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Brian Cashman’s biggest blunder

Brian Cashman  is currently presiding over a long and prosperous run as the General Manager of the New York Yankees. Over the past 21 years, Cashman has won five titles and seven pennants. He has also won the respect of fans, reporters, and fellow executives.

Despite his accomplishments, one decision that often gets swept under the rug is the decision to let Andy Pettitte walk in free agency following the 2003 season. This was Cashman’s biggest failure as GM, and it cost the Yankees at least one championship.


When the 2003 offseason started, The Yankees were coming off of a stunning World Series loss to the upstart Florida Marlins. The Yankees had been heavy favorites going into the series, and there was a sense of exhaustion and frustration after the series ended. The ALCS took an emotional toll on the team. Additionally, Roger Clemens was set to retire, placing some uncertainty over the rotation and the team as a whole.

The start of the off-season

Once free agency began, George Steinbrenner and Brian Cashman zeroed in on one target: Gary Sheffield. Steinbrenner was absolutely enamored with Sheffield. He loved his swing, loved the fact that he was from Tampa, and loved that he was Dwight Gooden’s nephew. Steinbrenner famously wined and dined Sheffield in Tampa and signed him to a three-year deal on Dec. 1. (This was back when teams actually signed free agents before New Years.)

Moving along

Meanwhile, Pettitte hadn’t received a phone call from the Yankees. There were rumblings that Steinbrenner didn’t think Andy had the “bulldog” mentality that Clemens had. He had always thought Pettitte was a bit soft, and he famously tried to trade him at the 1999 trade deadline. None of this made any sense. Pettitte had gone 21-8 with a 4.02 ERA in 2003, was in the middle of his prime, and was on his way to becoming one of the greatest Yankee pitchers of all time.

Other Suitors

Pettitte was being heavily courted by the Red Sox and Astros while hearing nothing but crickets from the Yankees. On Dec. 8, Pettitte reached a verbal agreement with Houston on a three-year, $31.5 million deal. Only then did Cashman finally swoop in, offering slightly more money over the same three-year time period. This strategy had worked in the past, as both Bernie Williams and David Cone were signed at the last second after they were close to signing with other teams.

However, Andy is a man of principle and refused to go back on his word with Houston. He stood firm on his verbal agreement, and the left hander officially became an Astro on December 11th.

The Aftermath

The ramifications from this blunder were almost worse than the blunder itself.

Clemens decided to un-retire and join his buddy and fellow Texan in the lone star state. Cashman then traded for Kevin Brown, a fragile pitcher with a fragile ego who wound up on the disabled list twice in 2004. Cashman also brought in Javier Vasquez, a small market pitcher who was clearly overwhelmed by the bright lights and struggled mightily.

The Yankee rotation was mediocre in 2004, lacking an ace and any kind of identity.

It was fitting that Brown and Vasquez combined to cough up game seven of the 2004 ALCS against Boston, combining to allow six runs in under three innings. Cashman’s mistake had blown up at the absolute worst time. The Yankees’ season was over.

Digging Deeper

There were a lot of factors that went into this mistake. It’s only fair to note that big Stein was heavily involved, and we don’t know how much say Cashman actually had on the matter. We know that George was enamored with Sheffield and had soured on Pettitte. Despite this, Cashman was still the GM, and thus he must shoulder the responsibility.

With Pettitte on the 2004 roster, I believe the Yankees would’ve won the 2004 ALCS in six games and cruised past the Cardinals in the World Series. There is simply no way the Yankees lose four games in a row with Petttite on the roster instead of Vasquez or Brown. 2005 and 2006 are harder to project, but it’s obvious that having Pettitte in the rotation would have given the Yanks a better chance of reaching the World Series in both of those seasons.

It’s no coincidence that the Yankees didn’t win another World Series until Pettitte was back in the fold in 2009. Cashman quickly realized his mistake, and brought Andy back after the 2006 season, as soon as his contract with the Astros expired.

Andy had a great second stint with the Yankees, but it’s pretty obvious that they would’ve won at least one more World Series had Pettitte not left. Brian Cashman has been an outstanding GM for the Yankees, but this was an inexcusable error.