Ware was an influential member of the "Mandarins of the Yellow Button" in Boston. The "Yellow Button" was a pin worn in the hats of Chinese imperial officials to indicate high rank in the civil service. The Boston Mandarins were a group of chess players in the late 19th century, including John Finan Barry, L. Dore, C. F. Burille, F. H. Harlow, Dr. Edward Mowry Harris, C. F. Howard, Major Otho Ernst Michaelis, General William Cushing Paine, Dr. H. Richardson, C. W. Snow, Henry Nathan Stone, Franklin Knowles Young, and Preston Ware. The group was the foundation of what would become the modern Deschapelles Chess Club in Boston.
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Ware was an avid tournament player and played in the Second International Chess Tournament, Vienna 1882, the finest chess tournament of its time. He finished in sixteenth place of eighteen scoring a total of 11 points out of 34, but he did beat Max Weiss and the winner of the tournament, Wilhelm Steinitz in a game lasting 113 moves. At the time, Steinitz had not lost or drawn a game for nine years prior to this tournament and was the unofficial World Champion. Ware also competed in the first, second, fourth and fifth American Chess Congresses.
Ware's other claim to fame was his eccentric opening play. He used the Ware Opening (then known as the Meadow Hay Opening), the Corn Stalk Defence (sometimes known as the Ware Defence), and the Stonewall Attack. Around 1888 he reintroduced the Stone-Ware Defence to the Evans Gambit, named also for Henry Nathan Stone (1823–1909). (It had originally been played by Alexander McDonnell against Bertrand-François Mahé de La Bourdonnais in 1843.)
- Gaige, Jeremy (1987), Chess Personalia, A Biobibliography, McFarland, p. 456, ISBN 0-7864-2353-6
- Brace, Edward R. (1977), An Illustrated Dictionary of Chess, Hamlyn Publishing Group, pp. 177, 302, ISBN 1-55521-394-4
- Second International Chess Tournament, Vienna 1882 at Chessbase.com
- Whyld, Ken (1986), Chess: The Records, Guinness Books, p. 38, ISBN 0-85112-455-0
- Ware's winning game against Steinitz at Chessgames.com
- Hooper, David; Whyld, Kenneth (1992), The Oxford Companion to Chess (2 ed.), Oxford University Press, p. 399, ISBN 0-19-280049-3