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At one time, Chesterfield was one of the three most smoked brands of cigarettes in the United States. The non-filtered version is known for being very strong.

Chesterfield was the Liggett & Myers Tobacco Company’s best known cigarette brand, which they made from 1911 until 1999. The brand was first introduced in 1873 by the Drummond Tobacco Company of St. Louis, Missouri, U.S.A.. James T. Drummond (1834-1897) was a successful plug tobacco manufacturer who had introduced Chesterfield, Cannon, and Drum cigarettes as a sideline. A 'plug tobacco war' was fought during 1897 and 1898 with Drummond and Liggett & Myers on one side battling James Duke and his American Tobacco Company monopoly. The two St. Louis manufacturers lost, and Duke bought Drummond's company in October, 1898. Liggett & Myers became part of Duke's trust the following year. American Tobacco continued to manufacturer Chesterfield until the 1911 trust dissolution. Chesterfield was one of the cigarette brands awarded to the Liggett & Myers Tobacco Company, and ironically, W. Duke Sons & Company became a subsidiary.

Liggett & Myers reblended and repackaged Chesterfield to compete with the successful 1913 introduction of R. J. Reynolds' Camel Cigarettes. Originally made as a 70 mm non-filtered cigarette, Chesterfield was the first brand in America to be extended when L. & M. brought out Chesterfield in a king-sized (85 mm) format in 1952. The filtered version was introduced in 1966, followed by Chesterfield 101s in 1967 (the latter being relaunched, along with Chesterfield 100s, in 1983). Chesterfield Lights were brought out in 1988.

The name of the Liggett & Myers Tobacco Company was changed to the Liggett Group in 1976. In 1978, Liggett sold the international rights of their brands to Philip Morris International. Twenty-one years later, Philip Morris U.S.A. (now Altria) purchased the American rights to Liggett's Chesterfield, L & M and Lark brands. Philip Morris still manufactures Chesterfield today as a discount brand.

The history of Chesterfield's manufacture in southern Africa is worthy of note: in 1981, Philip Morris International ended their operations in appartheid-era South Africa due to increased sanctions, not to return until 2003. The Chesterfield brand was licensed to British American Tobacco South Africa, who held the right to manufacture and sell Chesterfield in Africa south of the Congo and Malawi from 1981 until 2007, when it was reclaimed by Philip Morris S.A.. A news report of this can be found at Chesterfield Filter (American version) KS-30-H - South Africa.

The American-blend, plain-end version of Chesterfield was manufactured in Canada by Imperial Tobacco Canada, successors to Philip Morris & Co. Ltd. of Canada; it was sold until the early 1990s.

Chesterfield is sold in numerous countries, including Argentina, Austria, Belgium, Czechia, Finland, France, Germany, Greece, Holland, South Africa, Switzerland, Turkey, and the Ukraine.

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