If you have any interest in the history of baseball and the Yankees, you’ve probably wondered what the best Yankees team of all-time might be. However, unless someone invents a real time machine anytime soon, there’s no real way to figure that out. Even then, just dropping the 1927 Yankees into 1998 for a series against that Bronx Bombers team probably wouldn’t provide any real answers, as the further we get into history, the better the training methods get, and the more the older squads would be at a physical
disadvantage, no matter how good the actual careers of the likes of Babe Ruth, Mickey Mantle, and company were.
The closest we can probably get is simulations, and a perfect one for baseball history is Out of the Park Baseball. I’ve posted in the past about various experiments I’ve done on OOTP, from rewriting Yankees’ history to turning Eduardo Núñez into a superhuman.
Since we’ll never be able to do this in real life, I decided to put every single Yankees’ team from 1903 through 2024 in one league. (The latest edition of the game, OOTP 26, came out before the 2025 campaign, so we don’t really have an accurate representation of what the 2025 Yankees ended up like in it.) I turned off trades to try and keep the roster as accurate as possible, although teams could still release players and pick others up, and the game auto-created some fictional players to help fill in with injuries. However other than that, the rosters mostly stayed the same as they did in real life. With that in mind, let’s see what happened.
Finishing with a 115-47 record and first place in the regular season: the 1938 Yankees. In real life, the ‘38 Yankees won 99 games and their third consecutive World Series, but probably wouldn’t be in the upper tier of teams considered the franchise’s all-time best. However in this simulation, they were led by a 11.2 WAR season from Joe DiMaggio, who hit .377 with 57 home runs (for what it’s worth, Joltin’ Joe never topped 46 dingers in a single season). The team also had four other 50+ home run hitters in the lineup, including Lou Gehrig, who in real life had a really-good-but-not-excellent season, as he was probably just starting to feel the effects of ALS.
As you can see with one team having five 50+ home run hitters, this simulation ended up having an absolutely wild offensive environment. The co-home run leaders were 1921 Babe Ruth (59 in real life) and 1927 Babe Ruth (60 in real life), who each hit an insane 86, as six players would’ve obliterated the actual single-season home run record of 73.
Despite that, there were some sterling pitching performances. The 1934 version of Lefty Gomez led the league in ERA at 2.52 in 221 innings. That might not sound that insane, but with the offensive environment, it was actually a 210 ERA+. Somewhat surprisingly, the pitching WAR leader was actually 1962 Al Downing, who threw just one major-league inning in real life that year. However in this, the 21-year old was remarkable at limiting homers in the environment, allowing just nine in over 200 innings.
George Mogridge (who once threw a no-hitter in our world) racked up a 4-22 record, as the 1918 Yankees had to rely on him for 32 starts despite a 6.50 ERA. Meanwhile, pour one out for 1904’s Walter Clarkson, who issued 199 walks in 154.1 innings with a 16.62 ERA.
One of the more surprising things is that neither of the normally considered best Yankees’ teams ever, 1927 and 1998, made our league’s playoffs. The 1998 team went 95-67, but in a league with over 100 teams, that was only good enough for 19th. Meanwhile, despite the aforementioned 86 Ruth homers, the 1927 squad went just 88-74, as their pitching mostly struggled.
The biggest overachievers compared to real life was probably the 1910 Highlanders. In real life, they were a solid team who finished second in the AL, but in this game, they were two games better than the ‘98 Yankees, winning 97 games.
The eight-team playoff field ended up being made out of 1938, 1942, 1931, 1939, 1963, 1947, 1962, and 1934, who won a one-game playoff over 1941 to get in. Those teams all won 90+ games in real life, and many of them won the World Series, but I can’t say I would’ve anticipated a couple of them getting in.
Having gone 106-56 in the regular season, the 1931 Yankees ended up coming from the No. 3 seed to win the All-Yankees World Series, besting 1938 in seven games.
The 1931 Babe Ruth was named series MVP after slugging four home runs, including one in Game 7.
The funniest part of that is that the real 1931 Yankees missed out on the World Series after finishing 13.5 games back of that year’s Philadelphia Athletics in the AL pennant race. Yet apparently, they won out in this simulation. Technology is weird sometimes.
