[3][4][5] He is chiefly remembered as the companion of King Charles II when the fugitive monarch hid in the Royal Oak following his defeat at the Battle of Worcester.

After the outbreak of hostilities in 1642 Careless raised a troop of cavalry to fight for Charles I, which he commanded as a captain in the regiment of Thomas Leveson.

Careless (as William Carlis) has been listed as one of the two captains of Leveson's Horse present at the Bolton Massacre, an action controversial for the indiscriminate killing of Parliamentarian defenders and civilian inhabitants.

[9] Following this serious Royalist defeat Careless is next recorded in his native area of the English Midlands, when in December 1644 he was captured in a skirmish with Parliamentarian forces near Wolverhampton.

[10] After his release Careless served in Ireland, lived in Lower Germany (Netherlands) for a time and became an officer in the Spanish army.

Careless fought to the end, covering the King's flight alongside a handful of others including the Earl of Cleveland, Sir James Hamilton, Colonel Thomas Wogan and Captains Hornyhold, Giffard, and Kemble.

[14] Following his catastrophic defeat, King Charles sought refuge at Boscobel House where, as he related to Samuel Pepys in 1680, he met Major Careless.

Careless, who was a local man,[15] suggested that the house was unsafe and recommended that the king hide in a large pollarded oak tree in the woodlands of Boscobel (6 September 1651).

The king and Careless took some food and drink into the tree and were gratified that Parliamentarian soldiers searched the woodland intensively without detecting them.

[16][17][18] A contemporary armorial locket containing a miniature portrait of William Careless is in the collection of the Victoria and Albert Museum, London, (see "External links" below).

[24] He returned to England with Charles II in 1660, and after the Restoration Careless was granted (with 2 others) the lucrative proceeds of tax on hay and straw brought into London and Westminster, the right to sell ballast to shipping on the Thames and the office of inspector of livery horsekeepers (1661).

Charles II was persuaded that the new order of chivalry would prove politically and socially divisive as it only rewarded those who had aided him in adversity and those who were ardent Royalists.

[27] Gentlemen of the Privy Chamber were empowered to execute the King's verbal command without producing any written order; their person and character being deemed sufficient authority.

[28] Careless was evidently loyal to King Charles' successor, James II, as he was paid a bounty of £300 from that monarch's secret service fund in 1687.

Colonel William Careless is recorded as living in Hallow, Worcestershire in the 1680s; he died in London, and was buried in his native Brewood, 28 May 1689.

The medal shows (obverse) a view of the walls and fortifications of Worcester with defenders; outside, Charles on horseback attended by the four Penderels and Yates, and before him a company of soldiers (British Museum catalogue: MB1p394.19).

However, of the payment, from the various sources of income bestowed by Charles II, which was granted to the descendants of the heirs of William Careless some was suspended by the British government in 1822, and the remainder early in the 20th century.