Career in the north
Clifford made a natural ally for King Henry, and soon became one of his most trusted men in the north. Summerson suggests that Henry had little choice in restoring Clifford to his traditional regional position, as Northern England had been firmly Yorkist for over 20 years, first under the Nevilles and then under Gloucester. The latter had made Yorkshire his power base. Clifford, already loyal to Lancaster and then Tudor, was an obvious choice to act as the King's man, and Henry gradually increased Clifford's power. On 2 May 1486 Clifford received the stewardship of the Lordship of Middleham and bailiwick of the Honour of Richmond. The former had been one of Richard of Gloucester's most important headquarters. After Richard took the throne, he granted it to Sir John Conyers, one of Gloucester's closest advisers; both Middleham and Richmond had been Neville strongholds before that. Conyers seems to have been placed in Clifford's custody around this time, although relations between the two men seem to have improved: Clifford later jointly shared in a £1,000 bond to the King for Conyers's good behaviour. In October 1486 Clifford sat on a commission to "levy for the King, all profits arising from the King's manors and lands in the counties of Westmorland and Cumberland, the lordship of Penrith and the forest of Inglewood" in expectation of an invasion by Scotland.
The city of York jealously guarded its liberties, and traditionally rejected all interference from the outside unless it was perceived as absolutely warranted. This resistance troubled Clifford throughout his career. During the Yorkist rebellion of 1487, which attempted to place Lambert Simnel on the throne (as a pretender for Edward IV's second son, Richard of Shrewsbury) Clifford was responsible for guarding the city. He reinforced the garrison with 200 of his men at arms; when the rebel army passed close by, Clifford followed it to Braham. He attempted to engage it on 10 June, but was beaten off. He camped in Tadcaster overnight, where word was brought to him that a small force of rebels, led by Lords Scrope of Masham and of Bolton had launched an assault on Bootham Bar. This forced Clifford to withdraw back to York and face the rebels on 13 June. The subsequent encounter was not an unqualified success, notes Summerson; Clifford was defeated in a scuffle outside the gates, and lost all his baggage. The military historian Philip A. Haigh writes that Clifford was "utterly disgraced" and R. W. Hoyle describes his efforts as a "fiasco". The city scribes "laconically recorded the disastrous outcome", writes Anthony Goodman, and emphasised how the King's man in the north "had signally failed" to contain the rising.
Meanwhile, the King's army under John de Vere, Earl of Oxford, had won a decisive victory over the rebels at the Battle of Stoke 16 June 1487. Clifford was again given responsibility for the safety of York, and he claimed "captenship" over the city, an assertion the city rejected. In 1488 Clifford and Lady Anne both joined the city's Corpus Christi Guild. This does not seem to have restored Clifford in the eyes of the city officialdom, as the following year they again refused him entry, claiming that his intentions threatened the city's liberties. This may well have been prescient, suggests Summerson, as in 1513 Clifford attempted to claim the city's troops for his own army. In 1489 the townspeople, "denyed the entrie of the Lords Clifford and othre, that in nowise noon othre gentilman of what degreor condiconhe he of be suffred to enter this the Kyngs Chaumbre and so all to be excludet and noon to have reule bot the Maiour, Aldermen and the Shireffs". The city's statement came just before rebellion again broke out in Yorkshire, this time against heavy taxes. The commons overran the city and refused to allow Clifford or the sheriff, Marmaduke Constable entry. Instead, the citizens not only allowed the rebels to enter, they provided them a degree of military assistance. The medievalist David Grummitt comments that the city's reluctance to allow Clifford either office or military assistance is in stark contrast to the fervour with which they served "our ful gode and gracious lorde the duc of Gloucestre" as both Duke and King.
Clifford was in London in 1494 when he and the King's second son, Prince Henry, among others, were made Knights of the Bath. Clifford spent much of the remainder of the decade on service in the north. Although he never held office on the border, he led a major campaign in 1497, besieging and capturing Norham Castle from the Scots. Clifford was probably a member of the Council of the North around the turn of the century. This body was under the nominal leadership of Prince Arthur and managed by the Archbishop of York, Thomas Savage. Clifford's lordship of the north, posits Summerson, was reciprocal: Henry extended royal power in the region by strengthening Clifford, and likewise, Clifford strengthened and augmented his own position through royal service.
Clifford, although a figure of political and social influence, only ever had regional interests. His approach to his estates was generally positive, suggests Summerson. Clifford regularly travelled between Westmorland and Yorkshire (visiting manors "where no Clifford had been seen for a quarter of a century") and took the opportunity to rebuild and repair castles and other properties as he did. These he funded with traditional feudal dues, such as offices, wardships and marriages that were within his purview. His determined augmentation of his estates occasionally led to summonses before the royal council for enclosing land. Conversely, Clifford attempted to build good relations with his tenants and neighbours through financial generosity and hospitality, such as in 1521, when he held a "great Christmas" at Brough Castle.
On occasion, Clifford made the enmity of his neighbours as a direct result of his royal service. For example, it was often to the Crown's advantage that, where possible, it influenced civic elections in favour of royal candidates. A particularly important such office was that of the city recorder. In the early years of Henry's reign the administration of York, as the capital of the north, keenly interested the King. Its regional position, combined with a history of Yorkist loyalism, made it, the scholar James Lee suggests, a "touchstone for loyalty to Henry". The King attempted to impose his own man, but the city council disagreed. Clifford then attempted to intercede for the King, but to no avail, and in the end, a compromise candidate, John Vavasour, was elected. Summerson notes that Clifford's attempts to insert himself into local politics were "not always well-received". Summerson highlights Clifford's declaration in 1486 to the Mayor and Common Council that he intended "to mynistre as myn auncistres haith done here to fore in all thinges that accordith to my dewtie". In response, York's officials "firmly" informed Clifford that he had no such duty as his ancestors had never wielded such authority. Clifford also attempted, unsuccessfully, to influence the civic celebrations the city organised for the King's first visit to York later the same year. He wished, says Lee, to show the King the degree to which he was in control now that he had been returned to his family's traditional position; he was told by Vavasour that the city would do as it saw fit.
In 1487 the Earl of Oxford had been granted the wardship and marriage of the 17-year-old Elizabeth Greystoke, granddaughter and sole heiress of Ralph, Baron Greystoke. Oxford soon sold the rights (worth nearly £300 per annum) to Clifford. Within a short time, though, Elizabeth was taken from Clifford's custody ("without leave asking, and not without peril to his person") by Thomas, Lord Dacre. By 1491, relations between the two men had deteriorated to the extent that the King personally prosecuted them both in the Star Chamber for rioting; they were each fined £20. King Henry was more likely to have been concerned, in cases such as these, with bending his tenants-in-chief to his political will than the revenue these forfeits added to his Exchequer. Hicks has suggested that this behaviour made Clifford less trustworthy in Henry's eyes as a crown agent. In 1496 the Captain of Carlisle, Henry Wyatt, wrote to the King expressing, as Agnes Conway calls it, his "poor opinion" of Clifford. Wyatt considered Clifford's wife, Lady Anne St John, to be a more able administrator than her husband, whom he considered inefficient, and told the King so plainly.
Clifford's success at improving his finances eventually placed him in the top third of the English nobility and enabled him to successfully create new connections and strengthen existing ones. This he achieved through both marriage alliances with, and retaining among, the local gentry. Clifford was also a major patron to local abbeys, monasteries and priories. To Bolton Priory, for example, he donated a manuscript now known as A Treatise of Natural Philosophy in Old French. Other houses included Gisborough, Mount Grace and Shap; Mount Grace was particularly favoured. Clifford was a regular correspondent with the heads of other houses, including Byland, Carlisle, Furness, Holmcultram and St. Mary's, York. His extensive patronage did not always bring him success in his political negotiations with them. In 1518, for example, the Dean of York, Brian Higton wrote to Clifford explaining why he had refused to accept Clifford's favoured nominee as parish priest of Conisbrough Church:Where ye dide of laite presente your clerk unto the church of Conesburgh of your patronege, surely I cane nott (of my conscience) admytte hym to itt, fore his connyng is mervyllus slendure. I haue scyne few prestis so symple lernede in my life. If itt please you to commande some of your lernede chapplens to oppoise hym in your presence, I dowte not butte ye shall perceyue the truth. And fore the lakk of his lernynge (Which is manifesteo) I do putte hym bakk, ande fore noyne oder cause, nor at no mannys desire or motlon.