with Alsobrooks, raising the prospect of a surprising upset for Republicans in a blue state that could tip the balance of power in Washington.

If Hogan wins, he would have some sway over housing policy in the state, including by advocating for funding levels, earmarks, and competitive funding awards for Maryland affordable housing organizations through the Department of Housing and Urban Development. When TIME asked whether Hogan would recuse himself from any Senate decisions that could potentially benefit his real estate business, Ricci said the ex-Governor would “follow the standing rules of the Senate, in these and in all matters.”

For now, HOGAN’s website remains clear about the advantages of doing business with the company: "If you want to determine the best strategy for taking your property through the governmental entitlement process as well as achieve the best development potential and highest return on your investment,” it says, “you only need to turn to HOGAN."