Guest Post: The Yankees’ non-existent strategy of keeping top prospects

Hey, I’m Ryan Kantor. I write a blog with my friend Tommy. Our blog is about sports, music, and politics, but we’re both Yankee fans and Lenny was nice enough to let me make a guest post on his wildly well-read Yankees Blog. So first of all, I want to thank Lenny for letting me do this and then I want to correct an incorrect perception.

You probably know about a lot of the young talent we’ve moved over the years (Mike Lowell, Ted Lilly, Jake Westbrook) but since we decided not to trade Phil Hughes and Joba Chamberlain for Johan Santana (great decision) there has been a perception that Brian Cashman is keeping all of our top prospects and aggressively building the farm season, and that just isn’t so.

In 2008 the Yankees moved a big package of talented prospects for just a little bit of major league talent. New York shipped talented outfielder Jose Tabata, and right-handed pitchers Daniel McCutchen, Jeff Karstens and Ross Ohlendorf to Pittsburgh. Tabata is now Pittsburgh’s young productive No. 2 hitter, and Ohlendorf has been a consistent arm in their rotation (I’d take him over A.J. Burnett and save the $16 million). The Yankees received Damaso Marte and Xavier Nady. Marte is currently on the DL while Nady is now on the Cubs.

This offseason, we moved another group of talented prospects in Phil Coke, Ian Kennedy, and most notably Austin Jackson for Curtis Granderson. Granderson’s struggles in New York and Jackson’s torrid start to the season have made some wonder if this was a wise move for the Yankees.

The point is not that Cashman is making bad trades and giving away prospects for nothing. Rather, it’s quite the opposite.

They gave up quite a lot for Marte and Nady. Nady only played in 66 games for New York, while Marte contributed a 5.40 ERA in 2008 and a 9.45 ERA in 2009. That being said, do you remember when Coke stopped getting people out in the 2009 postseason? Joe Girardi turned to Marte and he came through for them time and time again. Would we have won the World Series without him? Maybe, but who knows. Does the shiny set of rings justify the trade? Absolutely!

The Granderson trade looked pretty bad when Granderson was struggling and Jackson was raking, then Granderson went on the DL and it looked even worse. That said, would you rather have a rookie center fielder with two home runs and the AL lead in strikeouts or a 29 year old with some pop up at the plate in a meaningful October game?

The Yankees are at a point with their roster where it’s time to go all in. Exactly as the Los Angeles Lakers seem to recognize, Cashman and the Yankees know their core can only win 100+ games and add to the Yankees collection of World Series flags for another year or two. With Derek Jeter, Alex Rodriquez, Jorge Posada, Mariano Rivera and Andy Pettitte at the end of their primes and CC Sabathia, Burnett, Mark Teixeira, and Nick Swisher already deep into their primes, what will this team look like in three years?

A lot goes into being a great GM, knowing what your team needs is critical, but knowing when they need it most may be just as important. This could be their last shot to win it all before entering rebuilding mode, so Cashman is going all in and I applaud him. The Yankees are placing their bet on themselves, and giving it one or two more shots with Jeter, Posada, Rivera, and the classic Yankees we have come to know and love.

Here’s to #28!

Thanks, Ryan! Great stuff. Make sure to check out Ryan’s blog for more of his commentary.