He was one of the most important noblemen below peerage rank[citation needed] in Devon in the last two decades of the 14th century.
[citation needed] He began as a combat squire and served in this capacity for many years probably originally lacking sufficient wealth to be considered a knight.
[1] After a lengthy military career Chudleigh had built up prestige, land, and power and was appointed Sheriff of Devon in 1376 as his father had served in 1335.
[1] Although Chudleigh derived much of his power from the Earls of Devon, he became an important royal servant and these two loyalties sometimes clashed.
[1] Chudleigh was often employed by the King to enforce royal authority in Devon, for example arbitrating Courtenay's land disputes.