Brought to the Guildhall in 1834, this portrait of John Hales was previously displayed at the Coventry Free Grammar School, to whom it was given in 1704 by the widow of a descendant of John Hales. Although the portrait depicts John Hales as the kindly benefactor, with the school he founded shown in the background of the painting, Hales seems to have been an unpopular individual in his own lifetime. Around the time of the Reformation, Hales had profited from the availability of cheap land and property from the many dispossessed religious houses of Coventry, his purchases including the Benedictine Priory estate in 1544, and Whitefriars monastry circa 1543, making the latter his chief residence, which he renamed "Hales Place". The means by which Hales accumulated his great wealth and property portfolio was criticized by contemporaries, who regarded such blatant profiteering as disrespectful and blasphemous.