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.
Reset
When the 2003 offseason started, The Yankees were coming off of a stunning World Series loss to the upstart Florida Marlins.