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 Rh Scotland became thereby free. "Dear Lord Hailes was on the side of liberty," Johnson wrote to Boswell. He would have loved him still more for the tenderness of heart which, unlike so many of his brethren, he showed on the Bench. "When called to pass sentence of death he addressed the unfortunate convicts in a pathetic, dignified strain of piety and commiseration that made a deep impression on the audience." Many of the old judges, as is shown by the stories recorded of them, were in criminal trials little better than ruffians in ermine. If "robes and furred gowns hide all," in many a case they had far more cruelty to cover than the unfortunate prisoner had been guilty of who was sent to the gallows. Lord Hailes, with all his kindness, was by no means faultless as a judge. He too often allowed his pedantry to override his good sense. This failing in his friend, Boswell took off in his comic poem The Court of Session Garland:

According to Dr. Robert Chambers "a story was told of his once making a serious objection to a law-paper, and in consequence to the whole suit, on account of the word justice being thus spelt." Lord Braxfield, one of the ruffian judges, but a man of strong mind, "hearing him praised as a good judge, said, in his vulgar way, 'Him! he knows nothing but the nooks of a cause.' He was not without his crotchets. One day when he sat as President, he reprimanded a lawyer very sharply for making a ludicrous application of some text in the Gospels or Epistles. 'Sir,' said he, 'you may take liberties with the Old Testament, but I will not suffer you to meddle with the New.'"

As an historian he had considerable merits. Johnson revised the proof-sheets of his Annals of Scotland, and found them "a new mode of history in our language." "They are very exact," he added, "but they contain mere dry particulars. They are to be considered as a Dictionary. You know such things are there, and may be looked at when you please." Gibbon praised him as "a diligent collector, and an accurate critic;" but he complained that when he came to criticise "the two invidious chapters" in the Decline and Fall, "he scrutinized each separate passage with the