An Alternate History of the Yankees: the 2000s

The Yankees had a fairly uneventful 90s, failing to make the playoffs in the decade. However, those bad seasons led to a rebuild and they appear to have a decent young core. In the organization are young stars and/or highly rated prospects the likes of Carlos Beltran, Johan Santana, and others.

Now that it’s a new decade, can the Yankees continue their regeneration back into contention or will the 2000s end in disappointment? Let’s check in with the latest edition of our rewrite of history.

2000: 81-81, 2nd in AL East, 11 GB, Team WAR Leader: RF Preston Wilson (7.4)

The Yankees went a big nuts in the offseason, trading for David Justice, and signing Jeff Kent, Greg Maddux, and Jim Thome to five, five and seven-year deals respectively. Then as spring training began, they traded third baseman Randy Velarde for two-time MVP Roger Clemens.

The acquisitions were a big help on the offensive side of things, as the Yankees scored the fourth most runs in all of MLB. However, the pitching acquisitions didn’t match up, leading the Yankees to finish exactly .500. That leads to a managerial change, as Jerry Leak decides to retire after the disappointing season.

The Pirates and their recently signed free agent closer Mariano Rivera win the World Series over the White Sox. In the draft, a second baseman named Robinson Cano is selected by the Giants, while the Yankees get third baseman Jose Bautista.

2001: 86-76, 3rd in AL East, 1.5 GB, Team WAR Leader: CF Carlos Beltran (6.6)

James Liness is hired as the new manager, while Clemens leaves in free agency. The Yankees decide to bolster their lineup even more and trade for Sammy Sosa, who has one-year left on his contract.

The Yankees are improved, but in a brutal bit of bad luck, they finish one game back of an Orioles/Blue Jays tie at the top of the AL East and the Wild Card-winning Athletics.

The Mike Mussina and Bobby Abreu led Angels take home the World Series. In the draft, the Yankees take pitcher Matt Cain.

2002: 94-69, 2nd in AL East, 1 GB, Team WAR Leader: CF Carlos Beltran (9.9)

The brutal disappointment of the year before leads to a quick managerial change as Mark Nocciolo is brought in.

The Yankees take another step forward thanks to an incredible season from Beltran and excellent ones from free agent acquisition Gary Sheffield and Thome. Even with that, the Yankees needed a game 163 win over the White Sox to win the Wild Card.

In the playoffs, the Yankees took the Tigers and the AL best record to game five in the ALDS but ultimately coming up short. The division rival Red Sox would go on to win their first World Series since 1935, breaking a “curse” of sorts.

2003: 93-69, 2nd in AL East, 5 GB, Team WAR Leader: CF Carlos Beltran (9.9)

Sheffield comes back on another one-year deal, and the Yankees make further additions to their offense with Luis Gonzalez and a shortstop named Derek Jeter on three and one-year deals, respectively. Clemens also comes out of retirement after having left the game following the 2001 season.

A late season slide not only leaves the Yankees five back of the Red Sox in the division, but it leaves them a game short in the Wild Card race and out of the playoffs. Boston would advance out of the AL, but fall to the Astros in seven games in the World Series. In the draft, the Yankees select a pitcher named J.A. Happ in the first round.

2004: 72-90, 4th in AL East, 30 GB, Team WAR Leader: SP Johan Santana (8.4)

The Yankees make yet another managerial change and promote bench coach Jeff Kolb to the big job. The let Jeter go elsewhere after just one year and sign David Eckstein on a multi-year deal to play shortstop.

Despite having a decent offense and decent starting pitching staff, the Yankees run into just a torrent of bad luck, going 22-34 in one-run games, by far the worst record in the league in those situations. That causes them to fall way back in the AL East.

The Red Sox and their offseason acquisition Barry Bonds win their second title in three years. Earlier that season, Bonds had surpassed Willie Mays as the all-time home run leader. The Yankees high pick after their disappointing season gets them Jay Bruce in the draft.

2005: 75-87, 4th in AL East, 20 GB, Team WAR Leader: SP Johan Santana (6.6)

Over in the National League, the Montreal Expos move to Washington DC, bringing baseball to the US capital for the first time in several decades.

After an excellent career in the Bronx, Carlos Beltran opts to leave and signs a free agent deal with the Phillies. The Yankees try to help their already decent pitching by bringing in six-time Cy Young winner Randy Johnson on a one-year deal. The additions and subtractions end up with not much of a change in the Yankees’ fortunes.

Atlanta would take home the World Series, beating the Tigers. The Yankees get Justin Upton with their first round draft pick.

2006: 92-70, 2nd in AL East, 8 GB, Team WAR Leader: SP Johan Santana (7.2)

Santana’s continued dominance leads the Yankees to a Wild Card win and playoff berth. Awaiting the Yankees in the ALDS was the 111-win Mariners. However, Santana allowed just one run in 15 innings across two games, leading the Yankees to a series upset over Seattle.

In the ALCS, the Yankees matched up against the Red Sox and quickly fell behind 3-1 in the series. John Danks and Cliff Lee put in massive performances in Games Five and Six to force a decisive seventh game. There, the magic ran out and Boston won 8-3, and would take another World Series crown in the next round. After the season Bonds retires, finishing his career with 792 career home runs.

The Yankees take Starlin Castro in the draft, but don’t end up signing him. However, they do ink second round pick, first baseman Sean Doolittle, who also has a history as a pitcher.

2007: 63-99, 4th in AL East, 45 GB, Team WAR Leader: SP Johan Santana (6.0)

The Yankees try to boost their offense by signing nine-time All-Star catcher Ivan Rodriguez for four years. That did not happen as the team went in the exact wrong direction.

The Albert Pujols and Felix Hernandez led Devil Rays took home their first World Series title, beating the Rockies. In the wake of failing to sign Castro, the Yankees got two first round picks, which they use on David Price and Alexi Ramirez.

2008: 80-82, 4th in AL East, 31 GB, Team WAR Leader: SP Johan Santana (7.4)

The Yankees bring in Mike Mussina to try and help the pitching staff bounce back from the previous season. He helps the Yankees improve, but not enough to get back into contention.

The 112-win Mariners make up for their 2006 upset loss by winning the World Series, losing just three playoff games along the way. The Yankees take first baseman Eric Hosmer in the ensuing draft.

2009: 83-79, 3rd in AL East, 22 GB, Team WAR Leader: SP Cliff Lee (10.0)

The Yankees sign Carl Crawford and Ben Sheets in free agency. They also make a managerial change, with Kolb departing after five seasons and Lloyd Breshers getting the gig. An incredible season by Lee helps the Yankees take another step forward, but still not a big enough one.

The Tigers would beat the Cubs in seven games in the World Series. In the draft, the Yankees add Whitt Merrifield and Ji-Man Choi in the first two rounds of that year’s draft.

Yankees 2000s Award Winners

• Takashi Saito: Reliever of the Year 2006
• Don Mattingly Hall of Fame Class of 2002 (Inducted as a Dodger)
• Tony Gwynn Hall of Fame Class of 2006 (Inducted as a Twin)
• Rickey Henderson Hall of Fame Class of 2009 (Inducted as a Brewer)