Billings' role as "first friend" was assessed by many observers at the time and since. Ted Sorensen called him "an admirer — almost a fawning admirer — of his friend." Arthur Schlesinger thought Billings "used to glare at me when we occasionally encountered each other in the company of JFK, and for a time I took this rather personally. Soon I discovered that he glared with equal suspicion at anyone whose friendship with JFK postdated his own." Another said: "Members of the president's staff thought of him as a 'handy old piece of furniture.'"