Bartholomew Wingfield I is considered to be the first Wingfield. According to legend, he slayed a dragon that was terrorizing his village. He then drank its blood and gained its strength. He is still honored by the Wingfield family.

He is considered to be the pinnacle of Wingfields. As a result, it is heavily frowned upon for modern Wingfields to name children after him because it is believed that one cannot be better than he was. This has been disregarded, such as with Bartholomew Wingfield VI.