Ever since the dawn of the 21st Century, the New York Yankees have prided themselves on the idea of winning now. Each year, they put themselves in a position to win the World Series. This has meant spending enormous amounts of money on players and hemorrhaging their farm system for players they couldn't get in free agency.
To their credit, it has worked fairly well. Since 2000, they have won nine AL East Division titles and two wild card berths, meaning they have made the playoffs every year except 2008. In the playoffs, they have won the AL Pennant four times, 2000-03 and 2009. They have also won the World Series twice, in 2000 and 2009.
But all good teams have periods of winning usually followed by a subpar year here and there. The Yankees have not. Their insistence on always winning the World Series has forced them into bad decisions and even worse contracts. Usually they are able to alleviate these problems with trades and even more free agency signings. But eventually it catches up to anybody, even the Yankees. And when you watch the Yankees play now, you are watching the beginning of a downfall. You are seeing the dark underside of the "win now" philosophy.
The Yankees are in third place this season but just a game behind back. They very easily could make the playoffs this year. But their play shows concerns for the future, specifically with their aging stars. Alex Rodriguez is a rime example. In an act of desperation, the Yankees gave A-Rod a 10-year contract after he opted out in 2007 even after claiming they would not. He has rewarded them with seasons of declining performance and injuries. But because they felt they needed him in 2007, the Yanks gave him a deal that will see them pay him until he is 42.
And the Yankee roster is riddled with players signed to long-term, big-money deals that will, or already have, hurt them down the road. Players like Mark Teixeira, Derek Jeter and C.C. Sabathia come to mind. But the Yanks can't not be competitive, so they continue to make these deals. And if they start to cutback on payroll as their owners have suggested, they may not be able to make up for their mistakes. Instead, they will find that their entire roster is filled with aging, underperforming players that the Yanks signed when they couldn't imagine not winning today.