An era is rapidly coming to an end in New York, as Yankees pitcher Andy Pettitte is announcing his retirement effective at the end of the 2013 season, per the team’s official Twitter feed: 

With Pettitte announcing his retirement Friday, Mariano Rivera having a season-long retirement tour that will culminate in something special next week (barring a playoff appearance) and Jorge Posada stepping away after the 2011 season, Derek Jeter will be the last link to the Yankees and the dynasty that started in 1996, bringing five championships to the Bronx. 

But Jeter, 39, is also on his last legs, playing in just 17 games this year because of ankle problems stemming from the injury he suffered in last year’s American League Championship Series against the Detroit Tigers.  

The star shortstop has vowed to return for the 2014 season, but who knows in what condition he will be or how productive he can be, given his age and basically missing an entire season. 

All of this paints a dark cloud for a Yankees team that is also locked into a number of bad and/or expensive contracts for the next handful of years, including those of Alex Rodriguez, Mark Teixeira and CC Sabathia.

On top of that, there is the rather large question about Robinson Cano’s impending free agency. He remains New York’s best player by a wide margin, but how comfortable will ownership and Brian Cashman be handing a seven- or eight-year deal worth, say, $20 million to $25 million (or more) per season to a player who will be 31 at the start of 2014?


The End of the Line

There was a time when we just expected the Yankees to be great because they had seemingly unlimited resources and were always churning out prospects who would produce in the big leagues or make great bargaining chips to use in trades. They would find key components to a championship team in the least likely of places. 

Jim Leyritz came from the depths of obscurity to hit two of the biggest home runs of this Yankees run that started nearly 20 years ago, in Game 3 of the 1996 World Series and Game 4 of the 1999 Series, both against Atlanta

But that hasn’t been the case since the 2009 championship season. In fact, for many reasons, that felt like the last moment for this core group. They have played in postseason games since that time, yet they have not been able to claim that elusive 28th ring. 

And what’s so different about this particular iteration of the Yankees compared to past teams that have had their issues is you can’t see a clear, easy solution. 

The front office has built a roster that is old. According to ESPN, it is the oldest roster in baseball this season at 30.0 years. That wouldn’t necessarily be a bad thing if they had help on the horizon. 

Yet if you look at their farm system, the Yankees just aren’t developing players the way you need to in order to sustain success. That’s why we see them going out and trading for the likes of Ichiro Suzuki, Vernon Wells and Alfonso Soriano or hoping against hope that they can convince Hiroki Kuroda to keep taking one-year deals until he proves he can’t be an effective pitcher anymore. 

Left-handed pitcher Manny Banuelos was supposed to be a rotation stalwart after a breakout 2010 season, but he battled control problems in 2011 before having Tommy John surgery last year that forced him to miss all of 2013. 

Dellin Betances never threw enough strikes to be a starter, despite having a very good arm. We keep hearing that Michael Pineda is on the road to recovery, but he has thrown 40.2 innings the last two years. 

Top position players such as catcher Gary Sanchez and outfielders Mason Williams, Tyler Austin and Slade Heathcott all regressed this season, and their future ceilings are now much less clear than they were before the 2013 season started. 

In the past, if the Yankees wouldn’t have had a spot for those players, they would have at least been able to shop them around to acquire someone like Pineda, who was one of the best young stars in baseball after his impressive rookie season in 2011.

The Yankees did give up Jesus Montero, widely regarded as the best pure hitting prospect at the time, in the Pineda trade, but they did it without putting a huge dent in their system because they had accrued so much depth. 

Now, with the big league team getting older and those accrued assets not developing as expected, the Yankees have a lot of questions. 


Immediate Future

We can talk all we want about the Yankees possibly making a trade to upgrade their roster. That’s what New York/baseball fans do.

They get it into their heads that all you have to do is a make a trade with some team for one of their best players and it will all be OK, because why wouldn’t one of the 29 other MLB clubs be willing to deal with the almighty Yankees?

I hate to break it to those fans, but that’s not how things work. Remember when the hot rumor was the Yankees would be getting Felix Hernandez from Seattle? It was almost like it was inevitable, because these are the Yankees we are talking about. 

Well, if you want to trade for arguably the best pitcher in baseball, you need a package attractive enough to get the Mariners to say yes. They didn’t have it then and certainly don’t have it now (not that Hernandez is up for grabs today, after signing a long-term extension). 

Whom are the Yankees going to get in the offseason? If we factor in the money it would cost to re-sign Cano—who will stay, I think, though I feel less sure about it than I would have one year ago—will they be able to take on another big contract?

They will free at least $90 million in salary once the season ends, possibly as much as $99 million if Derek Jeter exercises his 2014 option at $9.5 million (he made $17 million this year). 

For instance, the No. 2 free agent on the market this winter is Shin-Soo Choo. The Yankees have a need for an outfielder, with Curtis Granderson hitting free agency. Choo is still a tremendous hitter with a .426 on-base percentage and .466 slugging percentage with Cincinnati

But a player with those numbers in a walk year, as well as the consistent level of performance he has shown since 2008, could realistically command a four- or five-year deal at $15 million to $20 million per season. 

Is it worth it for the Yankees to invest that kind of money in another 31-year-old outfielder whose defensive skills have been declining?

On the pitching side, do you want to invest a big contract in the oft-injured and at times underperforming Matt Garza? Is Tim Lincecum going to make a difference in a hitter’s park? 

We don’t know what the trade market is going to look like, but I would bet there isn’t a lot of love for the Yankees’ system right now that helps them net an impact player. 


A Sad Dose of Reality

What the retirement of Pettitte and Rivera, as well as the questions about Jeter’s future, represent is the first time the Yankees have to seriously think about rebuilding since this era started. 

I know this is New York, and the team is always going to have a payroll over $150 million and be expected to compete for a championship every year. But look around and see what is staring you in the face. 

Things are going to get worse before they get better, to steal a line from Michael Caine in The Dark Knight. That the Yankees have been able to hang in the playoff race this year given all the injuries and poor performances from key players is a minor miracle.

But you have to be kidding yourself if you think Soriano is going to slug .523 in a full season; or Alex Rodriguez will play in 110-120 games (assuming he gets some kind of suspension) and post an .808 OPS; or Ivan Nova will post a 3.36 ERA giving up 1.3 baserunners per inning and a pedestrian 2.48 strikeout-to-walk ratio. 

They might be able to do what they have done this season, which is hang around .500 and be in contention for the second wild-card spot in the American League. But they can’t compete with Boston, Tampa Bay, Oakland, Detroit or Texas as things stand right now. 

This era of Yankees baseball, for all intents and purposes, is over. It’s time for the front office to plan for the next one while also realizing that it’s going to take time to get there. 


If you want to talk baseball, feel free to hit me up on Twitter with questions or comments. 


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