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James or Jim Caldwell may refer to:

Politics

James Caldwell (Ohio politician) (1770–1838), U.S. Representative from Ohio, son on James Caldwell (1724–1804), an Irish emigrant who founded Wheeling, West Virginia
James Caldwell (Missouri speaker) (1763–1840), first Speaker of the Missouri House of Representatives
Jim Caldwell (Arkansas politician) (born 1936), former member of the Arkansas State Senate
Buddy Caldwell (James David Caldwell, Jr., born 1946), American politician and attorney from Louisiana
James Caldwell (British politician) (1839–1925), Member of Parliament for Glasgow St. Rollox, 1886–1892, and Mid Lanarkshire, 1894–1910
James Eber Caldwell (born 1943), member of the Canadian House of Commons

James Caldwell (clergyman) (1734–1781), Presbyterian "soldier parson" in the American Revolutionary War
- SS James Caldwell, a Liberty ship
James Caldwell (Latter Day Saints), dissenting apostle from the Church of Jesus Christ (Bickertonite) who formed the Primitive Church of Jesus Christ
James Caldwell (died 1770), one of five American colonists killed in the Boston Massacre
James H. Caldwell (1793–1863), American actor and theatre manager
James Emmot Caldwell (1813–1881), American jeweler
James Erwin Caldwell (1854–1944), American businessman and banker from Tennessee
James F. Caldwell Jr. (born 1959), admiral in the United States Navy
James R. Caldwell (1778–1804), United States Navy officer
James Caldwell (mathematician) (born 1943), British mathematician
Sir James Caldwell, 1st Baronet (by 1634–c. 1717), of the Caldwell baronets
Sir James Caldwell, 4th Baronet (c. 1720–1784), Anglo-Irish soldier and author
Jim Caldwell, game show host who emceed Tic-Tac-Dough, 1985–1986, and Top Card, 1989–1993
James Alexander Malcolm Caldwell (1931–1978), British Marxist writer