‘Thrice an under sheriff, and ever a knave’ seems to have been a generally understood expression at the turn of the 17th century. Sir John Harington, in his famous work A New Discourse of a Stale Subject, called the Metamorphosis of Ajax (1596), describes a dream in which ‘there came to me a nimble dapper fellow (I cannot hit on his name); one that hath pretty pettifogging skill in the law, and hath been an under sheriff (but not thrice), and is now in the nature of an attorney’. In a note, Harington cites the saying, to point out that the man in his dream, having not been Under Sheriff three times, is not a knave (he may have meant ‘not yet’). Similarly, in John Marston’s play The Malcontent (1604), the character Malevole responds to the insult of being an ‘arrant knave’ by saying ‘I have been twice an under-sheriff’, i.e. not three times.
It is perhaps not surprising that Under Sheriffs had a poor reputation, because they and the bailiffs (for whom no one has a good word either) did much of the legwork on behalf of the High Sheriff. Francis Lenton, in his entertaining Characterismi (1631), described Under Sheriffs as ‘the feare and terror of all debtors’. Until the passing of the Courts Act 2003, High Sheriffs still had the duty of executing High Court Writs, something that in practice was carried out by the Under Sheriff on the High Sheriff’s behalf. (The job is now done by High Court Enforcement Officers, including a firm called ‘The Sheriffs Office’.)
There have probably been Under Sheriffs for as long as there have been Sheriffs. We know the names of some of Essex’s Under Sheriffs in the late 12th and early 13th century, and it may be that one or two of those (John de Corherde or Cornerthe, John de Nevill) served in both capacities.
J. B. Gilder’s history of Gepp & Sons gives a very good account of the role of the Under Sheriff in modern times, including a list of Under Sheriffs of Essex since 1770. Essex has been remarkably fortunate that Gepps have been willing to provide successive Under Sheriffs, starting with T. F. Gepp in 1827, succeeded by C. B. O. Gepp in 1883, W. P. Gepp in 1907, H. H. Gepp in 1908, A. D. P. Thompson in 1946, T. C. Gepp in 1963, Jonathan Douglas-Hughes in 1988, and Roger Brice in 2014, with only a very small number of ‘interlopers’.
As well as being on duty alongside the High Sheriff during the Assizes, the Under Sheriff undertook much of the organization of parliamentary elections, arranged and attended the execution of prisoners found guilty of capital offences, and collected debts for the Crown (for which the Under Sheriff often received a percentage of anything he received in payment). In the early 20th century Gepp & Sons seized a whale that had beached itself in the River Crouch, and a Boeing 707 belonging to the President of Liberia.
It goes without saying that ‘Thrice an under sheriff, and ever a knave’ does not apply to Essex.