It is said that he once laid a wager with three other courtiers to swim from the Palace of Westminster to London Bridge, but the Queen forbade the match.

[3] The Queen, to help him in his financial difficulties, made him bow-bearer of Malvern Chase, and is said to have given him a valuable estate in Suffolk; but when he went to the place and saw the distress of the widow of the former owner, he begged to have the property transferred to her.

Strict economy and a period of retirement enabled him to pay his debts, and a wealthy marriage in 1598 (see below) greatly improved his position.

[2] The central portion of the house at Westwood, which after the Civil War became the residence of the family, was Pakington's work.

His right to alter the road being questioned, he impetuously had the embankments cut through, and the waters of his lake streamed over the country and coloured the Severn for miles.

[6][7] In November 1598, Pakington married Dorothy (died 1639), daughter of Ambrose Smith (Queen Elizabeth's silkman), and widow of Benedict Barnham.

It was the unpleasant duty of the Attorney General, Francis Bacon (who had married Lady Pakington's daughter, Alice Barnham), to give an opinion against his mother-in-law.