The journalist and newspaper editor and executive, was born at 311 Newport Road, Middlesbrough, He was educated at Middlesbrough high school. He began his career as a journalist with the Northern Echo and remained a working journalist until a few months before his death, following a remarkably long and distinguished career during which he worked closely with three of the most powerful British newspaper barons of the twentieth century-the second Viscount Rothermere, Lord Beaverbrook, and Rupert Murdoch.
Pickering moved to Fleet Street, first to the Daily Mirror as a sub-editor and then to the Daily Mail where by 1939 he was chief sub-editor, a senior and demanding position requiring sure news judgement and technical proficiency. During World war II, . Pickering became so close to Ike that he sometimes attended his regular meetings with King George VI when Eisenhower reported on progress after D-day.
After the war, and a brief stint in Manchester, Pickering returned to Fleet Street in 1947 as managing editor of the Daily Mail. It was then that Lord Beaverbrook, offered him a job, and in 1951 he became second-in-command to Arthur Christiansen, editor of the Daily Express, the Mail's fiercest rival. The partnership of the capricious and demanding Beaverbrook and Christiansen, the supreme journalistic professional, had driven the Express to a sale of more than four million; for ambitious journalists it was the most glamorous and exciting newspaper in Fleet Street.
In 1956 Christiansen suffered a heart attack when he was staying with Beaverbrook in the south of France. He was moved aside and in 1957 Pickering became editor of the Daily Express. However, although he was successful, Beaverbrook decided that the paper again needed an editor with the flair and panache of Christiansen. On Christmas eve 1962 Pickering was fired. It was a characteristically brutal act by Beaverbrook, who further humiliated Pickering by putting him in charge of Farming Express.
Pickering was rescued from journalistic oblivion by Hugh Cudlipp, chairman of the Mirror Group and in 1964 he became editorial director of the Daily Mirror, Sunday Mirror and The People. His 'retirement' in 1977 did not last long. When Pickering was editor of the Daily Express, Sir Keith Murdoch, the Australian newspaper tycoon, had asked his old friend Beaverbrook if he could find work experience for his son Rupert, who had just graduated at Oxford. Beaverbrook put him on the sub-editors' table. 'Take care of him, Pick, you never know where he might end up', he said. Pickering did indeed take good care of the young Murdoch and taught him the rudiments of journalism. Murdoch did not forget his mentor and Pickering remained with Murdoch and News International, owner of the Times titles, until his death.
He had a unique relationship with Winston Churchill. Once or twice a week after the Second World War, Churchill would phone Pickering at the Daily Express. The conversation never varied:

Good evening, Mr Pickering.

Good evening, Mr Churchill.

You have my information?

I do.

Pickering would then read out the closing prices of certain stocks on Wall Street.