The Black Hawks, who never iced a strong lineup while Bentley played, made a significant trade early in the 1947–48 season. They sent Max Bentley and a prospect to the Toronto Maple Leafs in exchange for five players. The trade shocked Doug. He thought about retiring following the deal but felt he could give Chicago at least one more good season. He gave them several good seasons, finished the following three seasons with 57, 66 and 52 points respectively, was named to the Second All-Star Team in 1949, and appeared in four more All-Star Games in 1948, 1949, 1950 and 1951. Chicago's "Herald American" newspaper named him the city's top hockey player of the half-century in 1950.