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Yankees' Next Big Moves Will Make or Break New Era's Future

It's not easy to do what the New York Yankees have done. It's even tougher to do what they have to do next. 

In this era in which total rebuilds are all the rage and tanking is rewarded, the Yankees rebuilt their farm system without also suffering through a 101-loss season (like the Chicago Cubs) or 324 losses over three campaigns (like the Houston Astros). Three years after said they had none of the top 60 prospects in the game, they have five of the top 51.

That doesn't even include Gary Sanchez, who turned 24 in December but graduated from prospect status when he hit 20 home runs in just 53 contests in 2016.

"The Yankees have the best (and deepest) farm system in the game,"'s respected prospect analyst Jim Callis tweeted in December.

Great, so now they'll start winning, just like the Cubs did?

Not so fast.

"This is still a building year for them," said a National League scout who follows the Yankees and their farm system closely.

This is a building year, for sure, but it's also a crucial year. For all the good work general manager Brian Cashman and his staff have done, and for all the patience managing general partner Hal Steinbrenner has shown, they haven't yet built a team that can win.

You don't win with a rotation headed by Masahiro Tanaka, Michael Pineda and CC Sabathia, with nothing but question marks behind them. You don't win with uncertainty at so many positions in the field.

The Yankees didn't build to win last year (when they were the only team not to sign a major league free agent), and they haven't built to win this season (when they spent big on closer Aroldis Chapman and basically swapped Brian McCann for Matt Holliday as their designated hitter).

They're trying to remain competitive while building for what could be a bright future, and so far, they've done a good job with that.

The Yankees haven't won a postseason game since the 2012 Division SeriesDerek Jeter, Robinson Cano, Curtis Granderson and Raul Ibanez played in that gamebut they also haven't had a losing season since 1992.

But how do they get from here (impressive rebuild) to there (true championship contender)?

"The biggest issue they have, by far, is starting pitching," the NL scout said. 

In his view, the Yankees need to find a way to trade for Jose Quintana, who may not be an ace but is a 27-year-old left-hander who is already a solid major league starter. The problem, the scout acknowledged, is that the Chicago White Sox have been looking for prospect-heavy deals like the ones they made for Chris Sale (with the Boston Red Sox) and Adam Eaton (with the Washington Nationals).

"They're asking for blood and more," the scout said.

The Yankees weren't going to gut the farm system they just rebuilt to get Sale, so they certainly won't do it for Quintana. If they can get him for what they deem a reasonable price, though, a Quintana trade would be a good place to start.

If not, then just wait.

With or without Quintana, the Yankees likely won't win in 2017. There aren't other obvious rotation upgrades available right now, but there will be. Unless he signs an extension, Jake Arrieta will be a free agent next winter. The Detroit Tigers would trade Justin Verlander for the right price. Clayton Kershaw can opt out of his contract after 2018. So can David Price.

If they don't do anything stupid between now and then, the Yankees will be in position to chase whichever ones they want.

Mark Teixeira and Alex Rodriguez are already gone. Sabathia's contract expires after this season. The Yankees might get under the luxury-tax threshold next winter, and in any case, they have just $74.2 million committed to five players for 2019.

There will always be speculation the Yankees will spend a big chunk of that money to sign Bryce Harper, who can be a free agent after 2018. In December, my friend Ken Davidoff of the New York Post named Harper "most likely to be a Yankee" out of the 2018 class.

I don't doubt it, but so much depends on what happens between now and then. Can Harper recover from a subpar 2016 season? Will a big-hitting outfielder even be the Yankees' most pressing need then? Would they be better off signing Manny Machado to play third base? Will they need to spend all their money on pitching?

Things change from year to year, as the Yankees know only too well. Twelve months ago, Luis Severino was one of the stars of the rebuilding process, a front-end starting pitcher ready to blossom. Now, the Yankees aren't even sure he's a starting pitcher at all.

They need to find out more this year about Severino and about fellow young starters Luis Cessa, Chad Green and Bryan Mitchell. They need to see if the progress James Kaprielian showed in the Arizona Fall League was real and whether fellow pitching prospects Justus Sheffield and Domingo Acevedo develop as true rotation options.

They need to find out if Greg Bird is the answer at first base and whether Aaron Judge can overcome his swing-and-miss issues to be a dependable power source in right field. They need to watch shortstop Gleyber Torres and outfielder Clint Fraziertheir reward for trading Chapman and Andrew Miller last summer.

"I think Frazier is playing right field for them before the year's over," the NL scout said. "And I wouldn't be surprised if Torres plays second, with [Starlin] Castro moving to third."

It's nice for the Yankees and their fans to think about, because it's fun to imagine talented players developing. But it's also a challenge, because the next decisions will cost more (in money and/or prospects) and have bigger consequences.

Two decades ago, the Yankees made all the right decisions at a similar point. They kept Jeter and Andy Pettitte and Mariano Rivera while trading highly rated (but not as good) prospects like Matt Drews and Russ Davis.

They built a team that won year after year. They dream of doing it again.

The decisions they make over the next 24 months could determine whether it happens.


Danny Knobler covers Major League Baseball as a national columnist for Bleacher Report. 

Follow Danny on Twitter and talk baseball.

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