Complex sentence: He appears to have enjoyed royal favour as early as 1399, being described as a "retainer for life" of the English Crown and was granted an annuity from the customs of Drogheda.
Split into simpler sentences: He appears to have enjoyed royal favour as early as 1399, being described as a "retainer for life" of the English Crown. He was granted an annuity from the customs of Drogheda.