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An Alternative History of the Yankees: The 1900s

Let’s use video games to see how different Yankees’ history could’ve turned out.


During these baseball-less pandemic times, several of us here at Pinstripe Alley have been using the game Out of the Park Baseball as sources of content for articles.

The reason for that is that the game has an very expansive ability to mess around with. Therefore, you’ve seen us turn Eduardo Nunez into the greatest player ever, and have a tournament to determine the best ever Yankees team. There are lots of ways in the game to create interesting scenarios. One of those things you can do is replay history. So, that’s what we’re going to do.

I have used OOTP to go back to 1903, the first year the then Highlanders, now Yankees, played in New York, and have started playing through history. I am not controlling them or any other team, and all historic real life transactions have been turned off. Therefore, not only will Babe Ruth possibly not be sold by the Red Sox to the Yankees, but he might not end up with Boston at all. Things start out with the realistic rosters from 1903 with the Highlanders being managed by Clark Griffith with Jack Chesbro as the team’s star. After that, it remains to be seen what happens.

Will the Yankees still become the dominant team in baseball history? Where will various franchise legends end up? Will the Yankees in Red Sox end up becoming big rivals or will battles with another team end up becoming the marquee rivalry? Let’s find out in an alternative history of the Yankees.

1903: 71-69, 5th in AL, 20 GB, Team WAR Leader: P Jack Chesbro (6.2)

Much as they were in real life, Griffith’s first Highlanders team were .500ish and finished middle of the pack. Chesbro, Jimmy Williams, and Willie Keeler were the starts of the franchise’s first year in New York. As was the case in real life, Boston beat the Pirates in the first ever World Series.

1904: 73-81, 6th in AL, 16 GB, Team WAR Leader: P Hooks Wiltse (6.7)

I won’t compare every team to their real life counterpart, as in a few short years the roster will be wholly different and incomparable. However, the real life 1904 Highlanders played an important role in that season that the alternative history version did not.

In 1904, there was no World Series played, as the runaway NL winner Giants pulled out. The reason for that was that it appeared they would have to play the Highlanders. The Giants were not pleased that the AL put a team in New York City, and didn’t wish to acknowledge the existence of the Highlanders. As it turns out, they wouldn’t have had to deal with this possibility as the Highlanders lost the AL pennant on the final day of the season. However, the Giants stuck to their guns and didn’t play actual AL champion Boston.

In this version, that wouldn’t have ever been an issue as the Highlanders were firmly middle of the pack in the AL. The two league winners would be the same as their real life counterparts, and the Giants won in seven games.

1905: 67-87, 6th in AL, 41 GB, Team WAR Leader: P Jack Chesbro (6.3)

Despite the solid rotation combo of Chesbro and Wiltse, the Highlanders fall way behind the AL champion Athletics, who would fall to the Brooklyn Superbas in the World Series in a major upset.

1906: 72-82, 5th in AL, 31 GB, Team WAR Leader: 2B Jimmy Williams (5.6)

After three years, Griffith was replaced as manager by Ned Hanlon, who had previously managed the Superbas. However, Hanlon was replaced after 1904 and as you read above, his former team then won the title the following season. Hanlon would last just one year with the Highlanders as his team finished way back of the Cleveland Naps. The NL champion Pirates would beat Cleveland in the World Series.

1907: 57-97, 8th in AL, 45 GB, Team WAR Leader: 2B Jimmy Williams (5.1)

Jimmy Phelps took over for Hanlon, but his first year didn’t go great, as the Highlanders slid all the way to last place. New York’s pitching allowed a league worst 753 runs. Help would be seemingly be on the way as the Yankees drafted (the draft came into existence far earlier in this universe) a player named Shoeless Joe Jackson. For the second time in three years a 100+ win A’s team would fall in the World Series, this time losing to the Cubs.

1908: 62-92, 7th in AL, 31 GB, Team WAR Leader: P Hooks Wiltse (4.9)

Another losing season, but another future building block acquired by the Highlanders as they draft George Burns. In other news, the A’s finally got on the board, beating the Phillies in an all-Philadelphia World Series

1909: 69-85, 6th in AL, 35 GB, Team WAR Leader 3B Bobby Byrne (6.8)

The Highlanders made another managerial move, promoting bench coach Nick Bohler to the head job. He would last just one season after the team put up another bad season. A 19-year old Shoeless Joe made his debut and put up solid impressive numbers in 53 games. The A’s went back-to-back when they beat the Giants. Former Cardinals and Superbas manager Patsy Donovan was hired as Bohler’s replacement and a new dawn in Highlanders/Yankees baseball was on the horizon.

To wrap up this decade, here is are the best player in baseball history who ended up in a different spot than where they did in real life

  • Ty Cobb: Washington Senators
  • Walter Johnson: St. Louis Cardinals