It’s been a difficult quarter for Hartford Financial Services Group. The company lost about $500 million in the past three months, due to the recent bear market and declining customer retirement accounts.

The company, which sells life insurance and property-casualty coverage, lost nearly $110 million in the Japan annuity business, according to a presentation given today in Hartford, Conn. $230 million was lost from retirement products; catastrophe claims drew another $130 million loss.

Since 2009, when Chief Executive Officer Liam McGee came on board, the company has taken steps to minimize exposure during down markets, including minimizing the sale of variable annuities. Hartford halted new sales in Japan that year, while maintaining existing exposure tied to annuities purchased before the financial crisis.

“While challenges exist, our risks are significantly reduced and manageable,” the company said in today’s presentation. 

The insurer dropped 36 cents, or 2.1 percent, at 9:39 a.m. in the New York Stock Exchange, the largest drop in the 24-company KBW Insurance Index. 

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