Background
He was the third son and heir of Aubrey Wittlebury (1306–1349) of Whissendine, Rutland, a member of one of the leading families of the county.
He was the third son and heir of Aubrey Wittlebury (1306–1349) of Whissendine, Rutland, a member of one of the leading families of the county.
He served on the bench as a Justice of the Peace for Rutland from 1368 to 1399 and was appointed High Sheriff of Rutland for 1372–1374 (2 years), 1377–1378, 1381–1382, 1388 and from 1399 to his death in 1400. He was elected knight of the shire (Member of Parliament) for Rutland 6 times between 1372 and 1395.