Lee’s background, like that of his probable kinsman, Thomas Lee I, is obscure. If he was the William Lee said to be ‘insufficiently qualified’ to be a coroner of Shropshire but nevertheless re-elected to that post three times between 1381 and 1390, then he lived at Wilderhope, at least at the beginning of his career. Lee only emerges from obscurity on his marriage to Joan Peshale, which brought him an interest in substantial estates, but also put to the test his ability as a lawyer in the extensive litigation arising from Joan’s contested inheritance. When Sir William Shareshull, grandson of the chief justice of the same name, died in 1400, his heirs were the descendants of his sister Elizabeth: her daughter Katherine, wife of Roger Willey, and her grand daughters, Joan Lee and Isabel and Joyce Harcourt. In the first of many lawsuits over the division of the estates, in 1401, Richard Harcourt, father of Isabel and Joyce, made good his claim to the Staffordshire manors of Shareshull, Great Saredon, Little Saredon and Lache, which with two parts of the manors of Coven and Brinsford were settled on his sole surviving daughter, Isabel, five years later. By 1411 Patshull was in Roger Willey’s possession for life, although he paid £4 5s.8d. a year to the Lees, to whom it was to revert after his death. The Lees did acquire Boninghall (Shropshire), Rousham, Barton ‘Odonis’ and Dernford (Oxfordshire), and late in life Joan also took possession of Shareshull itself, although not without considerable difficulty. Other lawsuits were concerned with her claims to property in Somerset.
Lee often appeared as a mainpernor in Chancery and at the Exchequer for other Salopians such as Richard Chelmswick and Sir John Cornwall. In November 1397, a few months after his only known Parliament, he stood surety for Sir Edward Charlton (afterwards Lord Charlton of Powis), undertaking in the sum of 500 marks that Sir Edward would appear before the King’s Council. From 1400 onwards he was sometimes asked for legal advice by the burgesses of Shrewsbury, receiving in return a fee of 20s. a year and occasional gifts of wine, while one of the most prominent of their number, Thomas Skinner, made him an executor of his will.
Before the end of Henry V’s reign Lee had risen to be an apprentice-at-law, and it was no doubt because of his profession that he was appointed to many royal commissions of a judicial nature. Under the Lancastrians he served as an escheator, not only in Shropshire but also in Staffordshire (where his wife’s manor of Knightley was situated). In 1420, during the latter escheatorship, he was appointed joint guardian of the temporalities of the see of Coventry and Lichfield for the duration of the vacancy caused by the death of Bishop Catterick. This brought him into contact with the cathedral authorities at Lichfield, and three years later, when the dean sued him for two messuages in Brewood, Staffordshire, the court expressed the suspicion that there had been collusion between the two to infringe the Statute of Mortmain. Although he was only, so far as is known, returned to Parliament once, Lee attended the Shropshire elections of 1415, 1419 and 1421 (May), and in the meantime in the Parliament of 1420 he acted as one of the proxies of Bishop Lancaster of St. Asaph. Throughout his career Lee was very litigious on his own account, prosecuting many suits over land and for the recovery of debts, including one of £5 from (Sir) Rustin Villeneuve’s widow, Joan. He died shortly before 27 Nov. 1425 when proceedings in one such suit were terminated at the news of his death.