Henry I (1100-1135)
Oh, Henry I. What a card. I mean, besides the whole assassination/usurpation thing, he set the record for the number of illegitimate children fathered by an English king (nineteen--that we know of!).
This is yet another death story. What do you want from me? It was the Middle Ages. This one is really kind of a big deal: the sinking of the White Ship.
Now, prolific as Henry was, he only had two legitimate children: Matilda (remember her for later) and William the Aetheling ("Aetheling" being a sweet Old English word for prince). In 1120, Henry and some of his children (including William but not Matilda) returned to England from Normandy. The kids rode in the White Ship, the fastest ship in the fleet and also the scene of some raucous partying before departure. Unfortunately, the captain of the vessel got drunk and--I'm sure you can see where this is going--the ship sank in the English Channel.
Only two men grabbed hold of a spar from which the sail hung and, clinging to it for the greater part of the night, waited for help to come from any quarter. One was a butcher of Rouen named Berold, and the other a noble lad called Geoffrey . . . The night was frosty, so that the young man . . . finally lost his grip and . . . fell back to perish in the sea and was never seen again. But Berold, who was the poorest of all and was dressed in a pelisse made of rams' skins, was the only one of the great company to see the day . . .
The sad news spread swiftly from mouth to mouth through the crowds along the sea coast . . . but that day no one dared announce it to the anxious king, who earnestly asked for news . . . However, on the following day, by a wise plan of the Count Theobald's, a boy threw himself, weeping, at the king's feet, and the king learned from him that the cause of his grief was the wreck of the White Ship. Immediately Henry fell to the ground overcome with anguish, and after being helped to his feet by friends and led into a private room, gave way to bitter laments.Orderic Vitalis, via The Oxford Book of Royal Anecdotes
The Oxford Book of Royal Anecdotes also notes that Henry I's reputation was embellished by "a respectable Victorian legend" that he never smiled again.
And this has been your (rather long) Monday Monarch Moment.