New York Yankees: Five burning questions entering offseason

19 FEB 2016: New York Yankees relief pitcher Dellin Betances (68) and New York Yankees relief pitcher Aroldis Chapman (54) during a New York Yankees Spring Training workout at George M. Steinbrenner Field in Tampa, FL. (Photo by Cliff Welch/Icon Sportswire) (Photo by Cliff Welch/Icon Sportswire/Corbis/Icon Sportswire via Getty Images)
19 FEB 2016: New York Yankees relief pitcher Dellin Betances (68) and New York Yankees relief pitcher Aroldis Chapman (54) during a New York Yankees Spring Training workout at George M. Steinbrenner Field in Tampa, FL. (Photo by Cliff Welch/Icon Sportswire) (Photo by Cliff Welch/Icon Sportswire/Corbis/Icon Sportswire via Getty Images) /
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(Photo by Tim Warner/Getty Images)
(Photo by Tim Warner/Getty Images) /

After a heartbreaking game six loss in the ALCS, the New York Yankees enter the offseason looking to answer these five burning questions.

Coming off of their second consecutive season with 100 or more wins and despite an unprecedented number of injuries, the New York Yankees looked unstoppable at points this season.

As with all things, however, all good things must come to an end. Unfortunately for the Yanks, it came in heartbreaking fashion in game six of the ALCS against the Houston Astros.

In being eliminated from the postseason, the 2010s will officially be the first decade since the 1910s in which the Yankees don’t make a World Series appearance. Now, as if things couldn’t be worse, the team faces a slew of questions that desperately need answering before the 2020 MLB season.

What’s more, the team is likely to look drastically different as veteran lefty CC Sabathia has vowed to retire, Brett Gardner could possibly not return, and several familiar faces are set to test free agency for the very first time.

So, how can the New York Yankees return to the promised land and deliver the team’s 28th World Series? Brian Cashman and the front office will have to answer these five burning questions in order to have a chance.