Charles Caldwell was born August 2, 1901, in Bristol, on the border of Virginia and Tennessee, and then the family moved to Yonkers and resided on Lawrence Street. He began his meteoric rise to football fame as fullback on the Yonkers High School county champion in the early 1920’s. At Yonkers High School he was a four letter man in football, baseball, basketball and track. His major sport however, was baseball, not football. He learned his sport fundamentals at Yonkers High School under Coaches Leon Kirberger and Jimmy Lee.
In addition to pitching for Yonkers High School he was often on the mound for semi-professional teams in the area, notably the Kennedy All Star. During one of the many games he played in the Yonkers area he hit what many consider the longest home run ever hit at Pelton Field.
Following his graduation from Yonkers High School he attended Mercersburg Academy and then Princeton University, where he is remembered as one of Princeton’s greatest athletes, winning seven letters (three in football, three in baseball and one in basketball). His pitching duels with Owen Carroll, then of Holy Cross and later of American League fame, made intercollegiate baseball history and earned Caldwell a tryout with the New York Yankees. He still holds mark for the longest drive ever hit inside the baseball park. Dissatisfied with the relative inaction accorded him as a bench warming rookie he left to join the Princeton football coaching staff. He completed a three-year apprenticeship under Coach Bill Rapper and then was named coach at Williams College. In 17 years he coached 15 football teams, 14 baseball teams and 11 basketball teams and compiled and overall winning average of .588.
He was named football coach of Princeton in 1945 and in 12 years compiled a winning percentage of .694. In 1946 he was one of three coaches selected by the War Department to teach football in American-Occupied Germany. Both his 1950 and 1951 elevens rolled through undefeated seasons and each time won the Lambert Memorial Trophy, emblematic of Eastern football supremacy. In 1950 he was named “Coach of the Year” by a record number of votes in national balloting. Caldwell was named 1952 recipient of the Touchdown Club of New York’s annual award for meritorious service and outstanding contributions to football over a period of years “Previous winners of this honors included Alonzo Stagg, “Pop” Warner, Lou little, Grantland Rice, Andy Kerr, General Douglass MacArthur and Admiral William Halsey.
In 1951 he authorized “Modern Singled-Wing Football” and in 1953 he wrote “Modern Football for the Spectator”
He died on November 1, 1957, at the age of 56.