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1.
well off, especially in terms of happiness or wealth(from the notion of a well developed high cotton crop that one would not need to bend over to pick, used in the Southern U.S. since the 1920)
He was in high cotton by the time he retired.
by The Return of Light Joker October 12, 2008
 
2.
recently come into very good circumstances
He's in high cotton now with the new job.
by Arlan Holt March 29, 2004
 
3.
To have a lot of money. Prominently featured in the country-western song "High Cotton" by Alabama
When we were kids, we thought we were in high cotton if we had a dollar.
by LB March 31, 2004