Few pause to consider that the gate itself was once a physical threshold, the western entrance into the medieval city of Dublin, where armed men were turned back, where a guild of glovers were paid to keep watch through the night, and where, every July, a fair took place at which the only commodity on sale was ale. The gate no longer stands, but its location, at the eastern end of St. James's Street where it meets Thomas Street, marked a boundary that shaped the city's geography for centuries.

The gate's history is traceable through the Dublin Assembly Rolls, which record the city's administrative decisions in unusual detail. In 1485, Garret, the Earl of Kildare, sent horsemen against it in an attempt to enter the city; according to the Calendar of Carew Manuscripts, citizens on the walls spotted them in time and had the gates shut. By 1556 the structure had been heightened and converted into a gatehouse, with a Walter Clynton granted the adjacent ground on a forty-one-year lease in exchange for six shillings and eight pence annually, paid at Easter and Michaelmas. In 1599 the gatehouse tower was leased to the master and wardens of the company of glovers, who were required to repair it at their own expense, keep the gate open and shut as required, and maintain a watchman on the roof each night. A 1625 entry notes that the city's own works masters were to repair the gate if the glovers' lease did not already bind them to it. The gateway and its tower separated St. James's Street from Thomas Street and gave access to the Liberty to the north and St. Thomas Court beyond. It appears on John Speed's 1610 map of Dublin, labelled as James Gate. Immediately to the south stood St. James's Well, a medieval holy well; a 1620 lease records that the plot of ground between the gate and the well measured roughly 13.7 metres in length. Each year on the 25th of July, the feast day of Saint James the Apostle, a pattern and fair were held at this well. A pattern, in Irish tradition, is a gathering at a holy site involving prayer and ritual on a saint's feast day. The writer Barnaby Rich, visiting in 1610, described the fair with evident scepticism: attendees would cast water from the well backwards and forwards, over their heads and to either side, drink a draught of it, and then proceed to spend the remainder of the day drinking ale in what he called brothel-booths.

The gate itself is long gone, and the site is now occupied by the Guinness brewery complex, which has absorbed the name if not the structure. Rocque's 1756 map of Dublin and the 1886 Ordnance Survey city sheet both show how the area looked before the modern streetscape took over, and both are accessible through digitised map collections. The general location is easy enough to find on foot, at the junction where St. James's Street becomes Thomas Street, and the well's former position to the south of that point is recorded in the archaeological record even if nothing visible remains above ground.