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.

(Photo by Alex Trautwig/MLB Photos via Getty Images)
(Photo by Alex Trautwig/MLB Photos via Getty Images) /

New York Yankees: 5 Burning Questions

Will Aroldis Chapman opt out of his contract?

As Aroldis Chapman walked off the field in game six of the ALCS having given up a walk-off home run to Jose Altuve, he wore a smile on his face. Don’t be mistaken, the smile was most certainly a mask hiding all the frustrations building up inside.

Now, he will face one of the toughest decisions of his career: whether or not to opt-out of his current contract.

If Chapman decides to walk away from the remaining $34.5M of his contract, he could be risking falling under the same circumstances as another elite closer: Craig Kimbrel.

Kimbrel struggled to find a team last offseason and ended up starting the 2019 MLB season in free agency. It wasn’t until the Chicago Cubs became desperate mid-season that he was able to secure a deal. By then he was only able to get a 3-year, $43M deal ($14.33M AAV) with vesting options.

Currently, Chapman’s deal pays him north of $17M per season through 2021. The only way I can see Chappy opting out is if he and the Yankees can come to terms on an extension, perhaps adding two more years to his current contract.

One thing is for sure, with bullpen arms being hard to find around the league, I can’t see the Yankees without Chapman next season.

My prediction is: he stays and gets two more years tacked on to his current deal.

(Photo by Adam Hunger/Getty Images)
(Photo by Adam Hunger/Getty Images) /

New York Yankees: 5 Burning Questions

Have we seen the last of Dellin Betances?

Dellin Betances missed just about all of the 2019 MLB season because of injuries. Without him, the New York Yankees managed to field one of the best bullpens in the game, reaching a game six of the ALCS.

In the past, Betances and the Yankees have butted heads over comments team president Randy Levine made about him in 2017. At the time, Levine ripped Betances’ salary request for 2017. In response, Betances threatened to limit his role and rethink his view of the organization.

Despite Betances being an elite reliever, all of this could spell the end for the New York-born reliever who is set to test free agency for the first time in his career. the Yankees will not want to pay him much more than the $7.25M he made in 2019.

What’s more, the Yankees already have a slew of relievers who have proven to be formidable assets for the team this season. Between Chad Green, Zack Britton, Tommy Kahnle, and Adam Ottavino, the team has more than enough arms to bridge the gap between the starter and the closer.

My prediction is: Betances, who will be 32-years-old at the start of the 2020 season, will begin the season elsewhere.

(Photo by Rob Tringali/MLB Photos via Getty Images)
(Photo by Rob Tringali/MLB Photos via Getty Images) /

New York Yankees: 5 Burning Questions

Will the Yankees acquire a top-flight starting pitcher?

The only weakness one can point to on the New York Yankees is starting pitching. Per fWAR, the team’s starting rotation was 17th best in all of MLB. Here’s how they fared in some other areas:

  • ERA – 4.51 (15th best)
  • FIP – 4.74 (18th best)
  • WHIP – 1.29 (10th best)

With the current rotation, the team doesn’t have a single starter who can exceed more than 200 IP in a single season. This puts a strain on the strength of this team: the bullpen.

The solution: target a bonafide starter. Someone who can carry the load for seven or eight innings.

The good news: there will likely be two starters willing to be the ace of the Yankees pitching staff.

The problem: this type of pitcher will cost the team a lot of money as they will be sought after by a number of teams.

By this point, you might have guessed that I’m talking about Gerrit Cole and Stephen Strasburg, two sure-fire aces.

Currently, the largest contract for a starting pitcher belongs to Red Sox lefty David Price. In 2016, he received a 7-year, $217M deal ($31M AAV). Cole and Strasburg will be looking to exceed that number, so any team vying for their arms should be looking to spend close to $35M AAV for either pitcher.

My prediction is: the Yankees sign Gerrit Cole to a 7-year deal worth somewhere between $230M – $250M.

(Photo by Cooper Neill/MLB Photos via Getty Images)
(Photo by Cooper Neill/MLB Photos via Getty Images) /

New York Yankees: 5 Burning Questions

Will Didi Gregorius return next season?

Didi Gregorius won the hearts of New York Yankees fans during the 2017 MLB postseason. It was then that he established himself as a clutch hitter in key situations for the team.

First, there was the three-run blast off of Minnesota Twins starter Ervin Santana tying the game in the first inning. Then there was the miraculous comeback against the Cleveland Indians in the 2017 ALCS capped off with a 2-home run game against one of baseball’s elite pitchers in Corey Kluber.

Cut to 2019 and Didi has fallen from grace a bit. This year, Gregorius had his worst statistical season with the Yankees. This has left many wondering if the fan-favorite shortstop will return next season.

A few things will play into this decision for the Yankees. First, are the Indians serious about trading Francisco Lindor?

If they are, the Yanks will most certainly try to make a run for the 25-year-old shortstop. The question is, what will they have to give up in return?

If Lindor is out of the question for the Yankees, then Gregorius will likely return to the team. He just means to much to the clubhouse and, frankly, the team still managed to win 100+ games with a sub-par performance out of shortstop.

My prediction is: Didi Gregorius stays in New York. The Yankees offer him a 5-year deal worth somewhere around $70M.

(Photo by Mark Goldman/Icon Sportswire via Getty Images)
(Photo by Mark Goldman/Icon Sportswire via Getty Images) /

New York Yankees: 5 Burning Questions

Who mans third base? Miguel Andujar, Gio Urshela, Neither, or both?

More from Call to the Pen

Let’s explore all of the options for the New York Yankees at third base. First, there’s Miguel Andujar, the Yankees’ first option at third entering the 2019 MLB season.

Andujar proved during the 2018 MLB season that he can hit with the best of them. However, defensively, he left a lot to be desired. He will be only 25 at the start of the 2020 MLB season and should improve some.

Then there’s Gio Urshela, who the Yankees absolutely love. He’s got the bat, the glove, and, frankly, the heart. There were times this season where Gio carried the Yankees. What’s more, he will cost the team approximately $600K this season.

Finally, there are some free agent options like Anthony Rendon. While these options are certainly the best, they are also the most expensive and let’s be real, the Yankees aren’t in need of elite hitters at this time. They have plenty of those

dark. Next. Two Red Sox players likely be dealt in huge trades

My prediction is: The Yankees include Miguel Andujar in a trade to fill a need elsewhere and keep Gio Urshela at third base.

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