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How Well Do Adam Cloud and Earl O'Garro Know Each Other?

Fortnight Journal
Credit City of Hartford
City of Hartford
Hartford city treasurer Adam Cloud.

In our continuing coverage of the missing $670,000 in Hartford insurance premiums, there are at least two main players: city treasurer Adam Cloud, and Earl O'Garro, the CEO of Hybrid Insurance Group. Lots of questions remain unanswered. One is this: What kind of history do the two men have?

"Displaying moral integrity in the face of apparent defeat is rare," Adam Cloud wrote of Earl O'Garro in a 2012 email.

So far, there are a few answers. One is that O'Garro rents office space from Cloud and his family. Another is that O'Garro hired Cloud's brother to be his lobbyist. But there's a lot more. Emails obtained from Hartford City Hall show that Cloud introduced O'Garro to Mayor Pedro Segarra at a downtown restaurant in 2011. O'Garro called Cloud "a mutual friend."

Other emails show that in June 2012, O'Garro set up a dinner with "conversationers." It's unclear where or with whom. Another email shows that both men's names appeared on a receipt for a hotel room in New York City over a year ago.

Perhaps most telling: Cloud wrote O'Garro a glowing letter of recommendation in May 2012. "The tenacity, knowledge, and expertise that Hybrid Insurance Group brings to the table is unmatched," Cloud wrote. "The fact that Mr. O'Garro and his team have moral compasses that are positioned on thinking what is best for the insured is first reason enough. Displaying moral integrity in the face of apparent defeat is rare. Fortunately for the City of Hartford their integrity made all the difference."

O'Garro was supposed to pay $670,000 in insurance premiums on the city's behalf. Cloud -- the city's treasurer -- wired him the money to do so. But O'Garro never paid. Since then, officials at the city and the Hartford Public Schools have questioned whether Cloud steered business to a man with whom his family had a business interest. Cloud has long denied it, and said he's a victim of nasty politics.

Cloud has said that he in no way helped Hybrid get city business. For Wednesday's story, we sifted through city emails and found some that appeared to contradict that statement. It looks as if, at the very least, Cloud sent an email on the company's behalf. 

We also found an email and a hotel receipt for a stay at the W Hotel in New York City. The second page of the receipt said that O'Garro and Cloud were booked as guests in the same room in August 2012. In the email, Cloud also said O'Garro picked up the tab, which the receipt showed as $309.

It's unclear whether Cloud or O'Garro actually used the room. It's equally unclear why this apparently became a billing issue for the city six months later, the date on Cloud's email. Lastly, we don't know why they would have been in New York to begin with. 

We've asked Corey Brinson, O'Garro's attorney, for comment. In an email, Brinson said he doesn't represent O'Garro anymore.

For his part, Cloud considers the matter closed. "I am gratified that the Hartford Internal Audit Commission reported that after examining every angle of the financial transaction to Hybrid they found no fraud or criminal intent," Cloud wrote in an email. "Furthermore, they found there is no evidence that I financially gained from the transaction to Hybrid. I now consider this matter closed, and have moved on to refocus on my important duty as custodian and investor of all City funds."

Jeff Cohen started in newspapers in 2001 and joined Connecticut Public in 2010, where he worked as a reporter and fill-in host. In 2017, he was named news director. Then, in 2022, he became a senior enterprise reporter.

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