(Bloomberg) -- Before the lawsuits started piling up in courtrooms across Connecticut, before his employer accused him of running a “massive Ponzi-like fraud,” and before the FBI showed up, Robert Cappelletti looked well on his way to pulling off one of the greatest muni-bond coups of all time.

The plan Cappelletti had put together was so audacious it bordered on the fantastical. The housing agency he ran in Groton, a sleepy town of some 40,000 people along Connecticut’s Thames River, would sell $750 million of bonds to jumpstart a $4 billion project to transform a bunch of run-down shopping plazas into a sprawling, up-scale development. There’d be a new train station, a hospital, almost 2,000 apartments and dozens of shops and restaurants. 

It would have been the biggest local bond issue in the state’s history and expanded the tiny Groton agency far beyond its role managing two apartment complexes. 

And yet Cappelletti — a part-time employee with a mixed record running other housing agencies in the state — breezed through a series of crucial steps needed to complete the sale. He got approval from the five-person board that runs the agency; crafted a brief financial projections statement; scored an investment-grade bond rating; and started the process of lining up buyers for the debt. 

It was only when the bond sale collapsed this winter and Cappelletti was removed from office that the complex financial web that he had spun across Connecticut for years came to light. Cappelletti engaged in double-dealing, created shell companies and failed to disclose loans he took out, leaving, in the process, a trail of financial wreckage across the state, lawyers for the Groton agency alleged in the most high-profile case against him.

In February, they sued Cappelletti for fraud, claiming he borrowed at least $3 million without the commission’s knowledge through subsidiaries he controlled. In subsequent court documents, the authority alleged Cappelletti also took “millions of dollars” from non-commercial lenders and other “questionable entities” that were then transferred to others, including businesses owned by his brother, David, that received about $1 million. The housing authority’s attorneys are working with the FBI, which is investigating, according to people familiar with the matter who asked not to be identified discussing internal matters. 

“Everybody is disgusted,” said Ric Silver, who lives in an apartment in Pequot Village, a 104-unit complex managed by the authority. 

Cappelletti declined to comment through his attorney, Joseph Martini, who also declined to comment. Cappelletti's brother, David, who was named as a co-defendant in the suit last month, also declined to comment. On June 2, in court papers filed in connection with the Groton case, Ivan Ladd-Smith, another lawyer for Cappelletti, said he intends to deny the allegations.  A press official for the FBI declined to comment. Robert Frink, the chair of the Groton Housing Authority, said the board has opened an investigation but is “unable to go into greater detail at this time.” 

That Cappelletti drew so little scrutiny as he pushed ahead with the deal is a testament to the vulnerabilities in the vast network of government agencies struggling to provide affordable housing to low-income families across America. To finance new projects and try to address the housing crisis, the local agencies routinely sell municipal bonds, a loosely regulated corner of the securities market where deals are often just rubber-stamped.

Many of the agencies have been plagued by mismanagement, poor oversight and corruption. Since 2023, prosecutors have brought bribery and fraud charges against housing authority officials in Ohio, North Carolina, Georgia, Pennsylvania, Illinois, Montana and New York, where 70 former and current New York City Housing Authority officials were ensnared in a historic case. In Connecticut, the events in Groton are drawing fresh scrutiny to the more than 100 independent housing agencies across the state, which only has enough affordable rental homes to meet the needs of about one-third of the lowest-income households.

“Until we fix the regulatory disconnect,” said Robert Boris, chair of Groton’s economic development commission, “bad actors will continue to exploit it and working families will continue to the pay the price.”  

Cappelletti, 58, has worked in public housing for two decades. A graduate of Assumption University, a Catholic school in Worcester, Massachusetts, he joined the housing authority in Stamford, Connecticut, in 2002 to run the city’s Section 8 voucher program, according to his LinkedIn profile. In 2009, he became the executive director for the Meriden Housing Authority and five years later tacked on a similar part-time job for the Waterbury Housing Authority.  

Just before starting at Groton in 2016, he left the post in Waterbury. There, an investigation found he had used $56,653 of public funds to buy a Chevrolet Silverado for business and personal use even though he wasn’t entitled to a vehicle, had slid someone onto the payroll without the agency’s approval and allowed a contractor to live rent-free in an apartment managed by the agency in exchange for painting work. Cappelletti and Waterbury reached a separation agreement that included no admission of wrongdoing.

The Groton job was a relatively modest one — mostly the oversight of 174 rental units — that Cappelletti could do while still running the agency in Meriden some 50 miles away. 

Cappelletti, though, envisioned much bigger things for Groton. A manufacturing hub just off the Long Island Sound, best known for its naval base, General Dynamics Corp.’s submarine factory and the sprawling research facility for the drugmaker Pfizer Inc., the town had a relatively strong economy. But that had left it with a shortage of affordable housing, and its main commercial corridor was lined with aging, strip-style retail. 

Cappelletti called his development project Groton 2030. It’d reserve 20% of the 1,925 apartments for lower-income residents, a key selling point to the authority’s board, which approved the project in June 2023. Per the plan, Cappelletti would oversee the project himself through a development arm of the housing authority instead of hiring an experienced developer or soliciting bids. 

One of the housing agency commissioners who signed off on the plan, Joe Greene, soon had regrets. In an interview, Greene said he had reluctantly approved the bond during a last-minute video call but had doubts after asking for details. Cappelletti never presented a real business plan, Greene said, and the town had not received formal notice that one of its agencies was planning a massive bond sale. 

At odds with the rest of the board, Greene resigned that September. Two years later, he remains mystified by it all. “I still don’t know how you’re going to pay off a $750 million bond in a five-year timespan when you don’t own the property and when there was no business plan,” he said. “People were amazed at the amount of money.”

With the approval in hand, Cappelletti put the deal in motion.

He had the Groton authority pay $25,000 to a New Jersey-based investment banker, according to a check register obtained under a freedom of information request. The authority also hired Connecticut law firm Pullman & Comley as bond counsel and obtained an ‘A’ rating from Egan-Jones based on a few financial projections it turned over.Pullman & Comley declined to comment. Eric Mandelbaum, general counsel for Egan-Jones, said the firm can't comment on particular transactions but “stands behind its work and record, which are based on methodologies that are publicly available.”

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The sale bogged down after that. Month after month, its completion kept getting delayed. Then, in May 2024, it all started to unravel on Cappelletti when the Groton commissioners received subpoenas ordering them to travel across the state to provide sworn testimony.

Months earlier, a lawsuit had been filed against Cappelletti’s Meriden Housing Authority and a subsidiary, Maynard Road Corp., that had defaulted on a $16 million loan. 

The lender, Titan Capital, subpoenaed the Groton commissioners because Cappelletti had made $629,000 of loan repayments with funds pulled from their agency, not Meriden’s. The Meriden agency is now on the hook for about $30 million — to repay the Titan loan with interest as well as $12.5 million owed to Citizens Bank for a project in Bristol, Connecticut.

Back in a September 2023 board meeting, the Groton commissioners had asked Capelletti about the cash used to pay off Titan, which was recorded as an expense for the Groton 2030 project. They were assured they’d be reimbursed when the bond deal closed, minutes of the meeting show.

But the Meriden lawsuit raised new questions, and when Groton commissioners started digging, they found that companies controlled by Cappelletti had bought properties in Winchester, Connecticut, and Fitchburg, Massachusetts to redevelop. Cappelletti also allegedly forged a resolution to approve $2.7 million of lease agreements for the authority, according to the February lawsuit filed by the Groton agency.

“This case involves the discovery of a massive Ponzi-like fraud,” lawyers for the agency said in a court filing. “Over the course of at least seven years, Cappelletti accepted millions of dollars in funds from non-commercial lenders or other questionable entities.” 

In January, the agency suspended Cappelletti and canceled his contract. The FBI probe continues and the lawsuits are wending their way through Connecticut courts. “Our focus now,” said Frink, the chair of the Groton Housing Authority, “is to ensure a complete and fulsome investigation.” 

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