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Harleysville Worcester Insurance, the oldest insurance company based in Massachusetts, provides multiple lines of commercial property and casualty coverage in the northeastern US. A network of independent agents sell the company's products, which include workers' compensation and home-owned business policies. The firm writes insurance in Connecticut, Maine, Massachusetts, New Hampshire, New York, Rhode Island, and Vermont; it is also licensed in Michigan and Ohio. Worcester Insurance Company, established in 1823, was acquired by Harleysville Group in 1983; the present name was adopted in 2001.

HCC Insurance Holdings, Inc., together with its subsidiaries, provides property and casualty, surety, group life, accident, and health insurance coverage, as well as related agency and reinsurance brokerage services to commercial customers and individuals worldwide. It underwrites financial insurance risks in its financial products line of business, which includes directors’ and officers’ liability, employment practices liability, errors and omissions liability, surety and credit, and fidelity insurance products. The company writes medical stop-loss insurance that provides coverage to companies, associations, and public entities that elect to self-insure their employees’ medical coverage for losses. It also engages in insuring aviation risks, which include coverage for antique and vintage military aircrafts, cargo operators, commuter airlines, corporate aircrafts, fixed base operations, military and law enforcement aircrafts, private aircraft owners, and rotor wing aircrafts. The company offers hulls, engines, avionics and other systems, liabilities, and cargo and other ancillary coverage. Its London market account business consists of marine, energy, property, and accident and health businesses. In addition, HCC Insurance Holdings underwrites property and liability businesses, such as event cancellation, contingency, public entity, and U.K. liability; and writes facultative or individual account reinsurance, and treaty reinsurance businesses. The company markets its products directly to customers, as well as through a network of independent and affiliated brokers, producers, agents, and third party administrators. HCC Insurance Holdings was founded in 1974 and is headquartered in Houston, Texas.

Hilltop Holdings Inc., through its subsidiary, NLASCO, Inc., operates as property and casualty insurance company in the United States. The company’s personal line products include homeowners, dwelling fire, manufactured home, flood, and vacant policies. Its commercial line products comprise commercial, builders risk, builders risk renovation, sports liability, and inland marine policies. Hilltop Holdings Inc. distributes its insurance products through a network of independent agents and managing general agents. The company was formerly known as Affordable Residential Communities Inc. and changed its name to Hilltop Holdings Inc. in July 2007. Hilltop Holdings Inc. was founded in 1998 and is headquartered in Dallas, Texas.

Hiscox focuses on niche risks rarely placed by other insurers. The company also provides reinsurance and operates a Lloyd's of London syndicate. Products include personal accident, travel, and kidnapping coverage for high net-worth individuals and a variety of protection for businesses (small and medium-sized), including fine art, marine, liability, political risk, professional indemnity, and terrorism policies. Hiscox's biggest market is the US, where it has expanded its presence through acquisitions and new operations, including offering professional liability coverage to the technology, media, and telecommunications industries.

Hochheim (pronounced "Hoe Hime") Prairie Insurance provides property/casualty insurance to residents of rural Texas towns. Products include auto, homeowner, farmowner, small business, and machinery coverage, as well as insurance for hay, feed, seed, and fertilizer; water and irrigation systems; and windmills. The company sells its products through a network of some 200 independent agents across the state. Subsidiary Texana Financial provides non-insurance services. Hochheim Prairie Insurance was founded by a group of rural Texans in 1892 to help protect members from property losses due to storms and fires; it is mutually-owned by its 120,000 policyholders.

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