[2][3] Although many of his poems are addressed to pro-Lancastrian gentry, he was not above praising Yorkist patrons when occasion demanded it,[3] such as the Vaughan family of Hergest, Herefordshire, with whom his name is often associated.
There is a story, originating in a note on a manuscript copy of his poetry, that Lewys settled at Chester and was later ejected from the city by its burgesses for marrying a widow without their consent.
Other stories attached to different manuscripts claim that he was instead driven out of the staunchly Yorkist city for making a verse prophecy that Henry Tudor would become king.
He is known to have had at least one son, John, whose death at the age of 5 led Lewys to write one of his most powerful poems, the elegy Marwnad Siôn y Glyn, part of which runs, in a translation by the academic and poet Gwyn Williams, as:
[5] A tradition states that Lewys, who appears to have died around 1490, was buried at Abergwili, but his place of burial and exact date of death remain unconfirmed.