Philippa lost both her parents at a very young age, but her future was provided for (eventually) by her marriage to John Hastings, Earl of Pembroke after his rather awkward divorce from Elizabeth of Lancaster. Pembroke was exceedingly rich, but he never came into his own, as he was tragically killed in December 1389 at the age of 17 while practising jousting at court.
According to the Westminster Chronicle, he was riding against Sir John St. John (probably the same John St. John who was later a Despenser and royal retainer) when St. John, in obedience to the instructor supervising Pembroke, threw down his lance. The handle of the lance stuck in the ground and the point pierced Pembroke’s groin. The wound proved mortal and within an hour the young earl was dead.
Pembroke had been a popular youth and if the Chronicler is to be trusted the whole court was devastated, the Queen weeping in her chamber for days. St. John fled before the sorrow turned to anger, but was pardoned the following year. (The death was a tragic accident, after all.)
Philippa’s marriage was possibly not consummated – she was only fourteen – but whether it was or not she was still entitled to dower, and a very extensive dower too. She became overnight one of the richest women in England.
The following year, on 15 August, Philippa married the widower, Richard Fitzalan, Earl of Arundel, who was very much her senior. (Tell me Richard, what first attracted you to incredibly wealthy Philippa?) This was done in secret, without the King’s consent, and they were fined. However, such a fine was chicken feed to a man like Arundel, who was enormously wealthy, having inherited a vast fortune from his father.
Although the match was almost certainly based on financial (and possibly dynastic) considerations, Arundel and Philippa seem to have loved one another, hard though it is to attribute such an emotion to a man of flint such as Richard Fitzalan. They apparently dined together in private by candlelight supplied by an expensive candelabra and Arundel went so far as to rename one of his many castles ‘Castle Philippe‘, which is to say Philippa Castle. I cannot offhand think of a similar example of husbandly devotion going to the extreme of renaming a castle.
They had one son, John, Philippa’s only child, but he did not survive long, unfortunately.
Arundel had, of course, made himself extremely unpopular with Richard II, and in the 1390s also spent time in violent disputes with the King’s uncle, John of Gaunt. Reckoning was not far off, and in 1397 Arundel was arrested, tried and executed for high treason.
Philippa remained a wealthy and a young woman, and at some point after April 1398 and before 24 November 1399 she married Thomas Poynings, Lord St. John of Basing. He was a good twenty years her elder and had buried a previous wife.
Sadly, he was to bury Philippa also. She died on 24 September 1401. It was possibly a result of childbirth, but this is mere guesswork.
Philippa was buried at Boxgrove Priory, near Lewes, Sussex. Many years later, when he died, Thomas Poynings asked to lie next to her, so she was clearly not forgotten.