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The best known, and indeed the most infamous of all British judges, Jeffreys was born in Wrexham, Denbighshire of noble parentage, and educated at Westminster School and Trinity College, Cambridge. He was admitted to the Inner Temple in May 1663, and called to the bar five years later.

He lost no opportunity of ingratiating himself with members of the corporation, and quickly rose to high office. In 1677 he received a knighthood and was appointed Solicitor General to the Duke of York. The next year ''he was; called to the bench of the Inner Temple. In 1681 he received a baronetcy and the king cleared the way to his appointment as Lord Chief Justice (1683), and membership of the Privy Council. Our portrait dates from this period. He took his seat in the House of Lords in May 1685, and as no Chief Justice had ever been made a lord of parliament this was an exceptional mark of royal approbation. Jeffreys was now the virtual ruler of the city, and had practically superseded the lord keeper in his political functions -as well as having the whole legal patronage in his hands.

On 8th June 1685, two days after the Battle of Sedgemoor, the commission was issued for the Western Circuit with Jeffreys as its President and four other judges. This was to prove the basis for Jeffrey's fearsome reputation. The commission sat at Winchester, Salisbury, Exeter, Taunton, Wells and Bristol. The number of executions for high treason ordered by Jeffreys is thought to be 320. More than 800 rebels were imprisoned and Jeffreys himself appears to have amassed a considerable sum during the trials which became known as the bloody assizes.

He was appointed to the post of Lord Chancellor by a thankful James II in 1685, and when James fled the country in 1688, Jeffreys understandably disguised himself as a sailor and hid aboard a vessel moored off Wapping where he hoped to escape by sea. He rashly went ashore, and was recognised whilst drinking at a pub. An excited mob gathered and began pelting him but he was rescued by a company of train-bands and taken to the Lord Mayor who swooned when he saw it was Jeffreys. He was removed to the Tower at his own request to save him from the mob, and died a prisoner on 18th April 1689 at the age of 41.

Although a fearsome judge in criminal cases, he was said to have shown great impartiality and understanding in civil cases where there was no political axe to grind.