Hugh Beeston was born in 1442, the second son to Thomas Beeston, Lord of Beeston, Cheshire. As a young man, he demonstrated his loyalty to the crown by joining the ranks of the Lancastrian army where he learned the sorry lesson of defeat at the following battles:

Bloore Heath (1459, luckily survived the disastrous rout of James Touchet, Lord Audley's army). Northampton (1460, somewhat surprised when everyone else in Lord Grey's flank laid down their weapons, so fled with the rest of the army). Mortimer's Cross (1461, another rout and a particularly unpleasant argument with Jasper Tudor on the way).  Towton (1461, actually came down with a heavy cold, so remained in York when the battle took place, which was just as well really as the Lancastrians went down to a staggering defeat). Hexham (1464, somehow got caught up in the rout of Lord Roos detachment before a single blow had been struck, thus avoiding the slaughter following the inevitable Lancastrian defeat).

Deeming it wise to leave the county for a little while, he decided to go crusading. However, as the holy land was a considerable distance away, he chose the more accessible Baltic for his adventure. Unfortunately, crusading in this area had finished some years previously, so opportunistically, he joined the forces of the Orden der Brüder vom Deutschen Haus St. Mariens in Jerusalem (also know as the Teutonic Order), for the tail end of the rather unfashionable 13 years war.

A few years later, he made his way to Burgundy and joined the retinue of Edward, Prince of Wales, in time for the invasion of the west country and the ensuing battle of Tewksbury (1471). Escaping from yet another spectacular defeat, he again departed England for an Italian sojourn. As luck would have it, he became a mercenary in the pay of Constanzo I Sforza in the jolly town of Pesaro. After some years of looting and avoiding any form of conflict (like the rest of Italy), he had made a modest fortune and returned to England.

Realising the Lancastrian game "was up", he finally swore loyalty to the newly crowned King, Richard III. Shortly thereafter, at the Battle of Bosworth Field (1485), he notably fell off his horse (which probably saved his life), just prior to Richard's final disastrous charge. Remounting and fleeing the battle, he quietly retired to Cheshire to open a brewery. Hugh disappears from the records sometime after 1520.