Gaius Caligua, Richard the II, Ivan the IV or Henry the VIII?

a) Gaius Caligua (12-41 A.D.) b) Richard II (1377-1399) c) Henry VIII (1491-1547) d) Ivan IV (1547-1584) e) all of the above

Gaius Caligula (12–41)

"There are plenty of other contenders for worst Roman Emperor – Nero and Commodus for example – but Caligula’s mad reign sets a high standard. After a promising start to his reign he seems to have set out specifically to intimidate and humiliate the senate and high command of the army, and he gave grave offence, not least in Jerusalem, by declaring himself a god; even the Romans normally only recognised deification after death.

"Caligula instituted a reign of terror through arbitrary arrest for treason, much as his predecessor Tiberius had done; it was also widely rumoured that he was engaged in incest with his sisters and that he lived a life of sexual debauchery, and this may well be true. The story of his making his horse a consul, meanwhile, may have been exaggerated, but it was not out of character.

"Caligula’s unforgivable mistake was to jeopardise Rome’s military reputation by declaring a sort of surreal war on the sea, ordering his soldiers to wade in and slash at the waves with their swords and collecting chests full of seashells as the spoils of his ‘victory’ over the god Neptune, king of the sea and by his failed campaign against the Germans, for which he still awarded himself a triumph. He was assassinated by the Praetorian Guard in AD 41…"

King Richard II (1377–1399)

"Richard II has good reason to feel grateful towards Shakespeare, who portrayed this startlingly incompetent monarch as a tragic figure; a victim of circumstances and of others’ machinations rather than the vain, self-regarding author of his own downfall he actually was.

"Learning nothing from the disastrous precedent of Edward II, Richard II alienated the nobility by gathering a bunch of cronies around him and then ended up in confrontation with parliament over his demands for money.

"His reign descended into a game of political manoeuvre between himself and his much more able and impressive uncle, John of Gaunt, before degenerating into a gory grudge match between Richard and the five Lords Appellant, whom he either had killed or forced into exile…"

Ivan IV ‘the Terrible’ (1547–1584)

"Prince Ivan Vassilyevitch grew up at the hazardous court of Moscow, his life often in danger from the rivalry of the boyars – nobles. It gave him a lifelong hatred of the nobility and a deep streak of ruthless cruelty – aged 13 he had one boyar eaten alive by dogs.

"Ivan was Prince of Muscovy from 1533, and in 1547 he was crowned Tsar (Emperor) of all Russia – the first ruler to hold the title. He crushed the boyars, stealing their lands to give to his own followers; he also condemned millions of Russians to a permanent state of serfdom.

"Ivan took a vast area of Russia as his personal domain patrolled by a mounted police force with carte blanche to arrest and execute as they liked. Distrusting the city of Novgorod he had it violently sacked and its inhabitants massacred, and he embarked on a disastrous and ultimately unsuccessful series of wars with Russia’s neighbours.

"Ivan beat up his own pregnant daughter-in-law and killed his son in a fit of rage... His ruthlessness, paranoia and taste for blood earn him his place in this list” (History Extra). 

Henry VIII (1491 - 1547)

"More than 60 writers were surveyed by the Historical Writers Association (HWA), with Henry VIII taking 20% of the vote to find the worst monarch and criticised for a wide range of crimes: he was 'obsessive', 'syphilitic' and a 'self-indulgent wife murderer and tyrant', according to respondents.

'Robert Wilton, the author of The Spider of Sarajevo, called the Tudor king 'a gross man-child, wilfully and capriciously dangerous to everything around him including the country', adding that psychologically, Henry 'barely made it out of infancy, let alone adolescence, and ruled with little more policy than petulant self-gratification…'" (The Guardian).