Red Sox History: Ranking the biggest ‘What Ifs’ in franchise history

BRONX, NY - OCTOBER 16: Pedro Martinez #45 of the Boston Red Sox pitches against the New York Yankees in the first inning during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)
BRONX, NY - OCTOBER 16: Pedro Martinez #45 of the Boston Red Sox pitches against the New York Yankees in the first inning during game 7 of the American League Championship Series on October 16, 2003 at Yankee Stadium in the Bronx, New York. (Photo by Al Bello/Getty Images)
1 of 11
Boston Red Sox Fenway Park
BOSTON, MASSACHUSETTS – OCTOBER 20: The full moon raising while the Boston Red Sox play against the Houston Astros in Game Five of the American League Championship Series at Fenway Park on October 20, 2021 in Boston, Massachusetts. (Photo by Omar Rawlings/Getty Images)

The Red Sox have some of the biggest ‘What-Ifs’ in history

It’s hard to feel too bad for Red Sox fans recently. Their team plays in the most beloved ballpark in baseball, has owners who truly care about the team and are willing to spend money, are competitive almost every year, and, oh yeah, have won four World Series titles in the last eighteen years.

Still, Red Sox history is not without its what-ifs. Whether it be a costly trade, a bad break in a critical game, or a late-season collapse. The Red Sox could have easily won a few more titles if a couple of things had gone in their favor.

When making these rankings, my one rule was to stay clear of individual players. I solely focused on team-oriented topics. So while players like Tony Conigliaro and Jimmie Foxx never reached their full potential due to injuries, they are not included on this list.

Schedule