When the order of the Garter was founded, he was initiated as one of its first members and his stall in St. George's Chapel, Windsor was the eleventh on the side of Edward, the Black Prince.

When hostilities were renewed between England and France in 1354 Sir James was in constant attendance upon the Black Prince, and earned a great reputation for valour.

After the victory, the prince inquired after Sir James, who was brought to the royal tent, where Edward told him he had been the bravest knight on his side, and granted him an annuity of five hundred marks.

[2] A variation of this story states that, after commending highly his four esquires, and attributing his success mainly to their enterprising spirit, made over to them the donation of five hundred marks.

This act of generosity coming to the ear of the prince Edward, and, approving what he had done, confirmed the grant to the esquires, assigning to sir James an annual rent of six hundred marks.