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5 biggest questions Yankees must answer heading into offseason

The offseason is now upon the Yankees, a team that didn’t believe they would find themselves here at the end of the season. This was a World Series contender yet again that fell way short of expectations, barely making it into the postseason before a quick exit.

Because of that, change is coming to this roster. Maybe even a manager change as Aaron Boone’s contract is up.

From the top of the organizational chart with Hal Steinbrenner & Co. to the bottom, the Yanks are sick of being in this position, especially with the talent group they possess.

Something has to give, which means it’s back to the drawing board to figure out what to do with the current roster and how it can improve with additions via free agency and/or trade.

Let’s take a look at the five biggest questions the Bombers must answer this offseason with making it back to the World Series, once again, their burning desire:

1) Which pitchers should they target?

Drop all the current hurlers on the white board — rotation and bullpen — and figure out who stays and who goes. Because there needs to be a shift on both ends.

In the rotation, Corey Kluber is a free agent, and after being sidelined for a significant chunk of the season with a shoulder injury, you’d expect the 36-year-old to move on from New York.

That leaves Gerrit ColeLuis SeverinoJameson TaillonJordan Montgomery, and Domingo German as your rotation. Looks solid on paper until you factor in Severino returning from Tommy John surgery on Sept. 21 and not proving anything for next year, though he did appear to have some good stuff in his limited appearances.

Taillon had an up-and-down first season with New York, so he can’t really profile as Cole’s No. 2. Montgomery and German are good back-end pieces, but that’s all that should be expected of them.

In turn, someone for the rotation needs to be added to the mix. Kevin Gausman, Carlos Rodon, Robbie Ray and others will be available. Realistically, the Yanks should push for a No. 2-type of arm because Cashman already tried to take a risk with Taillon and Kluber and it didn’t turn out too well.

For the bullpen, Joely Rodriguez has a club option and Lucas Luetge is a free agent. Zack Britton’s baseball future is also up in the air, so the Yanks should be looking here, too.

Also worth noting: Luis Gil proved he can get the job done starting. Maybe his high-octane stuff could be used in the bullpen, too. He’s worth watching and putting into the equation as well for New York.

2) Do they go after a shortstop?

This could be a two-parter because it directly ties in with Gleyber Torres. This past season and the shortened 2020 campaign proved that Torres isn’t a viable option at short — he was worth minus-10 defensive runs saved in 2021, per FanGraphs. And all fans know how many All-Stars at the position will be available via free agency.

Carlos Correa, Corey Seager, Trevor Story, and Javier Baez will all be free agents, and they will all have numerous teams contacting their agents to figure out the price.

Seager’s left-handed bat is intriguing, though Correa’s skills defensively and offensively could arguably make him the most sought-after guy on the free agent block. And then there’s Story, someone the Yanks were attached to during the trade deadline earlier this year, and Baez, who has already been acclimated to New York with the Mets. Both players have pop and can be stuck in the middle of the lineup with good hands at short.

And many forget that Marcus Semien, who had a career year with the Toronto Blue Jays, will also be on the market. SNY’s Andy Martino explained why a short-term deal for Semien would make sense for New York.

It’ll be a tough decision, but this many stars being available at once won’t happen again any time soon. So the Yanks will need to think about what they want to do at this crucial position.

3) Can Aroldis Chapman be trusted?

He’s got one more year left on his contract before he’s a free agent in 2023, but forget about that. This season showed a very inconsistent version of The Cuban Missile, so much so that the Yanks must think hard about this question.

The closer on a World Series contender can’t make coaches and fans close one eye and bite their fingernails when he gets the ball. Cool, calm, collected is what this pitcher needs to be. While Chapman still throws hard, and sometimes his wild nature can be an advantage, he’s blown numerous saves to the point where he couldn’t be pitched in close games. Not good.

Internally, the Yankees could consider someone like Jonathan Loaisiga, who had a tremendous season pitching in high leverage situations. But he may not be ready to be called upon every ninth inning just yet. He’s the perfect setup man.

Raisel Iglesias will be available via free agency, as will Corey Knebel and Mark MelanconCraig Kimbrel also has a $16 million club option with the Chicago White Sox, who could exercise it after his successful year. But who knows?

Jun 30, 2021; Bronx, New York, USA; New York Yankees manager Aaron Boone (left) takes relief pitcher Aroldis Chapman (right) out of the game against the Los Angeles Angels during the ninth inning at Yankee Stadium.
Jun 30, 2021; Bronx, New York, USA; New York Yankees manager Aaron Boone (left) takes relief pitcher Aroldis Chapman (right) out of the game against the Los Angeles Angels during the ninth inning at Yankee Stadium.

4) What should be done with Gary Sanchez?

This isn’t a matter of getting rid of him — at least not yet. But between his inconsistencies in the batter’s box and behind the plate, it has become a recurring theme for some time now.

This time, though, he is entering his last year of arbitration before he becomes a free agent. One would think the Yanks figure out a contract for 2022, but this question is more long-term because it’s time to pay their homegrown guys.

But with money needing to be spread elsewhere (another player is more deserving which we’ll get to in a second), should Sanchez be extended and made the long-term catcher?

The free agent market for 2022 and 2023 is pretty barren, but Austin Wells – the Yankees’ first-round pick in 2020 and their current sixth overall prospect per MLB Pipeline — could reach the bigs in 2023. Whether or not that’s as a catcher is still to be determined, but you get where I’m coming from here.

Sanchez has made it hard on himself to generate a new deal, so that conversation has to start now.

New York Yankees right fielder Aaron Judge (99) in the dugout after he hits a home run during the eighth inning against the Chicago White Sox at Guaranteed Rate Field.
New York Yankees right fielder Aaron Judge (99) in the dugout after he hits a home run during the eighth inning against the Chicago White Sox at Guaranteed Rate Field.

5) Should Aaron Judge be extended now?

Judge was the Yankees’ MVP all season and will generate some votes for the AL MVP, too, though Shohei Ohtani deserves it. Still, he’s done exactly what the Yanks wanted: Play a full season at an All-Star caliber. So, with one year left of arbitration, is it time to extend the slugging right fielder?

The answer should be yes just to get it out of the way and lock in the face of your franchise. Judge has the potential to be the first Yankees captain since Derek Jeter, and that’s the type of aura he already carries every time he steps on the field. And he’s gotten the results to prove it, too.

Of course, there is the injury history that needs to be factored in. But, with question marks surrounding other players that need a pay day, why not just work hard on getting Judge’s deal done – either before or midway through the season – and don’t allow him to sniff free agency come the end of 2022.

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