Osgood, nicknamed "Win", was one of the greatest college athletes of the 19th century. He was talented in many sports but is best known for his exploits as an
All-American football player. Osgood stood 5–9, weighed 173, and was an elusive runner.
Pudge Heffelfinger, the legendary All-American from
Yale University, gave this description of Osgood: "It was downright uncanny to watch him run, opponents missed him by inches. His body undulated like a snake's. He was the
Red Grange of the pioneer era." Osgood was a considered one of the top players in the early years of Big Red football. In an article on January 29, 1927,
The Sun named him to the first team of the all-time Cornell football team. Osgood also rowed on the varsity in 1890. In 1892, he was the single
scull championship of the Cornell. He left Cornell in the fall of 1892 to attend the
University of Pennsylvania, drawing controversy over whether or not he was paid to do so. In an affidavit given on October 28, 1893, he stated he "would be afforded more advantageous opportunities" for civil engineering upon graduation.
Pennsylvania At Pennsylvania, Osgood continued his exploits as a three-sport athlete, excelling at football, track and field, and wrestling. He lettered two seasons at halfback for the
Quakers under Hall of Fame coach
George Washington Woodruff. In his first year, he helped the 1893 Quakers to a 12–3 record. The team had a strong start, winning its first 11 games. During that stretch, the defense only gave up 18 points while the offense scored 305 points. But Penn lost three out of the last four games to perennial powers
Harvard,
Yale and
Princeton. At the time Penn rarely beat the "Big Three", as they were known. Osgood received widespread press in the 14–6 loss to Yale, as he scored Penn’s only touchdown in the game. In 1894, Osgood helped Penn to its first undefeated season. The 1894 squad featured one of the greatest backfields of all time, consisting of
Carl Sheldon Williams at
quarterback,
George Brooke at
fullback, and Osgood and
Alden Knipe at halfback. Osgood, Knipe and Brooke were all named to
Walter Camp's
All-American first team that year. The team was widely recognized as 1894's
football national champion. The highlight of the season was a 12–0 victory over Princeton, only Penn's second win in 30 meetings with the Tigers, and an 18–4 victory over Harvard.
Other sports Throughout his college career, Osgood participated in other sports outside of football. He took up boxing after losing a fight during a 1891 football game at the
University of Chicago, with the hopes of "evening up things if he ever met the slugger again." Around 3 years later, he would win the collegiate heavyweight boxing championship. Osgood also excelled at wrestling. He became the first collegiate athlete to win a national championship when he won the 1895 National
AAU title in the "heavyweight" class (for competitors over 158 pounds). At the time the sport was dominated by club teams. In 1894, Osgood became a letterwinner for the University of Pennsylvania's Men's Track & Field team, for the 440-yard dash and shot put. He also was a gymnast for Pennsylvania's Men's gymnastics team, a champion single scull rower, and a tennis player. With a time of 5:28, he set the 2-mile collegiate record for cycling on May 13, 1893, repeatedly breaking his own record with times of 5:08 on June 6, 1894, 4:55 on June 4, 1895, and 4:49 on the same day. ==Indianapolis light Artillery==