From an old postcard.

In 1460 Lord Dudley was elected as a Knight of the Garter and after his release, he quietly changed his allegiance to the House of York. At the Battle of Towton in 1461 he was rewarded for his participation on the side of Edward, Earl of March, son of Richard, Duke of York. On the 28th June that year, Edward IV was proclaimed King in London and Lord Dudley became Constable of the Tower of London.

Ex-King Henry was captured by Edward's forces in 1465 and imprisoned in the Tower of London. Henry was restored to the throne in 1470, but Edward took over again in 1471, killing Henry's only son and heir, Edward of Westminster, in battle and imprisoned Henry once again. Henry died in the Tower of London during the night of the 21st May, 1471, possibly killed on the orders of King Edward.

In 1477 to 1478, Lord Dudley was in France with his brother-in-law, the Earl of Arundel to negotiate the continuance of the peace treaty between England and France. In 1479, Lord Dudley’s wife, Elizabeth, died, and in 1483 his eldest son Edmund, also died. After King Edward’s death in 1483, Lord Dudley supported the new ruler, King Henry VII, the first monarch from the House of Tudor. Lord Dudley was given the manors of Northfield and Wiley, in Worcestershire and created Sheriff of Sussex after his part in the Battle of Bosworth Field, the last significant battle in the Wars of the Roses.

Lord Dudley died on the 30th September, 1487 at Dudley Castle. His will stated that he was to be buried in St. James Priory, Dudley, in a tomb costing no more than £20. Because his eldest son, Edmund, died before him, the barony was inherited by Edmund’s son, Edward.

Sir Edward Sutton, 2nd Baron Dudley, was born around 1460 and married Cicely Willoughby of Parham, at Worcester, on April 21st, 1478. She was just 15 years old. They had 15 children:

Edward Sutton’s mother was Joyce de Tiptoft, daughter of Sir John Tiptoft, 1st Baron Tiptoft. She died on the 18th October, 1485 in Dudley Castle. Edward benefited from his mother’s inheritance of the Tiptoft barony and also the Cherleton barony. He was elected as Knight of the Garter in the beginning of King Henry VIII's reign and was chamberlain to Princess Mary (later Queen Mary I) from 1525 to 1528.

Sir Edward Sutton, 2nd Baron Dudley, died on the 31st January, 1531 was succeeded by his son John, who was born in 1494 at Dudley Castle. By the 30th October, 1501 John was betrothed to Lady Cecily Grey, daughter of the 1st Marquess of Dorset. They married in about 1512 and had the following children:

John Sutton, 3rd Baron Dudley, was knighted on the 13th October, 1513, and became known as Lord Quondam, or Lord Has-been. He was in debt and mortgaged most of his estates to Sir John Dudley, afterwards Duke of Northumberland, for £2,000, for which he agreed to pay £400 yearly.

In 1532 Baron Dudley wrote to Cromwell begging him to use his influence with the king to persuade him to pay the £2,000 and to take in exchange the manor of Sedgley, worth £180 per year, for twenty years. The request was not granted and in 1553 he begged Cromwell to pay the £400 interest. In 1538 or 1539, Cromwell lent him £1,000. In 1535 He sold Dudley Castle and the manor of Dudley to his cousin, Sir John Dudley, who resided at the castle and added many extensions including the rebuilding of the whole residential block on the east side of the bailey.

After Northumberland's execution, Dudley Castle became crown property and in 1555 Queen Mary handed it over to Edward Sutton, 4th Baron Dudley. Edward was born in 1512 and obtained a commission as captain under his uncle Lord Leonard Grey in Ireland. In 1547 he joined the expedition into Scotland and was appointed governor of Hume Castle. He was a distinguished soldier who managed to regain the family estates.

He succeeded his father as Lord Dudley in 1553 and had three wives. The first was Katherine Brydges, daughter of John Brydges. They were married in 1556 and had two children, Anne, born in 1556, died in 1605, and Thomas. The following year after Katherine’s death in 1566, Edward married Jane Stanley, daughter of Edward Stanley, 3rd Earl of Derby. They had two children, Edward Dudley, who became the 5th Baron Dudley, born on the 17th September, 1567, died on the 23rd June, 1643, and John Dudley, born on the 30th November, 1569, died in 1644 or 1645. After Jane’s death he married Mary Howard, daughter of William, 1st Baron Howard, on the 16th December, 1571 at Whitehall Palace.

Mary Queen of Scots was forced to abdicate in 1567 and fled to England to seek the protection of her first cousin once removed, Queen Elizabeth I of England. Perceiving Mary as a threat, Elizabeth had her confined in various castles and manor houses in England. In 1575 Queen Elizabeth visited Dudley Castle. Possibly because the old great chamber had been converted into a spacious drawing room with two large double transomed six-light windows.

In 1585 Dudley Castle was considered to be suitable for use as a prison for Mary and so her jailer, Sir Amias Paulet, inspected the castle and decided that it was unsuitable for the purpose. He reported that there were not enough rooms, tables, cupboards and stools. Coal and wood was plentiful but had to be purchased and a barn would have to be converted to a stable for the horses. There were no inner chambers for servants, or staff, brewing vessels were decayed, the water supply had to come from outside the castle, and security could be a problem because some of the windows the surrounding park. He felt that the deep ditch would prevent her from escaping and that the buildings were very strong. In the end she was sent to the moated manor house at Chartley.

Edward Lord Dudley died in 1586 and was succeeded by his eldest son, also called Edward. Edward Dudley 5th Baron Dudley, was born on the 17th September, 1567. In 1580, at the age of 13, he was sent to Lincoln College, Oxford, and the following year married Theodosia Harington (1560 to 1650) of Exton, Rutland, who was about 5 years older. Theodosia Harington, who died in 1649 was the daughter of James Harington of Exton, Rutland, a lawyer and long-serving MP. The Harington family were the largest landowners in Rutland. 

Edward and Theodosia Sutton had one son and four daughters:

Edward also had a mistress, Elizabeth Tomlinson, with whom he had at least 12 illegitimate children, who he provided for. Elizabeth Tomlinson (1579 to 1629) was the daughter of local collier William Tomlinson and his wife Agnes. Their children were as follows:

The eldest child, Robert, was given a small estate at Netherton; Dud, an ironmaster, was given the lease of Chasepool Lodge in Swindon, Staffordshire; Jane, was grandmother to ironmaster Abraham Darby I.
Edward owned lands in Staffordshire and Worcestershire, as well as the manors of Dudley, Sedgley and Kingswinford, along with local ironworks.

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Edward moved to Himley Hall, then a moated manor house, with his mistress, Elizabeth Tomlinson and their children, leaving his wife Theodosia and their children in London. Edward left his wife with no financial support; the Privy Council became involved and the Star Chamber ordered Edward to pay his wife an allowance, as she was left "without provision of sustenance" whilst he lived with "a lewd and infamous woman".

Edward continued to leave his wife without money and in August 1597 was sent to Fleet Prison for non-payment of the allowance. He was only imprisoned for a few days and was released on condition that he give his wife the £66 that was owed to her since the Privy Council ruling. In addition to this, he was to pay £100 a year to Theodosia during her lifetime unless the couple were to reunite, as well as £10 a year for the education of each legitimate child. Less than eighteen months later Edward was again called to the Privy Council as he had failed to maintain the payments, sending Theodosia only one payment of £32.

Edward Dudley was knighted in 1584 but did not take his seat in the House of Lords until 1593. Lord Dudley ended-up in the Star Chamber, the court which sat at the royal Palace of Westminster.

Debts continued to grow, and by 1593 the estate had been forcibly possessed by the authorities. He fell out with his younger brother John, because Lord Dudley failed to pay him a promised annuity from their father’s estate. Dudley’s most bitter feud was with Gilbert Lyttelton, in the 1590s, over Prestwood Farm. He had Lyttelton forcibly removed and claimed the right to seize goods from Lyttelton’s estates and took sheep and cattle. He also claimed one of Lyttelton's coal mines, had the miners arrested, and confiscated the stocks of coal, before setting the mine on fire.

He was again summoned by the Privy Council who tried to reason with him. Lyttelton complained to the Star Chamber and Lord Dudley was heavily fined for rioting and cattle rustling. He attempted to revenge Gilbert Lyttelton by blocking the election of his relative Edward Littleton. This resulted in two of Gilbert Lyttelton's sons, Stephen and John, attacking Lord Dudley and his retainers.

In 1597, Lord Dudley put his brother John, as a candidate in an election, in an attempt to stop the election of Sir Edward Littleton, of Pillaton Hall, near Penkridge. Lord Dudley ensured that there would be a blank return from his father-in-law Thomas Whorwood, ensuring that Littleton would loose. Bills were filed against Lord Dudley and Thomas Whorwood in the Star Chamber, but that parliament was nearly at an end, so no action was taken. The scandal ensured that Lord Dudley could have no further parliamentary career.

Lord Dudley was patron of group of actors, known as Lord Dudley's players, who had a performing bear. The company was led by Francis Coffyn and Laurence Bradshaw, and in 1595 Lord Dudley set up a warrant to allow the company to travel and perform, but soon revoked the license in favour of a different group. Because of his unbalanced behaviour, he had widespread notoriety and ensured the financial ruin of his family. He was the last Sutton to bear the Dudley title.

Lord Dudley died on the 23rd June, 1643 and was buried in St Edmund's Church, Dudley. His legitimate son, Ferdinando, died of smallpox before his father’s death. He had an only child, a daughter, Frances, who married Humble Ward. His father, William Ward, jeweller to Queen Henrietta Maria, and a wealthy goldsmith, paid Lord Dudley's debts and Frances Ward inherited the estates, becoming Baroness Dudley.

Humble Ward became Lord Ward of Birmingham in 1644. He was High Sheriff of Staffordshire in 1658.

Humble Ward and Frances had eight children:

Lord Ward, born in 1614, died on the 14th October, 1670 and his son, Edward, became the 2nd Baron Ward. Lord Ward’s wife, Frances, died on the 11th August, 1697.