Introducing the all-time Yankees fantasy showdown

There are three very important things to know about me:

I like baseball.

I like history.

I have far too much time on my hands.

And so now I stand at the confluence of those three personal tidbits, about to embark on an ambitious, perhaps foolhardy, but hopefully fun journey to answer a seemingly impossible question: Of all the great teams in Yankees franchise history, which one reigns supreme?

And just how do I intend to do that, you might ask? Am I so brazen to think the answer lies in my own opinion and analysis?

Please, friend. I would never presume. I do, however, have at my disposal Google Sheets and Out of the Park Baseball 21, one of the premier baseball simulation games on the market. I aim to put them to good use over the next several weeks.

Here’s the basic idea: create a tournament bracket consisting of 32 teams and use OOTP’s historical exhibition mode to simulate seven-game series between them, until only one is left standing.

Choosing the teams is pretty simple. The 27 World Series-winning teams get an automatic bid, but that still leaves five spots to fill. I’ve decided to give the 2020 team a slot, as they’re not doing much of anything these days and it’d be fun to see how the simulation rates them against their heavy-hitting forebears.

To round out the other four spots, I’ve decided to pit eight World Series also-rans against each other in play-in matchups, based on era, giving them a second shot at glory. The 2003 team will go toe-to-toe with the 2001 squad to see who gains entry into the tournament, for example. The other battles are 1921 vs. 1926; 1955 vs. 1957; and 1964 vs. 1976.

The 27 title winners were ranked by regular season winning percentage and seeded accordingly. The top four – 1927’s Murderer’s Row, 1998, 1939 and 1961 – earned no. 1 seeds and were assigned a bracket using a random number generator. The no. 2 seeds were then also assigned a bracket using the same random number generator, and so on down the line.

The play-in winners were all assigned a no. 8 seed, regardless of their regular season winning percentage. And, just for fun, I gave the 2020 squad a no. 5 seed.

Perhaps it’d be easier to just show you the bracket? Notice there’s a tab for the wildcard round and one for the championship bracket, so you can follow along as it gets updated. (Also, the “regions” are all named after a Yankee legend.)

So with the preamble concluded, let’s get to the play-in round!

2001 vs. 2003

These two teams were only separated by a single season, but for some reason, it feels to me like they’re from different eras. There was a lot of overlap, of course: Derek Jeter, Bernie Williams and Jorge Posada were in both lineups and Andy Pettitte, Mike Mussina, Roger Clemens and Mariano Rivera anchored both pitching staffs. But 2001 was the last hurrah for ‘90s mainstays Paul O’Neill, Scott Brosius, and Tino Martinez (though he’d return for a season in 2005). The 2003 team was more star-laden, featuring Jason Giambi and Hideki Matsui.

Photo credit should read STAN HONDA/AFP via Getty Images

Each, though, produced thrilling October moments before ultimately falling in the World Series.

In this series, the 2001 team came out on top four games to two, buoyed by phenomenal starting pitching performances by Pettitte, Mussina and Clemens, who combined to throw 31.2 innings at a 0.85 ERA, striking out 39 batters against just nine walks. Tino Martinez led the way offensively, slashing .370/.370/.741 with three home runs and nine RBI on his way to a series MVP award.

They’ll move on to face Mickey Mantle, Roger Maris and the rest of the 1961 Yanks in the Round of 32.

1955 vs. 1957

You’d assume two teams featuring Mantle and Yogi Berra in their primes would be evenly matched, but after dropping the first game 6-4, the 1957 squad rattled off four straight wins to cruise to victory. Mickey and Yogi played well for the 1955 squad, but the supporting cast for ’57 was just better, including Elston Howard slashing .333/.333/.524 and Bobby Richardson going .294/.381/.529.

It also didn’t hurt that the ’57 Mantle was otherworldly, slashing .591/.640/.955 on his way to MVP honors.

Next up for them is the Joe DiMaggio-led 1939 team.

1964 vs. 1976

This play-in matchup was the only one that featured two distinctly different eras. The Mantle Yanks took one last gasp for greatness in 1964, but fell short, losing the World Series to the St. Louis Cardinals in seven games. The ’76 team, on the other hand, represented a rebirth at the end of a gloomy decade that followed the ’64 squad’s defeat.

Photo by Vincent Riehl/NY Daily News Archive via Getty Images

This contest didn’t disappoint. After falling behind 3-1 in the series, Thurman Munson’s boys pulled off an epic comeback, ripping off three straight wins to take the series 4-3. Centerfielder Mickey Rivers led the way offensively, hitting .333/.344/.633 with two home runs and seven RBI, to garner MVP honors.

They’ll hope to ride that wave of momentum into their Round of 32 series against the 1998 team.

1921 vs. 1926

The 1921 squad holds a rare distinction in this tournament field as the only team to play before the Yankees had their first taste of World Series glory. The inexperience, ahem, showed, as the ’26 team skated by them en route to a 4-0 series sweep. While both teams had Babe Ruth, the ’21 squad was without Lou Gehrig. The Babe that showed up for the ’26 team was also just better than his ’21 counterpart, hitting .364/.562/.909 with a pair of homers and four RBI. He was the MVP.

Next up for them is their nearly identical twin, the 1927 Yankees.

Stay tuned over the next few weeks for new installments, as the tournament gets under way in earnest. The goal will be to handle the first-round matchups for each bracket separately and hopefully go slightly more in depth on the game details for each.

Until then.