Bailiffe belonged to a long line of lawyers. His grandfather, a Somerset man, was a member of Lyon’s Inn, while his father, who leased the Monkton estate at Chippenham from the 1st earl of Hertford, was a Middle Temple barrister.
Bailiffe was returned for Chippenham to the 1621 Parliament on the strength of his family’s local influence. His father had sat for the borough in 1572, while his brother Henry, who was Chippenham’s wealthiest resident, had almost secured election there in 1614.
Bailiffe’s later life was dominated by his onerous duties at the Middle Temple. Described by a contemporary as a ‘discreet and painful officer to the whole house’, he became under-treasurer in 1619, abandoning his career at the bar. When the Inn’s administration was reorganized seven years later, Bailiffe took on many of the functions previously performed by the annually elected treasurer, including sole responsibility for finance, the registering of new students, and the supervision of building works, such as a six-storey block of new chambers constructed in 1637-8. In return for this work, he was allowed £20 a year and assorted other perquisites. He also received rent from two shops and some chambers that he had built within the Temple in 1620.
Bailiffe’s final years were overshadowed by financial problems. His Middle Temple income suffered when his private shops and chambers were demolished around 1640, and he spent several years seeking compensation.
