The New York Yankees and Brian Cashman are at a crossroads entering an offseason that will determine the future for both the franchise and its general manager of the last 15 years. 

Cashman has been a lightning rod for criticism for a long time. He’s almost become too easy a target because the Yankees have spent more money to put a team on the field than any other organization in North American professional sports, so how hard can it be to sit in that front office? 

All that money has helped lead New York to four World Series titles, 12 division titles and 14 playoff appearances during Cashman’s tenure, a resume no other franchise in Major League Baseball comes close to matching. 

However, the Yankees are broken right now with no immediate solutions on the horizon. They are locked into a number of bad contracts that will keep getting worse as these players age and their skills continue to regress. 

There is also the impending elephant in the room regarding All-Star second baseman Robinson Cano, who will hit free agency in November and command a huge bump in salary. The numbers suggest he would be a prudent investment for Cashman and the Yankees, but his age (31) is problematic since handing out big deals to old players is what has gotten this team in trouble. 

While it’s impossible to predict what will happen in free agency when you have teams bidding against each other, not to mention those pesky mystery teams that tend to drive prices up, it is safe to say Cano is going to get a sizable contract from someone. 

Sweeny Murti of CBS New York conducted a survey of 34 MLB executives posing the question, “What will Robinson Cano sign for?” He made a point to note that he didn’t ask what Cano was worth, since that is an entirely different question. 

The consensus had Cano getting a deal in the range of seven years and $181 million (average annual value: $25.9 million). 

If you were worried about Cashman and the Yankees not having the money to spend on Cano this offseason, remember 10 other players accounting for nearly $80 million of the 2013 payroll will also be free agents or retired. 

Of course, Cano is just the tip of the iceberg for Cashman this winter.

The general manager needs to rebuild his starting rotation, find a few hitters who aren’t walking shells of their former selves, and inject high-upside youth into the system. 

Speaking of, one big problem for the Yankees in recent years has been the lack of production from the farm system. For instance, they came into 2013 with a half-decent minor league group led by catcher Gary Sanchez and outfielders Mason Williams, Tyler Austin and Slade Heathcott.  

Here are the 2013 stats for the Yankees’ trio of top prospects. 

You can’t always judge a prospect by stats, but just know that I saw Austin and Williams in the Arizona Fall League and can testify that those numbers aren’t an accident. Williams has a few tools, but he doesn’t project to do much with the bat to become the leadoff hitter everyone anticipated.

Austin has yet to prove himself at the Double-A level and missed time in 2013 due to a wrist injury, so there are concerns about how high his ceiling is. 

Sanchez has as much raw potential as any player in the minors, but the Yankees have disciplined him in the past for an attitude problem. His performance this season was not at the level you want to see from someone with his kind of tools. 

The Yankees’ drafts have gone horribly awry in recent years. Dante Bichette Jr., their first pick in the 2011 draft, had name recognition and not much else. Cito Culver, a first-round pick in 2010, was a huge overdraft and flamed out in the lower levels of the minors. Ty Hensley, the 30th pick in 2012, is 20 and pitched 12 innings in the Gulf Coast League this year. 

I did like New York’s first three picks in 2013 (Eric Jagielo, Aaron Judge, Ian Clarkin), but all of them have notable flaws that could prevent them from advancing past Double-A. And none of them have ceilings better than average regulars. 

The blame for New York’s lackluster drafting doesn’t fall entirely on Cashman’s shoulders. They are always picking at the back of the first round, where you aren’t going to find elite talent. 

No one is going to pay attention where you pick, though. All that matters is the players selected haven’t been working out. 

Cashman also has to deal with the failure of letting certain players walk away and trades that have not paid off. Yankees fans are still holding out hope that Michael Pineda will turn into a No. 1 starter even though he hasn’t pitched in the majors since 2011 and had just 40.2 minor league innings in 2013. 

Russell Martin, who hit 39 home runs in two seasons with the Yankees, signed a two-year, $17 million deal with the Pittsburgh Pirates last winter. He hit 15 homers with a .703 OPS in 127 games this year, compared to eight home runs and a .587 OPS for all New York catchers in 162 games. 

Cashman and the Yankees were so desperate for bodies this year they signed Kevin Youkilis, Travis Hafner, Lyle Overbay, Mark Reynolds and Ben Francisco just to fill out a lineup card. They also traded for Vernon Wells and apparently felt obligated to reward Ichiro Suzuki with a two-year contract after a mediocre three-month run last year. 

It isn’t clear what Cashman’s plan for 2013 was, or if he even had one. Perhaps the goal was to open up enough money for this offseason to spend on top free agents, in addition to re-signing Cano. 

If that’s true, it’s a poor strategy because this free-agent class is nothing to get excited about.

Shin-Soo Choo is the top position player after Cano, but Scott Boras represents him and is reportedly talking about a $100 million contract for the 31-year-old. 

Jacoby Ellsbury can be a dynamic talent when healthy, but he’s also missed at least 28 games in three of the last four years, including 88 in 2012 and 144 in 2010, and he just turned 30 on September 11. 

Brian McCann is not likely to stay behind the plate the older he gets. The 29-year-old has always been a marginal defender, putting more pressure on his bat to play at a high level as a potential DH/1B. He’s also missed significant time each of the last two years battling injuries. 

On the pitching side, do you trust Ervin Santana or Matt Garza pitching in the American League East with that short porch down the right field line in Yankee Stadium?

There are a lot of names available, but all of them have huge question marks regarding health, age and performance. The Yankees should think long and hard before trying to throw money at all their problems. 

This is another scenario that doesn’t bode well for Cashman because the Yankees aren’t going to have patience to endure another mediocre season like 2013. Fans and the media, especially in New York, will want heads to roll. 

As much as I like to think public pressure doesn’t force front offices and ownership of professional sports teams to act, there are examples of it happening every year in every sport that prove me wrong. 

In fairness to Yankees ownership, which has taken its share of hits in the last year because George Steinbrenner’s kids aren’t quite as frivolous with money as their father, they are still giving Cashman a great palette to work with. 

Even if ownership wants the payroll to get closer to the $189 million luxury tax threshold in time for the start of 2014, as reported by David Waldstein of the New York Times, that would still be more money spent to field a roster than 28 other teams (only the Dodgers’ payroll would be higher). 

Cashman and the Yankees have made a series of bad investments over the years that have come back to bite them now. It’s not a surprise; when you build around free agents, especially the top-tier, high-salary kind New York goes after, eventually things will collapse. 

It is Cashman’s job to mitigate the situation by offsetting bad contracts with young, cheap, high-upside alternatives ready to step in at a moment’s notice. Some moves he’s made had that in mind, like the Pineda deal, only to backfire. 

The Yankees are stuck in a rut. Now Cashman has to make the moves necessary to ensure it isn’t a sustained down period. If not, the future figures to get a little darker for one of the longest-tenured GMs in baseball. 


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