Harold Umbridge was the son of a minor lord (Myran Umbridge) born in Everglow City in 940AE. He now lives as Lord Umbridge of Westgate, a small series of rocky islands north of Briochi. He is head of House Umbridge.
At the age of 16 (956AE), while still under his father in Elverglow, he was betrothed to Amayl Heartstone-Rodin, a merchant king's young daughter of the same age. However, the girl (whom he had never met) was kidnapped by pirates en route to their wedding. Harold, sensing an opportunity to prove his grit, set out on an expedition with his father's men to rescue the fair maiden. But for many years, they did not succeed and eventually the search was called off.
In his time on the waters, Harold stumbled across the islands which would later become known as Westgate. Previously uninhabited due to their sheer cliffs and high elevation, they had been deemed undesirable for some time. But at age 22 (962AE), Harold and his loyal crew climbed the treacherous rock faces and found the ruins of an ancient city. For some reason, even the High Elves and the Drow hadn't heard of this dead civilization. It had died as it had lived - without a peep.
Harold claimed the land and the ruins and had become Lord Umbridge by the time he was 24 (264AE). His aging father remained in Everglow City for medical care and to act as a proxy in the Senate.
Lord Umbridge gained a reputation while searching for his lost betrothed. Tales of his 'great love' for this woman spread along the grapevine and his story became a tragic romance of lost love. He always hated this, and that his father encouraged it by writing a damned book.
Finally, at the age of 30 (970AE) he stumbled upon his betrothed quite by accident. He had never expected her to turn back up again, but on a raid into an infamous pirate's den (Nazaret Malabre✞) he found Amayl as a slave. Freeing her and killing Nazaret, he took her back to her father and proposed. But she turned him down.
Offended and exasperated from all the years he had put up with the ridicule of chasing one woman for glory and duty (even if it was just her corpse he found), he left and married a commoner (Margeret Umbridge nee Kilburn, born 956 AE) in Westgate. But he felt he had become discredited by Amayl. His story had fizzled out into something very anti-climatic.
At his and Margeret's wedding in 971 AE, he met Margeret's then-pregnant sister Millendra Rodin and her husband, Greyson Rodin. There was no further familial contact from that point as he and Greyson didn't get along.
Harold's son, Arthur, bedded a chambermaid when he was sixteen and got her pregnant (998AE). Shortly after the bastard babe was born, Arthur died from an illness. Harold took on the bastard, James Umbridge, and proclaimed him his heir along with giving him the family's name, seeing as his wife was unable to bear more children.
With the recent death of his wife, Harold is turning his attention back to Amayl, hoping to ruin her the way he feels she ruined him. He feels the end of his life approaching and wants to go out with a bang, and make the Umbridge House worthy of respect again.
His son, Arthur✞, was born in 976AE.
His bastard grandson, James, was born in 998.
Arthur✞ died in 999 from an illness.
Harold's wife, Margeret✞, died in 1014.