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Founded by St. Gilbert, about the year 1130, at Sempringham, Gilbert's native place, where he was then parish priest. His wish originally had been to found a monastery, but finding this impossible, he gave a rule of life to the seven young women whom as children he had taught at Sempringham, and built for them a convent and cloister to the north of his parish church. He received the support of his bishop, Alexander of Lincoln, and in a year's time the seven virgins of Sempringham made their profession. Gilbert seems to have been determined to copy the Cistercians as much as possible. At the suggestion of William, Abbot of Rievaulx, he instituted lay sisters to attend to the daily wants of the nuns, and soon added a company of lay brothers to do the rougher work in the farms and fields. These he recruited from among the poorest serfs of his parish and estates. For eight years the little community at Sempringham continued to flourish, and it was not till about 1139 that the infant order was increased by another foundation. Alexander of Lincoln gave to the nuns of Sempringham the island of Haverholm, near Sleaford, in Lincolnshire, the site of one of his castles destroyed in the contest between King Stephen and his barons. Alexander's deed of gift makes it clear that the nuns had by this time adopted the Cistercian rule "as far as the weakness of their sex allowed". The fame of Sempringham soon spread far and wide through that part of England, and the convent sent out several colonies to people new foundations. In 1148 Gilbert travelled to Cîteaux in burgundy to ask the Cistercian abbots there assembled in chapter to take charge of his order. This they refused to do, declining to undertake the government of women, and so Gilbert returned to England, determined to add to each of his convents a community of canons regular, who were to act as chaplains and spiritual directors to the nuns. To these he gave the Rule of St. Augustine. Each Gilbertine house now practically consisted of four communities, one of nuns, one of canons, one of lay sisters, and one of lay brothers. The popularity of the order was considerable, and for two years after Gilbert's return from France he was continually founding new houses on lands granted him by the nobles and prelates. These houses, with the exception of Watton and Malton, which were in Yorkshire, were situated in Lincolnshire, in the low-lying country of the fens. Thirteen houses were founded in St. Gilbert's life, four of which were for men only.

The habit of the Gilbertine canons consisted of a black tunic reaching to the ankles, covered with a white cloak and hood, which were lined with lamb's wool. The nuns were in white, and during the winter months were allowed to wear in choir a tippet of sheepskin and a black cap lined with white wool. The scapular was worn both by the canons and the nuns. The whole order was ruled by the "master", or prior general, who was not Prior of Sempringham, but was called "Prior of All". His authority was absolute, and the year formed for him a continual round of visitations to the various houses. He appointed to the chief offices, received the profession of novices, affixed his seal to all charters, etc.. and gave or withheld his consent regarding sales, transfers, and the like. He was to be chosen by the general chapter, which could depose him if necessary. This general chapter assembled once a year, at Sempringham, on the rogation days , and was attended by the prior, cellarer, and prioress of each house.

St. Gilbert, soon finding the work of visitations too arduous, ordained that certain canons and nuns should assist him. These also appeared at the general chapter. A " priest of confession" was chosen to visit each house and to act as confessor extraordinary. A Gilbertine monastery had only one church: this was divided unevenly by a wall, the main part of the building being for the nuns, the lesser part, to the south, for the canons. These had access to the nuns' part only for the celebration of Mass. The nunnery lay to the north, the dwellings of the canons were usually to the south. At Sempingham itself, and at Watton, we find them at some distance to the north-east. The number of canons to be attached to each nunnery was fixed by St. Gilbert at seven. The chief difficulty Gilbert experienced was the government of the lay brothers. They were mostly rough and untamed spirits who needed the control and guidance of a firm man, and it would have been surprising had there been no cases of insubordination and scandal among them. Two instances especially claim our attention. The first is related by St. Ælred, Abbot of Rievaulx, and gives us an unpleasant story of a girl at Watton Priory who had been sent there to be brought up by the nuns ; the second was an open revolt, for a time successful, of some of the lay brothers at Sempringham.

From their foundation till the dissolution of the monasteries the Crown showed great favour to the Gilbertines. They were the only purely English order and owed allegiance to no foreign superiors as did the Cluniacs and Cistercians. All the Gilbertine houses were situated in England, except two which were in Westmeath, Ireland. Notwithstanding the liberal charters granted by Henry II and his successors, the order had fallen into great poverty by the end of the fifteenth century. Henry VI exempted all its houses from payments of every kind — an exemption which could not and did not bind his successors. Heavy sums had occasionally to be paid to the Roman Curia, and expenses were incurred in suits against the real or pretended encroachments of the bishops. By the time of the Dissolution there were twenty-six houses. They fared no better than the other monasteries, and no resistance whatever was made by the last Master of Sempringham, Robert Holgate, Bishop of Llandaff, a great favourite at court, who was promoted in 1545 to the Archbishopric of York. The Gilbertines are described as surrendering "of their own free will ", each of the nuns and canons receiving "a reasonable yearly pension". Only four of their houses were ranked among the greater monasteries as having an income above £200 a year, and as the order appears to have preserved to the end the plainness and simplicity in church plate and vestments enjoined by St. Gilbert, the Crown did not reap a rich harvest by its suppression.

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