Robert Herle was associated with the Bassett family of Drayton in 1339 as retainer to the Bassett manors of Moulton, Buckby, Olney and Walsall.
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Robert was overlord at the Leicestershire village of Kirby Muxloe, but more significantly became one of Thomas, the earl of Warwick's most prominent retainers and was granted a life indenture at Wadborough.
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Warwick granted Herle the wardenship of Barnard Castle along with its forests and lands, this, it has been stated made Herle a pivotal figure in the running of the earl's estates.
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