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McCobb was born in Medford, Massachusetts to Raymond and Winifred McCobb. Both his father and mother were born in Massachusetts although neither family originated there. His father's family being from Maine and his mother's family from Ireland. His father was employed in 1920 as a Salesman in "Men's Furnishings".
McCobb enlisted in the Army as a Private on December 5, 1942 in Boston, MA. While enlisted in the Army he was attached to the Camouflage Corps of the Army Corps of Engineers. He only served in the military for a short time and was released on a medical discharge in 1943.
McCobb first came to prominence in 1948 as a design and decorating consultant for Martin Feinman’s Modernage Furniture in New York City. While employed at Modernage, McCobb met B. G. Mesberg, his later business partner in the Planner and Directional furniture lines.
His Planner Group, manufactured by Winchendon Furniture Company, was among the best selling contemporary furniture lines of the 1950s and was in continuous production from 1949 until 1964.
Other well-known furniture lines designed by McCobb include Predictor by O’Hearn Furniture, The Irwin Group by Calvin Furniture, The Connoisseur Collection by H. Sacks and Sons, The Calvin Group by Calvin Furniture, and Directional by Calvin Furniture.
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