Maxine Cheshire (born April 5, 1930) is an American former newspaper reporter who was best known for her work at The Washington Post between 1965 and 1981.
Maxine Hall was born in Harlan, Kentucky, on April 5, 1930. She studied at the University of Kentucky between 1949 and 1950, and for a further two years at Union College.
She first worked as a reporter for two local papers, the Barbourville Mountain Advocate and The Harlan Daily Enterprise. From 1951, she worked for three years for the Knoxville News Sentinel as a police reporter. In 1954, she joined The Washington Post. She first worked as a society reporter until 1965, when she began to write her own column, entitled "VIP", until 1981. In that guise she did not simply stick to the contents of a typical gossip columnist, but spoke of other, more serious matters such as bribes to government officials. Because of this, she was known and feared by the establishment, having worked on a variety of scandal-type stories concerning various political leaders, such as Koreagate, the lechery of John F. Kennedy, and Richard Nixon's habit of keeping, illegally, gifts given to him by foreign dignitaries. This line of work earned her the nickname "The Last of the Fast-Draw Gunslingers" at the Post.
She was the subject of one of Frank Sinatra's most widely known slurs in 1973 when, at a pre-inaugural party, he told her, "Get away from me, you scum. Go home and take a bath... You're nothing but a two-dollar cunt. You know what that means, don't you? You've been laying down for two dollars all your life". With that, he thrust two one-dollar bills into her wine glass in front of a variety of witnesses and added, "Here's two dollars, baby, that's what you're used to".