The Yankees - Red Sox rivalry is one of the oldest, most famous and fiercest rivalries in American professional sports. For over 100 years, Major League Baseball's Boston Red Sox and New York Yankees of the American League have been intense rivals. The rivalry is sometimes so polarizing that it is often a heated taboo subject, like religion or politics, in the Northeastern United States.

Since the inception of the wild card team and an added Division Series, the American League East rivals have squared off in the American League Championship Series three times, with the Yankees winning twice in 1999 and 2003 and the Sox winning in 2004. In addition, the teams have twice met in the last regular-season series of a season to decide the league title, in 1903 (when the Red Sox won) and 1949 (when the Yankees won). The teams also finished tied for first in 1978, when the Yankees won a high-profile one-game playoff for the division title.

The 1978 division race is memorable for the Red Sox having held a 14-game lead over the Yankees more than halfway through the season. Since before the start of the American Revolution, Boston and New York have shared an intense rivalry as cities. For more than a century afterwards, Boston was arguably the educational, cultural, artistic, and economic power in the United States.

Boston's location as the closest American port to Europe and its concentration of elite schools and manufacturing hubs helped maintain this image for several decades. During this time period, New York was often looked down upon as the upstart, over-populated, dirty cousin to aristocratic and clean Boston. New York's economic power soon outpaced Boston's in the 1800s due to its rapid population growth and terminus of the Erie Canal, along with massive growth in the manufacturing, shipping, insurance and financial services businesses.

By the start of the 20th century this dynamic had completely shifted as New York had become the focus of American capitalism (especially on Wall Street), and the change was reflected in the new national pastime. The Red Sox were one of the most successful teams in baseball at the turn of the 20th century and through the following two decades. They won the inaugural World Series in 1903 (as the Boston Americans; they changed their name to the Red Sox in 1908) and four more between 1912 and 1918.

During this period, the Yankees were often called the Highlanders, in reference to playing their games in the Washington Heights neighborhood of Manhattan. Although physically located on a hilltop, the Highlanders routinely finished near the bottom of the standings. The one notable exception came in 1904, when the Highlanders, led by pitcher Jack Chesbro who won a record 41 games, met the Boston Americans in the final game of the season to decide the AL pennant.

Chesbro threw a wild pitch and Boston won the pennant, but there was no World Series that year as the Giants refused to play. That would be the last time in a hundred years that the Red Sox would defeat the Yankees in a title-deciding game. In 1916, Harry Frazee purchased the Red Sox on credit for $500,000.

Though the team won the World Series in 1918, Frazee was hard-pressed to pay off the loans he accrued by purchasing the team and by producing Broadway shows. After the Red Sox finished sixth in the American League in 1919, Frazee sold several players, including pitcher-turned-outfielder Babe Ruth, to the Yankees. Frazee received $125,000 and a loan of $300,000—secured on Fenway Park, the Red Sox' home stadium—for Ruth.

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