Garrison Keillor picked up the habit of wearing red socks from Sibley.
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Later on, Sibley moved with his mother to Fayetteville, North Carolina where he received his education and apprenticed as a bookkeeper in the counting house of John Winslow.
He was elected as a Whig to the 25th United States Congress, holding office from March 4, 1837, to March 3, 1839.