Starting out in the family brewing business, Ruppert entered the 7th Regiment of the New York National Guard in 1886 at the age of 19, eventually reaching the rank of colonel.

He started as a barrel washer, working 12-hour days for $10 a week ($339 in current dollar terms),[8] and eventually became vice president and general manager of the brewery.

In January 1914, his father bought J&M Haffen Brewing Company for $700,000 ($21,293,023 in current dollar terms), intending to close the brewery down and develop the property, which was located near The Hub in The Bronx.

Ruppert and Tillinghast L'Hommedieu Huston, a former United States Army engineer and colonel, purchased the Yankees from Farrell and Devery before the 1915 season for $480,000 ($14,456,842 in current dollar terms).

After the 1917 season, Ban Johnson, president of the AL, suggested that Ruppert hire St. Louis Cardinals manager Miller Huggins to take over the same position with the Yankees.

Huston, who was in Europe at the time serving as an engineer in World War 1, disliked Huggins and wanted to hire the manager of the National League's crosstown Brooklyn Robins, Wilbert Robinson, his drinking buddy.

[15][16] The hiring of Huggins drove a wedge between the two co-owners that culminated in Huston selling his shares of the team to Ruppert in 1922.

[17][18] Ruppert and Huston purchased pitcher Carl Mays from the Boston Red Sox in 1918, in direct opposition of an order issued by Johnson.

As a result of the Yankees' increased popularity, Charles Stoneham, owner of the Giants and the Polo Grounds, raised the rent for the 1922 season.

[23] The following season, the Yankees finally beat the Giants to win their first World Series title.

The Yankees went on to dominate baseball throughout most of the 1920s and 1930s, winning three more pennants from 1926 through 1928, including the Murderers' Row team that won the 1927 World Series and repeated as champions the following year.

"[24] in 1931, Commissioner Kenesaw Mountain Landis allowed for the creation of farm systems directly operated by major league teams.

His own strength as a baseball executive – including his willingness to wheel and deal – was aided by the business skills of general manager Ed Barrow and the forceful field managing of Miller Huggins, until his sudden death at age 50 late in the 1929 season, and Joe McCarthy, beginning in 1931.

By the time of Ruppert's death, the team was well on its way to becoming the most successful in the history of Major League Baseball, and eventually in North American professional sports.

[7][30] He was survived by his brother George and his sister Amanda, and was interred in the family mausoleum at Kensico Cemetery, Valhalla, New York.

After mismanaging Ruppert's brewery, the heirs sold the Yankees to Dan Topping, Del Webb and Larry MacPhail in 1945.

[38] On December 3, 2012, Ruppert was elected to the National Baseball Hall of Fame by the new Pre-Integration Era Committee, which considers candidates (managers, umpires, executives, and players) every three years that have been identified by the Baseball Writers' Association of America (BBWAA) appointed Historical Overview Committee from the era prior to 1947.