Frankly, it's because they haven't had to.
New York's last season finishing under .500 came in 1992. That's 24 years ago. In those 24 years, the Yankees have made the playoffs all but five times, winning five World Series.
The 2016 Yankees are historic. They're 53-52 and in jeopardy of breaking this ridiculous streak of great Yankees teams.
And now, at the trade deadline, the Yankees also did something historic. They sold. And, boy, did they sell big.
Looking at it as a whole, the Yankees made five trades involving Major League players.
They traded away Aroldis Chapman, Andrew Miller, Ivan Nova, Carlos Beltran and Vicente Campos.
They received Gleyber Torres, Adam Warren, Billy McKinney, Rashad Crawford, Clint Frazier, Justus Sheffield, Ben Heller, J.P. Feyereisen, Tyler Clippard, Dillon Tate, Erik Swanson, Nick Green and two players to be named later.
At the trade deadline, the Yankees pretty much added an entire 25-man roster. (Okay, in reality, they really added 14 new guys, but you get the gist.)
Prior to this season, the Yankees had a decent farm system. They ranked 16th in the Majors on Baseball Prospectus' farm system rankings, moving up five slots from 2015. But these trades really made their future team so much better.
The team added baseball's No. 22 prospect, No. 24 prospect and No. 93 prospect, almost doubling the number of Top 100 prospects in their system. Of their Top 30 prospects, five have come over via these July/August trades.
Yankees owner Hal Steinbrenner did something that goes 100 percent against his business model: giving in. Hal and the Yankees have proven that they want to be winners season-in and season-out. They're willing to go big or go home on free agents and take on huge payrolls. But the Yankees have never done something like they just did this past month.
And honestly, that just shows where baseball is at these days.
When the Yankees know the importance of prospects, a rebuild and the future, the parity of baseball shines through. The Indians are going for the American League championship this year, the Cubs are going for the National League championship and the Yankees are content with building for the future.
Brian Cashman did a great job at this trade deadline. He understands that, in order to build the next great Yankees dynasty, they needed to get rid of their current one. In a seller's market like this one, Cashman and company could not have chosen a better time to move their big trade chips and start planning for the future.
So my biggest winner at the 2016 trade deadline? The New York Yankees, who have given up for the first time since George H.W. Bush was in office.