Like many members of the Welsh gentry, Herbert was a notable bardic patron. He was the principal patron of Ieuan Deulwyn, and was also a patron of Guto'r Glyn as well as others. He hosted a bardic debate at Coldbrook House between Deulwyn and Bedo Brwynllys. He was eulogized by Ieuan Deulwyn, Bedo Brwynllys, Hywel Dafi, and (jointly with his brother William) Huw Cae Llwyd.[3]
Like his brother, he was a supporter of the House of York during the Wars of the Roses. He fought alongside his brother at the Battle of Edgcote (a victory for rebels who supported the Earl of Warwick and the Duke of Clarence), where he was captured and executed. He is interred with his wife at Abergavenny Priory, near other members of his family.[4]
1 Briefly joined the Lancastrians. 2 Briefly joined the Yorkists. 3 Defected from the Yorkist to the Lancastrian cause. 4 Initially a Yorkist who later supported the Tudor claim. 5 Initially a Lancastrian who later supported the Tudor claim.