Born in a covered wagon in Springfield, Illinois, Barrow worked as a journalist and soap salesman before entering the business of baseball by selling concessions at games.

After managing the Tigers in 1903 and 1904 and returning to the minor leagues, Barrow became disenchanted with baseball, and left the game to operate a hotel.

After a seven-year tenure, Barrow managed the Red Sox from 1918 through 1920, leading the team to victory in the 1918 World Series.

When Red Sox owner Harry Frazee began to sell his star players, Barrow joined the Yankees.

During his quarter-century as their baseball operations chief, the Yankees won 14 AL pennants and 10 World Series titles.

[2] Barrow worked as mailing clerk for the Des Moines News in 1887, receiving a promotion to circulation manager within a year.

[3] Barrow then bought the Paterson Silk Weavers of the Class-A Atlantic League, managing them for the rest of the 1896 season.

[1] Barrow discovered Honus Wagner throwing lumps of coal at a railroad station in Pennsylvania, and signed him to his first professional contract.

[1][4][8] Barrow sold Wagner to the Louisville Colonels of the National League (NL) for $2,100 the next year ($76,910 in current dollar terms).

[1] With the money earned from the sale of the Richmond movie theater, Barrow purchased a one-quarter share of the Toronto Maple Leafs of the Class-A Eastern League in 1900 from Arthur Irwin,[3] and served as the team's manager.

[1] The Eastern League hired Barrow as its president the next year, giving him an annual salary of $7,500 ($245,250 in current dollar terms).

[13] When the league's owners voted to cut his pay to $2,500 after the 1917 season ($59,455 in current dollar terms), Barrow resigned.

As the team lost many of its better players during World War I, Barrow encouraged owner Harry Frazee to purchase Stuffy McInnis, Wally Schang, Bullet Joe Bush, and Amos Strunk from the Philadelphia Athletics for $75,000 ($1,519,248 in current dollar terms).

He traded Dutch Leonard, Duffy Lewis, and Ernie Shore to the New York Yankees, obtaining Ray Caldwell, Slim Love, Frank Gilhooley, Roxy Walters, and cash.

[17] The Red Sox struggled in 1919, finishing sixth in the AL.[18] Frazee sold Ruth to the Yankees after the season, against Barrow's warnings.

[19] To date, Barrow is the only manager to win a World Series without previously playing in organized baseball, whether in the minors or majors.

After the 1920 season, Barrow resigned from the Red Sox to become the business manager of the Yankees, replacing the deceased Harry Sparrow.

[25] The Yankees sought to develop their own players, rather than buying them from other teams, especially after the investment of $100,000 ($1,754,023 in current dollar terms) in Lyn Lary and Jimmie Reese in 1927.

[26] However, Weiss and Bill Essick convinced Barrow to approve the purchase of Joe DiMaggio from the Pacific Coast League.

[27] When Huggins died in 1929, Barrow chose Bob Shawkey to replace him as manager, passing over Ruth, who wanted the opportunity to become a player-manager.

[33] His body was kept at Campbell's Funeral Home[33] and interred in Kensico Cemetery in Valhalla, Westchester County, New York.

[35] Barrow was also the first to require the playing of "The Star-Spangled Banner", the United States' national anthem, before every game, not only on holidays.