Yankees: More Questions than Answers Heading into Offseason

The New York Yankees missed the playoffs for only the second time since 1995, winning only 85 games. The last time they missed out on the postseason — 2008 — the Yankees responded with their 27th World Series crown a year later.

It will feel much like a changing of the guard and an end of an era, with Mariano Rivera and Andy Pettitte retiring. Beyond that, the Yankees have the added uncertainty of what happens with Alex Rodriguez, who began his grievance hearing over his 211-game Biogenesis-related suspension on Monday. The team also must find a way to re-sign its best player, Robinson Cano, as the talented second baseman hits the free agent market reportedly wanting a record $305 million deal.

Hovering over the entire process is the team’s long-hinted desire to get under the $189 million luxury tax threshold. Once fans step back from all the warm and fuzzy memories stemming from the Rivera retirement tour, they’ll face this harsh reality. Five years later — in a baseball landscape that includes the Pirates back in the playoffs — the road back to relevance will not be nearly as simple for the Bombers as it was five years ago.

Issue No. 1: They’re old

At an average age of 30 years, the 2013 Yankees had the oldest roster in baseball. That number will decrease next year with 40-somethings Rivera and Pettitte retiring. Even so, the Yanks’ potential starting infield in 2014 could feature Robinson Cano (31) as the youngest member, pending the catcher position and Alex Rodriguez’s status. Jeter will turn 40 during the season and still hasn’t fully recovered from the broken ankle in the 2012 ALCS. Mark Teixeira, 34 in April, returns after a wrist injury cost him all but 15 games in 2013.

The Yankees will go into the winter with three outfielders — Vernon Wells (35), Alfonso Soriano (38) and Ichiro (40) — under contract for 2014. Fortunately the Angels and Cubs are picking up $32 million of the nearly $40 million owed Wells and Soriano next season. If they decide to re-sign Curtis Granderson he’ll be 33 come March.

Issue No. 2: Their farm system has been barren

The Yankees’ two-decade era of success was equal parts smart trades, free agent signings and young home-grown players, like Bernie Williams, Derek Jeter, Jorge Posada, Pettitte and Rivera all coming together. The 2013 Yankees were beset by injuries to their aging core, but didn’t have adequate players in the minors to fill the gaps, with guys like David Adams failing to make an impact at the major league level. The Yankees have done an okay enough job signing amateur free agents like Cano, but the draft record remains very poor. It left Brian Cashman patching over holes with scrapyard pickups like Lyle Overbay, Mark Reynolds, Brendan Ryan, etc. throughout the year.

New York does have some catching prospects (20-year-old Gary Sanchez) and some talented outfielders (Slade Heathcott, Mason Williams), but they remain a season or two away. Michael Pineda hasn’t pitched in the Majors since 2011 and if he’s finally healthy it helps, but the highly-touted twosome of Dellin Betances and Manny Banuelos seem to be a pair of over-hyped Yankee farmhands. Meanwhile, the last expected impact pitchers through the system, Phil Hughes and Joba Chamberlain, appear on their way out this winter via free agency.

Tom Verducci broke it down earlier this summer, noting Nick Johnson’s 33 home runs are the most round trippers the Yankees have gotten from a player they’ve drafted since 1993 — a year after they picked Jeter in the first round. It’s one thing to develop homegrown stars, but most big league clubs should have some adequate fill-ins down on the farm. Right now the Yankees have neither.

Issue No. 3: Minimal flexibility

When the Yankees missed the playoffs in 2008, the team responded with nearly half a billion dollars worth of contracts to Mark Teixeira, CC Sabathia and AJ Burnett. It paid off immediately with a 2009 World Series title. They’re paying the butcher’s bill for it now.

Besides Cano, the Yankees also have free agents to possibly re-sign in Granderson and Hiroki Kuroda. Brett Gardner, David Robertson (an adequate ninth-inning replacement for Rivera) and Ivan Nova — three of the team’s better young-ish players — will be due raises through arbitration.

Issue No. 4: Luxury taxed

This is the great unknown for the Yankees and perhaps all of baseball this winter. Will the Yankees actually hold their payroll below $189 million? Until this season the Yankees were over $200 million from 2008-2012.

As of today the Yankees are locked into $89 million for next year’s payroll — $72 million for A-Rod, Teixeira, Sabathia — plus what they’ll have to hand out in arbitration and if they re-sign Cano. All year rumors have swirled the Yankees want to get under the $189 million luxury tax threshold. In short, since they’ve been over that figure for numerous consecutive seasons, the Yankees are taxed 50 percent for every dollar over $189 million. If they dip under the threshold for a season, it resets to 17.5 percent and then 30 percent for the next two years.

Yahoo!’s Jeff Passan breaks it down in depth here. There are scenarios the Yankees could save upwards of $30 million if they take the one-year hit and get under the tax.

The questions: why would the mighty Yankees worry about a couple million when they’re a billion-dollar operation? Would this ever happen if George Steinbrenner were still alive? More importantly, with a roster full of holes and a poor farm system, how can the Yankees afford not to bring in some talent?

Yankees fans vote with their wallets. they won’t stand for a five-year Sandy Alderson-like rebuilding process as seen across town at Citi Field. If A-Rod is suspended and Cano opts to play elsewhere, the Yankees’ biggest selling point could be Jeter in his potential last hurrah.

Issue No. 5: The AL Cupcake Schedule is gone

In the late 90’s and early 2000’s the Yankees were a juggernaut, but they still fattened their record on 18/19 games each season with the Rays and Orioles. From 2001-2007, the year before the Rays made the World Series, the Yankees combined record vs. the two AL East foes was 171-89. In 2004 New York went 29-9 vs. the two clubs.

Now the Orioles are pointed in the right direction with Buck Showalter and the Rays will again play in the postseason.

These things are cyclical — the Yanks were 14-5 vs. the Blue Jays in 2013 — but the American League East doesn’t have the pushovers it once did when the Yankee Dynasty was at its full pomp.

Issue No. 6: the Free Agent crop is weak:

The Yanks have the No. 1 free agent on the market, their own guy: Cano.

They also have one of the best best free agent pitchers in Kuroda.

Some of the other names on the market include Jacobly Ellsbury, Shin-Shoo Choo, Justin Morneau and ~~Hunter Pence~~. If the Yankees want to spend to shore up the catching position, they could throw a lot of money at Brian McCann, or else its one-year fliers on guys like Jarrod Saltalamacchia or Carlos Ruiz. If A-Rod is suspended the options at third base include Michael Young, Kevin Youkilis, Placido Polanco or even Brandon Inge. Slim pickings.

Today the 2014 Yankees’ rotation is Sabathia and Nova plus a bunch of question marks. Free agent pitchers this winter include: Matt Garza, Tim Lincecum, Bronson Arroyo, Dan Haren, Bartolo Colon (Cashman is likely drooling to sign Bart), Josh Johnson, Ricky Nolasco and Ervin Santana. Solid starters, but will the Yankees be willing to pay $10+ million per season for them? Can they if they want to stay under the $189 million mark?

Chances are the Yankees will be contenders again, sooner rather than later. It all depends on how serious they are about keeping payroll down. Beyond that, trying to patch it back together via free agency might not be a panacea since baseball’s new landscape also includes teams like the Pirates and Reds locking up their own homegrown stars like Andrew McCutchen and Joey Votto before they ever hit the market for the Yankees to gobble up as they did in the past.

These are the most questions baseball’s flagship franchise have faced since the days of Roberto Kelly and Danny Tartabull.