His long career at The Record began in 1924 as a stringer covering local sports. He became a full-time sports writer in 1926 and then began covering local Prohibition era politics.[4] In 1927, he and another reporter uncovered a scandal involving a new sewer system in Lodi Township, New Jersey, which resulted in a senator being expelled from the New Jersey Senate.[7] In October 1931 he covered the opening of the George Washington Bridge.[8]
In 1931 he began writing his six-day-a-week editorial column called "Simeon Stylites", named after Saint Simeon Stylites, a 5th-century ascetic who lived on top of a pillar for 39 years. Each column was exactly 85 lines long and he wrote about 12,000 of them until he retired in 1972, the year after he won the Pulitzer Prize. In 1972, Rutgers University Press published a compilation of 112 of Caldwell's "Simeon Stylites" as In the Record: the Simeon Stylites Columns of William A. Caldwell (1972).[4][9]