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An Alternate History of the Yankees: the 1990s

Using the game Out of the Park Baseball 21, we’ve been going back through time and rewriting Yankees and baseball history. The computer is controlling all teams, and all real life transactions have been turned off. Therefore, it’s possible the likes of Babe Ruth, Mickey Mantle, Reggie Jackson, and Derek Jeter will never end up in pinstripes, while other notable names end up as Yankee stars. Here’s where you can read parts one, two, threefourfivesix, seveneight, and nine. Let’s see what happens next as we begin the 1980s.

National Baseball Hall of Fame Induction Ceremony Photo by Mark Cunningham/MLB Photos via Getty Images

Where we last left off, the Yankees had failed to win a World Series in the 1980s. That came despite the team taking full advantage of the relatively new creation of free agency. The team brought in a host of big names in the 80s, headlined by third baseman Mike Schmidt. However, none of them could lead the Yanks to their first title since 1971.

Now we go to the 1990s. Can the Yankees get back to the promised land, much as they did in real life, or will the simulation version of the franchise end up in the doldrums?

1990: 97-65, 3rd in AL, 7 GB, Team WAR Leader: C Carlton Fisk (6.5)

The Yankees have an excellent season behind a turn-back-the-clock performance from a 42-year old Fisk. They just got stuck in the best division in baseball and finish a ways behind the 104-win Brewers.

Said Milwaukee team would fall in the World Series, getting swept by a Padres team led by Cal Ripken and Nolan Ryan. Meanwhile in the draft, a young catcher named Jorge Posada is selected by the Angels, and pitcher Andy Pettitte goes to the Brewers.

1991: 91-71, T-3rd in AL, 7.5 GB, Team WAR Leader: 1B Wally Joyner (5.9)

The AL East is a little bit worse, but so are the Yankees, leading to a similar finish as the year before. The Brewers again topped it and came out of the AL, but they again lost in the World Series, this time to the Cubs.

In the draft, the Orioles use their first round pick to select a shortstop named Derek Jeter.

1992: 77-85, 5th in AL East, 22 GB, Team WAR Leader: SP Bill Swift (5.1)

The Yankees make a managerial change, getting rid of John Lytle and promoting bench coach Bill Knapek. They also bring in outfielder Darryl Strawberry, a four-time All-Star with the Padres and Astros, on a one-year deal. He couldn’t help much as the Yankees slid way down to fifth in the division.

Meanwhile, the Brewers finally climb the mountain and win the World Series, avenging their loss to the Cubs.

1993: 83-78, 3rd in AL East, 24 GB, Team WAR Leader: SS Craig Grebeck (5.6)

The Yankees make a quick managerial change, getting rid of Knapek after one season and bringing in Glenn Goya. They also bring in catcher Darren Daulton on a six-year deal.

Elsewhere in baseball, two expansion teams are added to the NL in the Colorado Rockies and Florida Marlins. The Yankees don’t end up losing any important names in the ensuing expansion draft.

The Yankees move up a couple places, but they still fall well short of the Brewers. However, it’s the Dodgers that take home the title, beating the A’s in the World Series. Shortstop Alex Rodriguez goes first overall to the Angels in the draft

1994: 56-106, 4th in AL East, 38 GB, Team WAR Leader: SP Bill Swift (2.4)

Another big change comes to baseball as MLB creates a third division in each league and adds a round and Wild Cards to the playoffs.

In New York, the Yankees are getting very quick with the trigger finger. Goya gets just one season and is replaced by Jerry Pomeroy. However, everything comes crashing down around him as the Yankees put up a 106-loss season. They somehow only finished with the fourth worst record as the Orioles, Marlins, and Rockies are all truly putrid. (The Marlins went 37-125!) The Brewers may not be in the AL East anymore, but they continue their dominant period, beating the Expos in the World Series.

The Yankees use their bad season to get an outfielder named Carlos Beltran in the ensuing draft.

1995: 41-121, 5th in AL East, 55 GB, Team WAR Leader: 1B Don Mattingly (1.7)

You won’t believe this, but the Yankees made a managerial change going into ‘95. After that 106-loss season, Pomeroy is out and Jerry Leak is in. To help him, the Yankees sign several big names to one-year deals including Tony Gwynn, Rickey Henderson, and a veteran first baseman named Don Mattingly.

Unfortunately, they can’t help the Yankees avoid a truly awful season. The pitching is especially bad, allowing 1270 runs on the season. The “best” Yankees starter was Jim Deshaies, who had a 6.78 ERA. Somehow, this team was better than the Rockies by a game.

The Dodgers beat the Athletics in the World Series, and in the draft, the Yankees select third baseman Victor Martinez.

1996: 65-97, 4th in AL East, 26 GB, Team WAR Leader: CF Dave Martinez (4.6)

Henderson is brought back, while Bobby Bonilla is also signed for one year. Thankfully, they didn’t give Bonilla a long term deal that they will have to continue paying well into the future. The team improves by a pretty big 24 wins. It’s just that a 24-win improvement on 41 only takes you to 65 and the fifth worst record in the league. The use another high pick to take pitcher Johan Santana.

In the playoffs, Oakland avenges their loss from the previous season and beats the Reds for the title.

1997: 78-84, 3rd in AL East, 4 GB, Team WAR Leader: 1B Will Clark (4.6)

Three-time All-Star with the Mets and Angels, Will Clark, is signed to a four-year deal. A 20-year old Beltran also makes his debut and shows promising signs for the future. The team take another step forward, and nearly make the playoffs in an incredibly weak AL East. The pitching is still an issue, so they spend another first round pick on a pitcher, taking Rick Ankiel.

Phillies star Mark McGwire sets a new single-season home run record, slugging 60. The Pirates, with a Randy Johnson and David Cone-led pitching staff, take the World Series crown.

1998: 81-81, T-3rd in AL East, 24 GB, Team WAR Leader: CF Ray Lankford (4.4)

The league expands once again, and the Yankees get a new division mate in the Tampa Bay Devil Rays, while the Arizona Diamondbacks join the NL.

The Yankees take another step forward, but still fall way short of an Orioles teams that features the likes of Jeter and Nomar Garciapara. Said Baltimore team would get upset by the Wild Card Angels, featuring Mike Mussina and Rodriguez, who then go all the way to a World Series championship.

The Yankees add Mark Buehrle in the draft as they continue to build back towards contention.

1999: 75-87, 3rd in AL, 25 GB, Team WAR Leader: CF Carlos Beltran (5.8)

In the offseason, the Yankees manage to add Ken Griffey Jr. on just a one-year deal, and Jimmy Key for two years. Despite all that, the Yankees dropped way back out of contention. One good sign is that Beltran appears to be on his way to becoming a star, putting up a very impressive season as just a 22-year old. They go on to add Cliff Lee and Rocco Baldelli in the ensuing draft.

The Angels go back-to-back, losing just four games on their way to a title.

Yankees 90s Award Winners

  • Ricardo Rincon: Reliever of the Year 1997
  • Mike Schmidt: Hall of Fame Class of 1995 (Inducted as a Brewer)