Six sources, five wives, and this does NOT include a rumored early Chickasaw wife
1. He settled at Fairfields, a plantation home on Great Contentnea Creek named for Fairfield, Connecticut, the birthplace of his 1st wife, Ann McCarty, whom he had married on 18 Oct. 1744. They had three daughters, Saranna (m. William McTyer), Elizabeth (m. John Cade), and Agnes (m. John Gibson). (1)= Dictionary of North Carolina Biography
2. Husband of Eleanor (Unknown) Adair — married [date unknown] [location unknown] Father of Joseph Adair Jr. and John Adair Sr (2)= WikiTree @ https://www.wikitree.com/wiki/Adair-114
3. Married to Indian Cheraw, Full Blood Cherokee Married 11 June 1734 to Anna McBride 1710- with -Edward Adair -John Adair 1753-1815 -James Adair 1757-(3)= Cecelia Kolene Hogue @ https://gw.geneanet.org/chogue?lang=en&n=adair&oc=0&p=james+robert (tertiary source)
4. Children of JAMES ADAIR and ESTER MCBRIDE are:
i. JOHN2 ADAIR, SR, b. 1753.
ii. EDWARD ADAIR, SR, b. 1755; d. August 1820.
(4)= Hicks, James R. “Cherokee Lineages: Register Report of James Robert Adair, Sr.” Genealogy.com
5. Generally tertiary sources are leads only but this guy has tons of research attached, see the overview. Family: Eleanor, b. Abt 1726, Chickasaw Nation, Indian Territory, United States , d. Aft 7 Jan 1803, of Duncan Creek, Laurens, South Carolina, United States (Age ~ 77 years) United States James married Eleanor of the Chickasaw Nation in about 1744. Eleanor was born in the Chickasaw Nation say about 1726. She was a member of the Panther clan. -James Adair, b. Abt 1748, Chickasaw Nation, Indian Territory, United States , d. 18 Aug 1818, Duncan Creek, Laurens, South Carolina, United States (Age ~ 70 years) -Joseph Adair, b. Abt 1750, Chickasaw Nation, Indian Territory, United States , d. Aft 5 Feb 1804, of, Laurens, South Carolina, United States (Age ~ 54 years) -Laferty Adair -John Adair, b. Abt 1754, Chickasaw Nation, Indian Territory, United States , d. From 4 Nov 1815 to 4 Dec 1815, of, Oconee, South Carolina, United States (Age ~ 61 years) -Edward Adair, b. Abt 1756, Chickasaw Nation, Indian Territory, United States , d. Aft 3 Nov 1800, of, Oconee, South Carolina, United States (Age ~ 44 years) -Hannah Adair, b. Bef 1759, of Duncan Creek, Laurens, South Carolina, United States , d. Aft 1810, of Duncan Creek, Laurens, South Carolina, United States (Age > 53 years) - NN Adair, d. Aft 1791, of, , Georgia,@ https://myfamilysearch.net/getperson.php?personID=I3679&tree=2005217a
6. According to Emmet Starr, "____ Adair (had sons) John Adair m. Jennie Kilgore (and) Edward Adair m. Elizabeth Martin."
Reading subsequent research #5 suggests that both James Adair Sr and James Adair Jr had wives named Eleanor