Hastings father was Sir Leonard Hastings, who had a modest estate in Leicestershire and Gloucestershire, where the family had long been established. His mother was Alice Camoys, daughter of Elizabeth Mortimer and the 1st Baron Camoys. Elizabeth Mortimer was in turn daughter of Edmund Mortimer, 3rd Earl of March, and Philippa of Clarence, daughter of Lionel of Antwerp, a son of Edward III. Elizabeth Mortimer had also married Henry "Hotspur" Percy. Thus Hastings was second cousin to Edward IV, and to the Earl of Northumberland.
As a young man Hastings served in the household of his cousin, Richard, Duke of York. There he apparently became close to the duke's son Edward, who he was to loyally serve all his life. He fought with Edward at the Battle of Mortimer's Cross and followed him to London. After Edward was proclaimed king, Hastings was appointed Lord Chamberlain (1461). He again fought with Edward at the Battle of Towton which secured Edward's crown. Shortly after the coronation he was created Baron Hastings of Hastings, was named to a number of royal offices, and received a very large grant from the estates forfeited by Lancastrian peers. These estates were concentrated in the English Midlands. He also married Katharine Neville, sister of Warwick the Kingmaker.
Hastings followed Edward IV during Edward's exile in 1470, and returned with him in 1471. He raised a good portion of the Yorkist troops that fought at Barnet and Tewkesbury. Hastings was one of the commanders at both of those battles.
With Edward back on the throne, Hastings resumed his place as Chamberlain and his influential place at Court. When Edward died in 1483, he expected to continue on during the minority of Edward's son Edward V. However he was arrested on charges of treason by Edward's brother Richard and executed shortly afterwards, the first recorded execution at the Tower of London.
Considerable controversy surrounds the circumstances of Hastings' death. Most historians say that he was executed at most a few hours after his arrest, on June 13, 1483, while others believe he was held for a week, and possibly even had a trial of some sort. There is also disagreement regarding the truth of the accusations against him. Every agrees that he opposed, or would have opposed any efforts to displace Edward V. It is less clear whether Hastings had in fact been conspiring in some way to oppose Richard, or, if he was, whether his conduct should be construed as treason.
Hastings lands were not forfeited as is usual in the case of treason, and during the reign of Henry VII his son was allowed to succeed to his baronial title.