Barrow worked for two newspapers in Des Moines, IA, before moving east in 1890. He formed a partnership with baseball concessioner Harry Stevens, and they got the scoreboard and pop concessions at the Pirates' Exposition Park. In 1894 Barrow became manager and GM at Wheeling, WV (International League). In 1895 he acquired the Paterson, NJ franchise in the Atlantic League, signed Honus Wagner, and served as president of the circuit from 1897 to 1899.
He then purchased a part interest of the Toronto (International League) club, became its manager, and won a pennant in 1902. The Detroit Tigers then made him their manager, but he resigned during 1904 following a dispute with the GM. When two unsuccessful years of managing in the minors followed, Barrow left baseball. Barrow returned in 1910 as president of the Eastern League.
He was named manager of the Boston Red Sox in 1918 and immediately led them to the World Championship. That season, after much prodding by Harry Hooper, Barrow finally acknowledged Babe Ruth's prowess as a hitter by increasingly working the ace pitcher into the lineup as an outfielder. The Red Sox sold Ruth to the Yankees in 1920, and at the close of the season, Barrow became the Yankee GM. In 1921-23, the Yankees won their first three pennants.
Barrow, who possessed an explosive temper, once challenged the Babe to a fight. He exercised strict discipline as manager and executive. He treated ballplayers in the typical fashion of the day, like property. Stories abound about the contract squabbles Barrow had with players. Almost always, Barrrow won these contract discussions. Barrow met his match with the young Joe DiMaggio. After his first year in New York, Joe D. was involved in a much publicized contract squabble with Barrow. DiMaggio had a secret weapon on his side, none other than Ty Cobb. Cobb, who had a residence in California, befriended Dimaggio, and became an advisor to the "Yankee Clipper." Everytime Barrow sent another copy of a contract to DiMaggio, saying that this would be the last offer, Cobb would look at the contract, laugh and tell Joe to send it back, unsigned! Eventually, Joe got his money, much to the shagrin of Barrow.
Maybe the best example of Barrow's ruthlessness in dealing with players happened when Lou Gehrig was first diagnosed with ALS in 1939. Barrow coldly informed Lou's wife Eleanor that Lou "should look for another line of work" since he was no longer of any use to the Yanks. Eleanor Gehrig never forgave the "old bastard" for the cold way he treated her beloved Lou, and rightly so.
In 1937 and 1941, he was named TSN Major League Executive of the Year. When the Yankees were sold to Larry McPhail, Dan Topping, and Del Webb in 1945, Barrow became chairman of the board, but he retired two years later. He was elected to the Hall of Fame by the Committee on Baseball Veterans in 1953, the year he died.