Meanwhile, Woodruff had decided to quit school.
As he recalled, This was Depression times and there was very little money in our house, so I figured if I could find some kind of job I could earn a little bit of money and help out at home. I quit school, but when I went looking for work, nobody was hiring. I was turned down everywhere. So I decided to go back to school.
In spring, when it came time for track to begin, Coach Joseph Pop Larew approached Woodruff about trying the sport. His mother agreed, since he would be getting home earlier than he had in football and could get his chores done.
The first time he ever ran in scholastic competition, Woodruff won both the 880-yard and mile runs and, before he graduated in 1935, he owned new school, Fayette County, district and state records, plus, in 1935, he broke the national school mile record with a 4:23.4 winning time.
His athletic ability caught the attention of local schools and Pitt and Ohio State were at the top of his list.
I was interested in Ohio State because Jesse Owens was there, but there were some business people in Connellsville who were also Pitt men and they got me a scholarship to Pitt. If it wasn't for that scholarship, I couldn't have made it. I was the only one from my family to go to college.
Times were tough and Woodruff struggled to get by in college.
I reported to Pitt with 25 cents in my pocket. Some people in Pittsburgh helped me get a room at the YMCA in the Hill District and I had to fight the bedbugs for sleeping space. Pitt track coach Carl Olson gave me $5 and since hamburgers were a nickel and hot beef sandwiches were 20 cents, I made that do a week.
Woodruff was only a freshman at the University of Pittsburgh in 1936 when he placed second at the National AAU meet and first at the Olympic Trials, earning a spot on the U.S. Olympic team. In one of the most exciting races in Olympic history, Woodruff became boxed in by other runners and was forced to stop running. He then came from behind to win in 1:52.9. The New York Times described the race:
He remembered the anguish of his Olympic race: Phil Edwards, the Canadian doctor, set the pace, and it was very slow. On the first lap, I was on the inside, and I was trapped. I knew that the rules of running said if I tried to break out of a trap and fouled someone, I would be disqualified. At that point, I didnt think I could win, but I had to do something.
Woodruff was a 21-year-old college freshman, an unsophisticated and, at 6-foot-3, an ungainly runner. But he was a fast thinker, and he made a quick decision.
I didnt panic, he said. I just figured if I had only one opportunity to win, this was it. Ive heard people say that I slowed down or almost stopped. I didnt almost stop. I stopped, and everyone else ran around me.
Then, with his stride of almost 10 feet (3.0 m), Woodruff ran around everyone else. He took the lead, lost it on the backstretch, but regained it on the final turn and won the gold medal.
It was another gold medal for the United States so-called Black Auxiliaries the Nazis term for the black athletes and another thorn in the side of Adolf Hitler, who greeted every white winner, but none of the blacks.
Every winner in the 1936 Olympics received an oak tree from the Black Forest of Germany, presented by the German government. John brought his home, and presented it to the city of Connellsville. It was planted at the south end of the city football stadium, where today it still stands more than 60 feet straight and tall.
During a career that was curtailed by World War II, Woodruff won one AAU (Amateur Athletic Union) title in the 800 meters in 1937 and won both the 440-yard (400 meter) and 880-yard (800 meter) IC4A titles from 1937 to 1939. Woodruff also held a share of the world 4x880-yard (800 meter) relay record while competing with the national team.
Woodruff graduated in 1939, with a major in sociology, and then earned a Masters Degree in the same field from New York University in 1941. He entered military service in 1941 as a Second Lieutenant and was discharged as a Captain in 1945. He reentered military service during the Korean War, and left in 1957 as a Lieutenant Colonel. He was the battalion commander of the 369th Artillery, later the 569 Transportation Battalion New York Army National Guard.
Woodruff also worked as a teacher in New York City, a special investigator for the New York Department of Welfare, a recreation center director for the New York City Police Athletic League, a parole officer for the state of New York, a salesperson for Schieffelin and Co. and an assistant to the Center Director for Edison Job Corps Center in New Jersey.
He passed away on October 30, 2007 at the age of 92.