Named after a farm situated a mile to the east of Bishop’s Castle, the Oakeleys were by the early Stuart period a prolific family with branches on both sides of the Welsh border. Details of the family pedigree remain obscure, but the MP had several namesakes among his relatives, including a Salopian who obtained an MA from St. John’s College, Oxford in 1593, a parliamentarian from Bradstow, Shropshire and another man whose father, Rowland Oakeley of Pentre Nant, Montgomeryshire, married one of the MP’s sisters. Despite claims to a lengthy ancestry, Oakeley’s landed inheritance was valued at a modest £55 a year in 1646, which obliged him to earn his way in the world.
As a ‘postmaster’ [student] at Merton, Oxford in 1609, Oakeley introduced himself to the lawyer James Whitelocke* with a Latin epistle, and was hired as his clerk. In his spare time Oakeley studied the law, following in his master’s footsteps at New Inn and the Middle Temple, and within a few years Whitelocke allowed him to deputize as steward of Westminster Abbey. In 1619 he resigned his position to finish his legal studies, during which time he lived in Whitelocke’s chambers at the Middle Temple and encouraged Bulstrode Whitelocke* to enter the legal profession. Although called to the bar in Michaelmas term 1621 he never practised, as he became secretary to Dean John Williams of Westminster upon the latter’s appointment as lord keeper in July 1621.
As a long-term absentee, Oakeley had relatively little influence in Shropshire, and it was presumably Williams, an active parliamentary patron, or perhaps Whitelocke (then recorder), who recommended him to the electors of Bishop’s Castle at the general election of 1624. Williams’ discharge of his judicial functions came under scrutiny in the Commons, which prompted Oakeley’s only recorded speech. This concerned the Sutton rectory case, in which Williams, as lord keeper, had appointed an incumbent by lapse in defiance of a rival claim by the Court of Wards. After lengthy debate on 21 Apr., a consensus emerged that Williams had acted improperly but without malice, and Oakeley intervened with an offer from his master to remove his candidate and to procure a fresh grant to the rival nominee.
By the time of the next election in May 1625 Williams’s political star was fading rapidly, and Oakeley was replaced at Bishop’s Castle by William Blunden, one of the borough’s capital burgesses. Williams was finally sacked in November 1625, which gave him free rein to support the attacks mounted against the duke of Buckingham in Parliament the following spring. At this election he found Oakeley a seat at Boston, where the corporation obliged their bishop in return for a licence to demolish a derelict church. On 22 Apr. 1626 Oakeley was cited as a witness for some of the allegations made against Buckingham, although his testimony was not used in the duke’s impeachment. Two years later Oakeley was returned by the Boston corporation once again, after a poll in which he beat his rival, Sir Anthony Irby*, by 15 voices to 14. However, on 8 May the Commons overturned this verdict, ruling that the franchise be extended to the freemen and the seat be awarded to Irby.
Williams retained his ecclesiastical offices after his removal as lord keeper, and in 1626 he appointed Oakeley and one of his brothers joint receivers-general at Westminster Abbey, a post the two men held until 1642. By that time Oakeley had secured a lease of the abbey’s estate at Launton, Oxfordshire, worth £100 a year, which became his main residence.
Oakeley retained his chambers at the Middle Temple, and may have been taken into preventive custody at Westminster upon the outbreak of the Second Civil War, but the authorities gave him no further trouble thereafter. In the last year of his life he was dragged into a lawsuit over the inheritance to Williams’ Huntingdonshire estates, claimed by Sir Owen Wynn of Gwydir, Caernarvonshire in lieu of the dowry due upon his marriage to Williams’s niece. Oakeley apparently sold the Huntingdonshire estates back to the Cromwell family shortly before his death on 26 Sept. 1653. Administration of his estates was granted to his son and heir William†, who represented Bishop’s Castle in four parliaments during the latter half of the century.