A first baseman, Pipp played in Major League Baseball (MLB) for the Detroit Tigers, New York Yankees, and Cincinnati Reds between 1913 and 1928.

Although he is considered to be one of the best power hitters of the dead ball era,[1] Pipp is now best remembered as the man who lost his starting role as the Yankees' first baseman to Gehrig on June 2, 1925, after experiencing a headache.

[1] In 1912, Pipp made his debut in professional baseball with the Kalamazoo Celery Pickers of the Class D level Southern Michigan League.

Pipp attempted to hold out from the Tigers, demanding a portion of the purchase price, and threatened to return to college.

[1] After playing 12 games for Detroit, batting .161, the Tigers reassigned Pipp to the Providence Grays of the Class AA International League.

He committed seven errors in 14 games for Providence, and was demoted to the Scranton Miners of the Class B New York State League, where he only batted .220.

[1][7] In January 1915, Jacob Ruppert and Tillinghast L'Hommedieu Huston agreed to purchase the New York Yankees of the American League.

As part of the agreement, the other team owners in the American League agreed to help the Yankees restock their system with prospects.

[7] On February 4, 1915, the Tigers sold Pipp and outfielder Hugh High to the Yankees, receiving $5,000 for each player ($151,000 in current dollar terms).

[1] The Yankees moved to strengthen their team after the 1919 season, adding Ruth and fellow outfielder Bob Meusel and third baseman Joe Dugan.

Led by their strong lineup and additions to the pitching staff, such as Waite Hoyt, the Yankees finished in second place in 1920.

Pipp said this resulted in reduced tension among the Yankees, to which he attributed their improved play from that point forward.

[13] Pipp had a strong 1923 season, but injured his right ankle while stepping down from a train in Boston late in the year.

Before their game against the Washington Senators, Huggins replaced Pipp in the Yankees' lineup with Gehrig, and benched second baseman Aaron Ward and catcher Wally Schang as well.

The streak started the previous day, as on June 1 Gehrig entered the game as a pinch hitter, substituting for shortstop Wanninger.

[20][21] According to the most popular version of the story, Pipp showed up at Yankee Stadium that day with a severe headache, and asked the team's trainer for two aspirin.

"[7][8][22] According to The Pride of the Yankees, the 1942 film about Gehrig's life, Pipp asked out of the game because he was experiencing double vision from being hit in the head two days prior.

[7] By 1953, Pipp reported to The New York Times that he was taken out of the lineup due to being hit in the head by a pitch thrown by Charlie Caldwell during batting practice.

Other sources suggest Yankee manager Miller Huggins may have actually benched Pipp and other veterans in order to "shake up" the slumping lineup.

[25] Ruth had returned to the Yankees' lineup on June 1, the day before Pipp, Ward, and Schang were benched.

Despite Ruth's return and the strong play of Gehrig, who batted .295 with 20 home runs and 68 RBIs,[7][18] the Yankees finished in seventh place.

Pipp was hospitalized for a week after being hit in the head by Caldwell on July 2, and he played sparingly during the remainder of the season.

[7] After retiring, Pipp invested in the stock market, but lost his wealth in the Wall Street Crash of 1929.

[24] During World War II, Pipp worked at the Willow Run manufacturing complex in Ypsilanti, building B-24 bombers.

[1][35] Pipp and his wife, Nora,[24] had four children:[7] three sons (Walter, Tom, and Wally Jr.) and a daughter (Dorothy).

After suffering a number of strokes, Pipp moved to a nursing home in Grand Rapids in September 1963.