I've previously written a post about the murder of Sir Robert Holland in October 1328, and another about his daughter Isabelle, mistress of John de Warenne, earl of Surrey (d. 1347). Here's one about Robert himself, a knight of Lancashire whose grandchildren were the older half-siblings of King Richard II.
Robert's family came originally from the village of Upholland in Lancashire, and in the thirteenth and fourteenth centuries, the name was spelt Holand, Holande, Holond, Holaund(e), Hoyland, Hoylaund, etc. Robert's father was also called Sir Robert Holland, and the older Robert was the eldest of the six sons of Thurstan Holland, who was himself the son of yet another Robert Holland.  This Robert and his son Thurstan, our Robert's great-grandfather and grandfather, were imprisoned in 1241 after setting fire to a house belonging to the rector of Wigan.
Our Robert's mother, Elizabeth, was the third and youngest daughter, and co-heir, of Sir William Samlesbury, who married Avina Notton and died in c. 1256, leaving their three daughters Margery, Cecily and Elizabeth as his heirs. Elizabeth and Sir Robert Holland Senior were certainly already married by September 1276 and probably a good few years before that. Robert Senior is assumed to have died c. 1304, while Elizabeth was still alive in 1313/14. The date of birth of Robert and Elizabeth's eldest son and heir, our Robert, is not recorded but was probably sometime near the start of the 1270s; his father settled a tenement on him in Pemberton and Orrell in 1292, suggesting he was at least twenty-one then and may have recently turned twenty-one. In the late 1310s and early 1320s, a 'Simon de Holand' (d. 1325) was associated with Robert, who gave him a plot of land in Lancashire, and there was also a 'Richard de Holand, knight' who joined the Contrariant rebellion of 1321/22 with Robert. There's an entry in the Final Concords for Lancashire in October 1321 regarding 'Richard son of Robert de Holand, plaintiff'.  As the sons of our Robert Holland were still children in 1321, this would appear to mean that Richard was a son of Robert Holland Sr (d. c. 1304) and therefore our Robert's brother. Robert certainly had a younger brother named William, who died in the late 1310s or early 1320s and whose son and heir was named Robert, and there are also references in the chancery rolls in the 1330s and 1340s to another son of William's called Thurstan.
J.R. Maddicott has pointed out that Robert Holland's origins were not quite as humble as some fourteenth-century chroniclers, notably the Brut and Henry Knighton - who wrote that the earl of Lancaster raised Robert 'from nothing' - claimed.  C. Moor's Knights of Edward I (vol. 2, p. 233) states that our Robert was active as a knight and a keeper of the peace in Lancashire as early as 1287, but surely that's his father of the same name. As so often happens when father and son had the same name, it's difficult, or even impossible, to distingush between them, especially when the son reached an age where he became active as a knight and soldier. It was possibly the younger Robert, rather than his father, who was appointed to 'choose 2,000 footmen' in Lancashire in June 1300, and who was appointed as a commissioner also in Lancashire in May 1303. 
As early as September 1300, the younger Robert Holland was already associated with Edward I's nephew Thomas of Lancaster, earl of Lancaster and Leicester, who was then in his early twenties (my belief is that Thomas was born on or around 29 December 1277). On 18 September 1300, Edward I ordered his escheator beyond Trent 'not to intermeddle further with the lands that Robert de Holand had of the gift of Thomas, earl of Lancaster, tenant in chief, in Beltesford, which the escheator has taken into the king's hands because Robert entered them without his licence.'  This is an early indication of Robert's close relationship with Thomas of Lancaster, which lasted for over twenty years. In March 1316, Thomas founded a chantry in Worcester to pray for the souls of his royal parents Edmund of Lancaster, earl of Lancaster and Leicester (d. 1296) and Blanche of Artois, dowager queen of Navarre (d. 1302), on the anniversaries of their deaths. The monks were also to pray on the anniversaries of two people currently still alive, after their deaths: Thomas himself, and Sir Robert Holland. Thomas didn't ask for prayers for his wife Alice de Lacy or his younger brother Henry or Henry's children or anyone else, just Robert Holland, an indication of Robert's importance in his life. J.R. Maddicott has called Robert Thomas of Lancaster's 'companion and friend, estate steward, political agent, and general factotum', and states that their 'close friendship...ran at a deeper level than that of a mere business partnership'.  There are numerous instances in the chancery rolls of Earl Thomas granting manors to Robert and his wife Maud, and their heirs.
Edward II appointed Robert Holland to the important position of justice of Chester on 28 August 1307, at the beginning of his reign. Robert held the office until late 1311, was replaced, but then re-appointed a few weeks later.  At the beginning of the reign, and until c. late 1308 or early 1309, Thomas of Lancaster was closely associated with his cousin the king, and the two men were on excellent terms. Things went badly wrong, however, and for reasons that are unclear, Thomas began to move into opposition to his cousin. The two royal men came to detest and fear each other, especially after Thomas's involvement in the death of Piers Gaveston in June 1312. A jousting tournament was held in Dunstable, Bedfordshire in the spring of 1309, which a large number of the English earls and barons used as a cover to meet and express their disgruntlement with Edward II's governance. Thomas, earl of Lancaster, and Sir Robert Holland were among those present.  Edward replaced Robert as justice of Chester with Payn Tibetot in late 1311, but in January 1312 spoke of Robert's 'good service' to him and re-appointed him as justice of Chester, being aggrieved with Tibetot, who had 'treated with contempt the king's mandate directed to him'. 
The king sent a letter to Sir Robert Holland on 20 November 1311, stating that 'we are very joyous and pleased about the good news we have heard concerning the improvement in our dear cousin and faithful subject Thomas, earl of Lancaster, that he will soon be able to ride in comfort. And we send you word and dearly pray that, as soon as he is comfortable and able to ride without hurt to his body, you should ask him to be so good as to hasten to us at our parliament'.  It was as though Robert was the earl's deputy and spokesman, and sometime between 1319 and early 1322, Robert and Earl Thomas sent virtually identical letters to Edward II regarding the manor of Farnley in Yorkshire (the only real difference I can see between the two letters is that Robert's opening salutation to Edward was far more deferential).  Sometime before 13 May 1306, Robert Holland married Maud la Zouche, co-heir to her father Alan (d. 1314) with her older sister Ellen or Elena.  Maud brought Robert a good few manors in several counties in the Midlands and south of England, and it's surely reasonable to assume that Thomas of Lancaster had something to do with arranging such a favourable marriage for his most trusted adherent and associate.
During the Contrariant rebellion of 1321/22, however, Robert abandoned Thomas of Lancaster, and on 4 March 1322 was ordered to 'come to the king with all speed with horses and arms, in order to set out with the king against his contrariants'. On the same day, Edward II granted Robert a safe-conduct for 'coming to the king by his command and about to go against the contrariants'. Robert Holland's switching sides was surely connected to the fact that one of his and Maud la Zouche's daughters, unnamed, had been taken into captivity in the Tower of London on 26 February 1322, along with Aline de Braose and John Mowbray (b. 1310), wife and son of John, Lord Mowbray (b. 1286): '...conducting by the king's command to the Tower of London Aline, the wife of John de Moubray, and the son of the said John, also the daughter of Robert de Holand...'.  According to the very pro-Lancastrian author of the Brut chronicle, when Thomas of Lancaster heard about Robert's defection, he groaned 'how might Robert Holonde fynde in his hert me to bitraye, sithens that y have lovede him so miche?' Thomas supposedly went on to say that he had 'made [Robert] hie fram lowe', i.e. high from low. 
Despite his taking armed men to the king, on 12 March 1322 Edward had all of Robert's goods and his lands in Lancashire, Northamptonshire, Nottinghamshire, Derbyshire, Lincolnshire, Leicestershire, Yorkshire, Northumberland, Shropshire and Staffordshire taken into his own hands. Robert also owned 'houses called the houses of Viene in the city of London' which were confiscated, and were possibly the same dwellings which in 1325 were called the 'king's houses in the parish of St Nicholas in the Shambles of London, sometime of Robert de Holand'. On 23 June 1322, Edward stated that Robert was 'charged with being an adherent of Thomas, sometime earl of Lancaster' - Thomas had been executed at his own castle of Pontefract in Yorkshire three months earlier, on 22 March - and had 'surrendered to the king's will'.  After Robert's and Thomas of Lancaster's downfall, one William de Leveseye petitioned the king, stating that the earl and Robert ('Sire Rob't de Holande') had imprisoned him in Pontefract Castle in Yorkshire for over a year 'because he was in the company of Sir...', then the petition is sadly torn and the name is missing. 
During the Contrariant rebellion, Robert had sacked several Leicestershire towns including Loughborough which belonged to Hugh Despenser the Elder, in the company of, among others, William Trussell, who in October and November 1326 would pronounce the death sentence on both Hugh Despensers. According to a petition, Robert and his associates chased the 'poor people' of Loughborough out of their homes and they did not dare to return for three months. On 1 October 1323, Edward II ordered the sheriff of Leicestershire not to outlaw Robert for his failure to appear in court to answer for the sacking of Loughborough, because he was in prison at the king's order and was therefore unable to attend.  Robert was originally imprisoned in Warwick Castle in 1322, and on 23 July 1326 was moved from there to Northampton Castle. A few months later, early in Edward III's reign, he was pardoned for escaping from prison in Northampton 'when confined there by the late king's order', though his lands were then still officially in the king's hands, and on 12 June 1327 his manors in Yorkshire were given into the custody of one Thomas Deyvill. While he was imprisoned in Warwick Castle, shortly after 4 November 1325, royal officials questioned Robert regarding the assignment of dower to his brother William's widow Joan.  The date of Robert's escape from Northampton Castle was not recorded, though the window of opportunity for him to do so was only quite small given that he was moved there after 23 July 1326 and that Queen Isabella and her invasion force, who freed the imprisoned Contrariants, arrived in England on 24 September 1326.
In my post about Robert Holland and Maud la Zouche's daughter Isabelle, also linked above, I listed their other children; they had at least four sons and five daughters. Their first son and heir was another Robert (d. 1373), who was said to be sixteen on 1 December 1328 and seventeen or 'seventeen and more' in early January 1329, placing his date of birth around 1311/12 (sadly, there is no extant proof of age confirming the exact date).  Their second son Thomas, whose name probably indicates that Thomas, earl of Lancaster, was his godfather, raised the Holland family high when he married Edward I's granddaughter Joan of Kent, later countess of Kent and Lady Wake in her own right (though when Thomas married her, her younger brother John, earl of Kent, was still alive). Thomas Holland died in late December 1360, and a few months later his widow married Edward III's eldest son the prince of Wales and became the mother of Richard II in January 1367. Thomas Holland's children were, therefore, the older half-siblings of the king of England. Robert Holland's grandson John Holland (c. 1353-1400) married Edward III's granddaughter Elizabeth of Lancaster and was later made earl of Huntingdon and duke of Exeter by Richard II, while John's older brother Thomas Holland (1350/51-1397), earl of Kent, married the earl of Arundel's daughter Alice and their children included the duchesses of York and Clarence and the countesses of March and Salisbury. In just a couple of generations, the Holland family rose from comparative obscurity in the north to become one of the foremost families in the land.
1) J.R. Maddicott, 'Thomas of Lancaster and Sir Robert Holland: A Study in Noble Patronage', English Historical Review, 86 (1971), p. 450.
2) Complete Peerage, vol. 6, pp. 528-31; Maddicott, 'Thomas of Lancaster and Sir Robert Holland', pp. 450-51; CCR 1318-23, pp. 210, 571; CFR 1319-27, p. 168; Calendar of Inquisitions Miscellaneous 1308-48, no. 735; Calendar of Inquisitions Post Mortem 1317-27, nos. 497, 567, 707; A History of the County of Lancaster, vol. 3, pp. 394-5; Final Concords for Lancashire, part 2, 1307-1377, no. 127.
3) Maddicott, 'Thomas of Lancaster and Sir Robert Holland', p. 450.
4) CCR 1296-1302, p. 401; CPR 1301-7, p. 191.
5) CCR 1296-1302, p. 365.
6) CPR 1313-17, p. 441; Maddicott, 'Thomas of Lancaster and Sir Robert Holland', p. 462.
7) CFR 1307-19, pp. 2, 5, 10; CPR 1307-13, pp. 38, 411, 427.
8) Collectanea Topographica et Genealogica, ed. F. Madden, B. Bandinel and J.G. Nichols, vol. 4, p. 67.
9) CPR 1307-13, pp. 411-12, 427; CCR 1307-13, p. 396.
10) Cited in G.O. Sayles, The Functions of the Medieval Parliament of England, vol. 1, p. 302; The National Archives SC 1/45/221.
11) TNA SC 8/234/11687 and 11689.
12) Feet of Fines, Berkshire, CP 25/1/9/38, no. 10, dated 13 May 1306, talks of 'Robert de Holond and Maud his wife' when the manor of Denford was given to them with remainder to Maud's father Alan la Zouche.
13) CCR 1318-23, p. 525; CPR 1321-24, pp. 75, 77.
14) The Brut or the Chronicles of England, ed. F.W.D. Brie, part 1, pp. 216-17.
15) CFR 1319-27, p. 109; CPR 1321-24, pp. 137, 337; CPR 1324-27, p. 158.
16) The National Archives SC 8/58/2872.
17) CPR 1321-24, pp. 167, 309, 387; CCR 1323-27, p. 24.
18) CCR 1323-27, p. 592; CPR 1327-30, p. 17; CFR 1327-27, p. 46; CIPM 1317-27, no. 707.
19) TNA SC 8/57/2806; SC 8/57/2807A and 2807B; Brut, ed. Brie, p. 257.
20) CFR 1327-37, p. 105.
21) CCR 1327-30, pp. 348, 491; CIPM 1327-36, no. 156; CIPM 1347-52, no. 199.