Holland, Sir Robert born c.1283. Baron Robert Holland senior held moderately extensive estates in his county and played an active part in its government, but his son's career was to be altogether more exceptional. Through his friendship with Thomas, earl of Lancaster, Edward II's cousin and the most powerful of his earls, he rose from the middle ranks of the gentry into the upper ranks of the baronage. Their connection probably began in 1298, when Holland served Lancaster as his vallettus on the Falkirk campaign. By 1305 he had been knighted.

From 1300, if not before, Holland began to receive a steady stream of lands from Lancaster, amounting eventually to some twenty-five manors worth perhaps £550 per annum. Lancaster was also responsible for his marriage, which took place about 1308 and led to still greater gains. His wife was Maud (d. 1349), one of the two daughters and coheirs of Alan de la Zouche, a prominent Leicestershire magnate, who brought to her husband, on Zouche's death in 1314, the greater part of her father's lands, worth nearly £720 a year. It was probably in consequence of this great accession of landed wealth that Holland was summoned to parliament for the first time in July 1314. At the height of his career his whole estate, including his patrimony, was probably worth rather more than £1300 a year.

Robert and Maud had 13 children:

Joane Holland born c. 1305 and died 1340. She married John Radcliffe

Margery Holland born c.1308

Sir Robert Holland born c. 1312 and died on 16th March 1372/73, who succeeded to his father's title and estates in 1335 and resided at Thorpe Waterville in Northamptonshire

Sir Thomas Holland

Sir Otho Holland born c. 1316 and died on 3rd September 1369 followed Thomas into military service;

John Holland born c.1318

Maud Holland born c. 1319 and married Thomas Swinnerton

Alan Holland born c. 1320 and died in 1339 followed Thomas into military service;

Elizabeth Holland born c. 1320

Margaret Holland born c. 1322. She married John de la Warr and did in 1349

Jane Holland born c. 1326

Eleanor Holland born c. 1327 and died in 1341

Elizabeth Holland born c. 1328

In return for all this Holland became Lancaster's chief agent and confidant. According to the Brut chronicle, ‘He truste more oppon him than oppon eny man alyve’ (Brut: England, 216). Chronicles and records suggest that he exercised a general supervision over all Lancaster's affairs: directing his estate officials, receiving dubiously acquired lands to which the earl wished to bar legal claims, acting as Lancaster's intermediary with the king, and supporting him in his political and military ventures. He joined in the pursuit of Piers Gaveston in 1312 and served Lancaster in Scotland in 1318. He also served the king, acting for three periods as justice of Chester and holding the usual range of local commissions. It was to the king that Holland turned during the great crisis of 1321–2, when Lancaster rebelled against Edward. This was not the result of any long-standing arrangement with Edward, for Holland had played a leading part in Lancaster's actions against the Despensers in July 1321 and had begun to raise troops for him in the revolt that followed in the winter of 1321–2. But in early March 1322, when Lancaster was retreating through the north midlands before the royal army, Holland crossed over to Edward. His treachery cost Lancaster the campaign and ultimately his life, and Holland his reputation and his freedom. His motive in deserting his lord was obvious: to save his own life in what looked likely to be—and indeed became—a military catastrophe. He may have calculated that in the event of defeat his own position as Lancaster's henchman would make him more vulnerable than his lord, whose blood and ancestry might have been expected (too optimistically as it turned out) to protect him.

For the next five years Holland remained the king's captive, and only in December 1327, a year after the old reign had ended in a revolution, did Edward III order his release and the return of his lands. His restoration was short-lived. On 15th October 1328 he was murdered in Borehamwood, near Elstree, in Hertfordshire, probably by a group of Lancastrian partisans and possibly with the connivance of Henry, Earl of Lancaster, Thomas's brother. He was probably buried at the Greyfriars' Church, Preston, Lancashire. The bulk of his lands descended to his eldest son, another Robert, but it was his second son, Thomas Holland, Earl of Kent, who refounded the family's fortunes.

Holland's linkage with the most powerful noble of his generation, and the scale of his consequent enrichment, made his career in some respects sui generis. In another way, however, it typified one of the main routes to social advancement in the middle ages: through service in the following of a great man.