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After the victory of Edward's forces at Mortimer's Cross, Jasper and the Earl of Wiltshire fled in disguise. Jasper returned to Pembroke and tried to rally the spirits of the Lancastrian supporters.

At the same time, Margaret of Anjou and her son, Prince Edward, were moving south after their victory at Wakefield. They met the Yorkist forces at St. Albans and were victorious. Margaret and son were reunited with Henry VI, who had been a prisoner since the summer of 1460.

With Margaret's troops marching toward London, it was hoped that Jasper Tudor could raise enough forces in the west and the two Lancastrian armies could attack the combined Yorkist forces of the Earl of Warwick and march from either side. However, Jasper wasn't able to raise his army in time and Margaret's army lost popular support when they began pillaging and looting after their victory at St. Albans. She was forced to withdraw to Yorkshire.

Meanwhile, London welcomed the Yorkist faction and the Earl of March was proclaimed King on March 4, 1461. Edward IV kept pursuing the Lancastrian forces and handed them another defeat, this time at Towton. Henry VI, Queen Margaret and Prince Edward fled to safety in Scotland.

Meanwhile, Jasper Tudor was left vulnerable in Wales. Sir William Herbert was given the authority to seize the properties of Jasper Tudor throughout England and Wales. Parliament officially stripped him, as well as many loyal to Henry VI, of his properties with acts of attainder.

Jasper continued to try to raise support for the Lancastrians in Wales, but was eventually forced to flee to Scotland, along with the Duke of Exeter, who had survived from the battle at Towton.

When Sir William Herbert took Jasper's former residence of Pembroke, he found inside the four year old Earl of Richmond, Henry Tudor. The boy was taken into Herbert's custody, but was treated well and looked after by Herbert's wife, Anne Devereux at Raglan Castle. At some point, Herbert sought to marry the young Earl to his daughter Maud. Henry apparently felt little or no hostility toward Anne Devereux since he still regarded her with affection even after becoming king 25 years later. Henry was still addressed as the Earl of Richmond, even though the actual estates of the Earldom had been given to George, Duke of Clarence, brother of Edward IV.

While with the Herberts, Henry was educated by two Oxford graduates, Edward Haseley and Andrew Scot, both of whom were remembered by Henry after he became King. Other instruction was provided by Sir Hugh Johns, who was also remembered with a gift by Henry when he was King.

Henry Tudor's mother, Margaret Beaufort, was not given care of her son. She and her husband, Henry Stafford, lived at Bourne (Lincolnshire) and Woking (Surrey). Margaret was still allowed to correspond with her son and visited him at Raglan at least once.

Plots began to arise against the Yorkist crown. One ambitious plot was uncovered and John de Vere, Earl of Oxford and his son were arrested and executed for treason. In preparation for the planned attack, Jasper Tudor had gone to Brittany. After the plot was exposed, he went to King Louis XI of France looking for support. Margaret of Anjou also joined him there and she managed to get the King to agree to an alliance with the Lancastrians. Jasper had been traveling between Wales, Scotland, Brittany and France on behalf of the cause. Margaret had basically put Calais up as collateral for a loan from the King of France.

The Queen returned to Scotland and from there she, Henry VI and others sailed south to Northumberland and took over Bamborough and Alnwick Castles. Jasper Tudor was one of the Lancastrians left to hold Bamborough. However, upon news of the approaching army led by Edward IV, Henry VI, the Queen and their supporters fled back to Scotland. Bamborough surrendered Christmas Eve 1462. Jasper returned to Scotland.

Margaret of Anjou traveled again to France to try to prevent King Louis from reconciling with Edward IV, but she failed. Jasper Tudor probably accompanied the Queen to France but returned to Scotland without her in December 1463. Margaret remained in France until 1470.

Jasper tried to raise a force to land in Wales in 1464, but they met with little success. Parts of Wales were still sympathetic to the Lancastrians, especially in the west and northwest. Harlech Castle on the west coast remained in Lancastrian hands until 1468.

In 1467-8, the political situation began to turn back to the favor of the Lancastrians. In early 1468, Edward IV made alliances with the Dukes of Brittany and Burgundy, much to the discomfort of the King of France. Looking for a way to embarrass Edward IV, Louis XI of France gave some money and three ships to Jasper Tudor for his trip to Wales in June 1468. However, this was not enough support for Jasper to be able to inflict any real damage. Jasper probably landed at the Dyfi estuary near Harlech and made his way across north Wales toward Denbigh. It is written that by the time he reached Denbigh his force had grown to 2000 men. Jasper seized the castle and burned it.

The campaign spurred Edward IV into action and sent orders to Lord Herbert to raise a force and attack the Lancastrian-held Harlech Castle. Confronted with two wings of soldiers (one from the east and the other from the south), Harlech surrendered on August 14, 1468. Jasper Tudor managed to once again avoid being captured. As a further humiliation to Jasper, King Edward gave the Earldom of Pembroke to Lord Herbert.

Over time, Edward IV had been alienating his most powerful supporter - Richard Neville, the Earl of Warwick (known as 'The Kingmaker') because of the favors given to the family of his wife, Elizabeth Woodville. Warwick raised an army which defeated the King's force, led by Lord Herbert, the new Earl of Pembroke. Herbert was captured and executed along with his brother, leaving the earldom open once more. This divide in the Yorkist faction raised another moment of opportunity for the Lancastrians.

For almost a year, ending in September 1470, Jasper Tudor was in France in the service of King Louis.

The Earl of Warwick had joined with George, Duke of Clarence (brother of Edward IV) and gone to France in May 1470. Louis and Warwick began working on a plan to restore Henry VI to the throne. The deposed King had been captured in 1465 and was in the hands of the Yorkist King Edward IV. Warwick also proposed a marriage between his daughter Anne and Henry's son, Prince Edward.

Margaret of Anjou, who was still in France with her son, at first was not very enthusiastic about the plot. It is understandable that she would not be overly supportive of Warwick, since he had played a major role in the move against Henry VI ten years earlier. But Louis was able to convince her to go along with the plan.

Warwick and Jasper Tudor were to go to England, followed by Margaret, Prince Edward and Anne Neville, who was now betrothed to the Prince. Jasper was to go to Wales and Warwick to London. They landed at Dartmouth and Plymouth and Jasper set off to Wales to raise his forces.

Henry Tudor was still in the Herbert household now under the protection of Lord Herbert's widow. At some point while Jasper and Warwick began their movements against Edward IV, Henry Tudor was taken into the protection of of Sir Richard Corbet, who was able to convey the boy to his uncle.

Edward IV was in Yorkshire and was not going to be able to reach London before the Earl of Warwick. On October 2, 1470, Edward IV fled to Holland. Henry VI was released from the Tower of London and restored to the throne.

Henry Tudor and his mother Margaret Beaufort were reunited and stayed together for over a week at the Beaufort residence at Woking in November 1470. After that they parted on November 12, and Henry left to rejoin his uncle. It is probable that the next time the teenager saw his mother was after the Battle of Bosworth Field and he had become King Henry VII.

It is recorded that at about this time there was a meeting between Henry VI and young Henry Tudor. The most famous telling is from Shakespeare, but other chronicles have also noted the meeting (and it was this material that Shakespeare drew on). In this interview, Henry VI was said to have told the boy that he would one day sit on the throne of England.

It would not have been too out of the ordinary for Henry to have an audience with the 13 year old Earl of Richmond, but it would have been odd for him to tell the boy he would be king. Henry VI did have a son to succeed him, although the boy was in France with his mother. Whether the king truly made the prophecy will never be known, but it did eventually come to pass.

Parliament met for a month at the end of 1470 to undo Edward IV's work and restoration of the Lancastrians, including Jasper Tudor's title of Earl of Pembroke, and the associated lands and estates. Jasper was given other estates which greatly increased his holdings and power.

Unfortunately for the young Henry, his holdings of the Richmond estates remained in the hands of the Duke of Clarence, although the teenager still held the title of Earl of Richmond. Jasper was put in control of the areas of Wales where Edward IV still had support - the borderlands and southeast Wales.

The restoration of Henry VI proved to be short-lived. Edward IV landed in Yorkshire on March 12, 1471 and he reached London a month later. On April 14, he fought Warwick at the Battle of Barnet, where the Earl was killed. Henry VI was captured once again.

Margaret of Anjou and Prince Edward returned from France, not knowing of the recent turn of events. Once she received the news, the strong-willed Queen began gathering troops to presumably meet Jasper Tudor at the Welsh borderlands. Edward IV left London to pursue Queen Margaret and their forces met near the town of Tewksbury in one of the bloodiest battles of the Wars of the Roses. The day was a disaster for the Lancastrians. One of the many killed in the battle was the young Prince Edward, Henry VI's only heir. Margaret was captured. Jasper Tudor (presumably with his nephew) were unable to reach Queen Margaret in time and the Lancastrian's cause was near complete collapse. To make matters worse, Henry VI died on May 21 in the Tower of London under mysterious circumstances.