Outland was born in Hesper, Kansas to Thomas Outland and Mahala Outland into a Quaker family who settled in Kansas from Indiana around 1860 during the Bleeding Kansas period as part of a larger Quaker immigration to Kansas in support of the Free State cause. He grew up mostly in Johnson County, Kansas in the towns of Lexington, Kansas and Edgerton, Kansas though. He was a member of the first football team at Penn College in Oskaloosa, Iowa in 1891. Outland captained the team in 1892, scoring 32 of the team's 36 points. After starring in football and baseball at the University of Kansas in 1895 and 1896, Outland went to Philadelphia to complete his medical education at the University of Pennsylvania Medical School. There he became one of the few men ever to win All-American football honors as both lineman and the backfield player. He was picked by Walter Camp as a first-team All-American in 1897, as a tackle. In 1898, he was selected again, this time as a halfback. He was captain of the 1898 Pennsylvania team and was voted "Most Popular Man" at the University of Pennsylvania. Outland worked his way through college and spent his last two summers as a companion to rich young men who were alcoholics. To keep them away from alcohol, Outland took them on camping trips in the Wyoming mountains.
Coaching career
Franklin and Marshall
In 1900, Outland coached the football team at Franklin & Marshall College in Lancaster, Pennsylvania for one season. His team produced a record of 4–5. He was the 11th coach of the program that began in 1887.
Outland also coached at Washburn University in Topeka, Kansas. He was the ninth head football coach for Washburn and he held that position for two seasons, from 1904 until 1905. His overall coaching record at Washburn was 14–5. Outland's 1905 season ended with an experimental game with Fairmount University where a new rule forcing the offense to earn a first down in three plays instead of four was in effect. The experiment was considered a failure.
Later life
After receiving his medical degree, Outland returned to Kansas in 1900 where he set up his medical practice first in Lawrence, Kansas which led to his hiring as the head football coach of the University of Kansas. On January 28, 1902 Outland married Ethel Arnett Grimes in her hometown of Dana, Indiana. He then moved his practice to Topeka, Kansas in 1904 in order to coach the Washburn University football team. In 1906 Outland moved his family to Kansas City, Kansas where he joined the very first staff of the brand new Trinity-Lutheran hospital in Kansas City, Missouri as a general practicing surgeon. Later, in about 1916, while still on staff with Trinity-Lutheran hospital he moved his family across state lines to Kansas City, Missouri where he lived until his retirement. During his time as a practicing surgeon he extensively used his own plane, often flying with famous Kansas City early aviation pioneer pilot John Kerr "Tex" LaGrone, to visit patients in rural areas and far flung towns, being the first doctor in the Kansas City area to do so. While practicing medicine in the Kansas City region, Dr. Outland served for many years on the athletic board of the University of Kansas alongside other notable KU alumni, Dr. James Naismith and Dr. Forrest "Phog" Allen amongst others. Dr. Outland also served as a referee for college football games, including the 1907 Iowa State - Nebraska game in which he rendered the decision that negated an Iowa State field goal and preserved a 10-9 Nebraska victory. Upon his retirement he moved to Laguna Beach, California. He also served as a major in the United States Army Medical Corps during World War I.
Outland was the founder of the Kansas Relays, having obtained the inspiration for that event at Penn, when as a student, he saw the Penn Relays just getting under way. For many years he held the post of honorary referee of the Kansas events.
Outland Trophy
Outland conceived the idea of the Outland Trophy because of his belief that interior lineman were not given enough recognition in college football. The trophy is the third oldest college football trophy. Selection of the winner is made by the Football Writers Association of America.
Death
Outland suffered a stroke in March 1947 and died at his home in Laguna Beach, California two weeks later on March 24, 1947. He was survived by his wife, Ethel, daughter Mrs. Mary McDougall of New Orleans, Louisiana, and son John Grimes Outland of Dallas, Texas. Outland was laid to rest in Maple Grove Cemetery in Wichita, Kansas near his parents' graves.
