Medieval history is full of singularly unlucky families--the Despensers, whose lords each died violently, young, or both, being one of the primary examples. The de la Pole family is another ill-fated clan.
It probably didn't look at all bad for the de la Poles initially. William, who died in June 1366, had been a financier to the crown as well as a successful wool merchant. Though William's activities proved controversial, and he was ultimately forced to forgive the outstanding royal debts owed him, he nonetheless died wealthy and in his bed.
William's eldest son, Michael, devoted himself to a military career instead of to the wool business. He served under both the Black Prince and John of Gaunt, and won the favor of the Black Prince's son Richard II, who ultimately made him the Earl of Suffolk in 1385, when Michael was 55. Unfortunately, being a favorite of Richard II was a risky business, and he and other royal advisers were accused of treason. Michael fled the country, eventually reaching Paris, and was convicted of treason in his absence in 1388. He died in Paris, still in exile, in 1389, leaving behind six children, including his heir, another Michael.
The younger Michael was restored to the earldom of Suffolk in 1398. He served the crown militarily but largely stayed far away from national politics. In 1415, he accompanied Henry V on his campaign in France, where he fell victim to the dysentery that plagued the soldiers. He died on September 17, 1415, during the siege of Harfleur. The earldom passed to his eldest son, yet another Michael, who enjoyed his title for only a few weeks. He died at Agincourt on October 25, 1415. He and the Duke of York had been the only English noblemen who fell there. Thus, Michael's younger brother William became the fourth Earl of Suffolk, just nine days after his nineteenth birthday.
William had been wounded at Harfleur and had been sent home to recuperate; thus, he missed Agincourt. He returned to military service in France in 1417, however, and remained abroad almost continuously. On June 12, 1429, at Jargeau, he met disaster in the person of Joan of Arc, who defeated his forces. William's younger brother Alexander was killed that day, and another brother, John, was taken captive and died of his wounds shortly thereafter. William himself was captured. He remained in captivity until 1430, when he was released on a promise to repay his ransom, which he later claimed was 20,000 pounds. He was required to leave his only surviving brother, Thomas, as a hostage in his place. Thomas himself died in captivity.
In 1430, William returned to England, where he gradually became a favorite of the maturing Henry VI, with disastrous results. William was sent in 1444 to negotiate Henry's marriage to the 14-year-old Margaret of Anjou; following William's return to England, a grateful Henry VI made him Marquess of Suffolk. Four years later, in June 1448, William was made Duke of Suffolk. This was singularly bad timing on Henry VI's part, for in 1445 Henry had secretly promised to cede Maine to the French. The promise, which proved deeply unpopular, had at last been carried out in March 1448.
Suffolk had had the unenviable task of facilitating the cessation of Maine. Apparently in an attempt to head off further losses, he came up with a scheme to force Brittany into an alliance with England by seizing the wealthy Breton town of Fougères. This scheme, which looks absurd to modern eyes, must have made sense at the time, for Parliament in 1449 was all approval when word of the successful seizure of the town arrived. Unfortunately, the scheme backfired miserably by causing Brittany to turn to France and by giving France the opportunity to break its truce with England. Town by town, Normandy fell back into French hands.
With Maine ceded and Normandy all but lost, blame had to be placed somewhere, and as Henry VI's chief minister, Suffolk was the natural scapegoat. In early 1450, the Commons accused Suffolk of treason; among the charges was that he had secretly promised to hand over Maine (in fact, the secret promise was made by Henry, and other lords reluctantly acquiesced) and that he had plotted to depose Henry VI and raise his own son to the throne by dint of the son's marriage to little Margaret Beaufort.
Suffolk submitted himself to judgment by Henry VI himself, who held him "neither declared nor charged" on the treason charges. With regard to a series of lesser charges, mostly relating to finances, Henry VI ordered that Suffolk absent himself from England for five years.
The sentence of banishment was undoubtedly meant by Henry VI to save Suffolk from a worse fate, but it failed miserably. While heading into exile, Suffolk was intercepted by a vessel named Nicholas of the Tower, forced on board, and subjected to a mock trial by its crew. Not surprisingly, he was found guilty. Having been allowed to spend time with his confessor, he was taken into a smaller boat on May 2, 1450, and beheaded with six strokes of a rusty sword. His head and body were dumped on the Dover shore. Thus, William, his four brothers, and his father had each fallen in some way that was connected with the war in France.
William de la Pole had only one legitimate child: his son, John, who was just seven when his father was murdered. He succeeded to his father's dukedom. His child marriage to little Margaret Beaufort having been annulled (leaving Margaret free to remarry and give birth to the future Henry Tudor), Duke John, as we will call him, married Elizabeth, one of the daughters of the Duke of York. Though this made him the brother-in-law of the future King Edward IV, he never played a leading role in the Yorkist government despite his loyalty to the new king. He seems to neither have helped nor hindered Richard III's ascent to the throne. His transition to Henry VII's reign was equally smooth; he was at Henry's first Parliament.
Duke John's sons were another story. His eldest son, another John, the Earl of Lincoln, might have been intended by Richard III, whose only legitimate son died in 1484, to succeed him on the throne were Richard to die without legitimate heirs. Lincoln was apparently at the Battle of Bosworth, but he was not punished by Henry VII, whose coronation he attended. In 1487, however, he became embroiled in the Lambert Simnel conspiracy and led troops against Henry VII at Stoke, where he was killed on June 16, 1487. Lincoln, who was married but childless, was posthumously attainted, but his father was exempted. Duke John continued to serve on commissions for Henry VII until his death in 1492. His heir was his next surviving son, Edmund.
Henry VII's generosity toward Duke John did not extend to Edmund. The estates that had been settled by Duke John on Lincoln were forfeited to the crown upon the duke's death, and Edmund ultimately had to pay for the privilege of entering some of them. His income was insufficient to support a dukedom, but he was allowed to bear the title of Earl of Suffolk. Henry VII otherwise treated him well; he was made a Knight of the Garter in 1496 and served Henry militarily in 1497. Nonetheless, Edmund left England without royal license in 1501 and began plotting, along with his younger brother Richard, to seize the crown from Henry VII. By 1506, however, he was fed up with life on the run and was allowed to return to England, albeit as a prisoner in the Tower.
Unfortunately for Edmund, his younger brother, Richard, remained abroad and plotting. Accordingly, a nervous Henry VIII had Edmund executed in 1513. Richard, now calling himself the Duke of Suffolk and also known as "the White Rose," continued to make trouble for Henry abroad, where he served as a soldier. On February 25, 1525, he was killed at Pavia while fighting for François I against Charles V.
Two of the de la Pole brothers died of natural causes: Edward had died in 1485, having become Archdeacon of Richmond, and Humphrey, rector of Hingham in Norfolk, died in 1513. The remaining brother, William, was arguably the most unfortunate of Duke John's offspring. Sent to the Tower in 1502 on the ground that he was plotting with his brothers Edmund and Richard, he remained there for 37 years, dying as a prisoner some time before November 1539. With him, the male line of the de la Pole family died out.