McCormick was born in Chicago to a distinguished family, and known as "Bertie" to his family because he had so many relatives named Robert. His maternal grandfather was Tribune founder and former Chicago mayor Joseph Medill. On his father's side, his great-uncle was inventor and businessman Cyrus McCormick. His elder brother Joseph Medill McCormick (known as Medill McCormick) was slated to take over the family newspaper business but was more interested in running for political office. From 1889 through 1893, he lived a lonely childhood with his parents in London where his father Robert Sanderson McCormick was a staff secretary to Robert Todd Lincoln and ambassador to the Austria-Hungary, Russia, and France. In London, Bertie attended Ludgrove School. On his return to the United States, he was sent to Groton School. In 1899, McCormick went to Yale College, where he was elected to the prestigious secret society Scroll and Key, graduating in 1903. He attended law school at Northwestern University School of Law and served as a clerk in a Chicago law firm, being admitted to the bar in 1907. The following year, he co-founded the law firm that became Kirkland & Ellis, which represented the Tribune Company. He was a partner until 1920. In 1910, he took control of the Chicago Tribune, becoming editor and publisher with his cousin, Captain Joseph Medill Patterson, in 1914, a position he held jointly until 1926 and by himself afterwards.
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