Anthony McCarron, SNY.tv | Twitter |

With a strong, young nucleus of stars such as Aaron Judge, Gleyber Torres and Luis Severino and others, the Yankees at least have the base of a contender for years to come.

But that doesn't mean there aren't significant questions facing GM Brian Cashman and the Yankee braintrust this offseason after another disappointing exit from the playoffs. And winning windows sometimes close before we think they will, if clubs don't make the right moves.

Will it be a long, Cole'd -- get it? -- winter? Will Aroldis Chapman opt-out? Who's on first? (No, seriously).

Sure, the sting of losing to the powerful Astros will linger. But the Yanks must throw themselves into free agency, roster construction and, perhaps, the trade market, to see if they can change the narrative next year.

Here's a look at some of the issues the Yankees face in preparing for 2020:

Will they sign Gerrit Cole?

Cole, the Astros' dynamo, will be the top free agent starter available. The Yankees, as well as any team with a pitching brain, love him, and based on their 4.51 starters ERA this year (15^thin baseball, just 0.03 below the MLB average), he figures to be a target.

The Yanks drafted him in the first round in 2008 and hoped to sign the childhood Yankee fan, but he went to UCLA instead. Cole was born in Newport Beach and some theorize he's headed back to the West Coast to pitch. Can the Yankees sway him this time? If they don't get Cole, they need to add another big-time starter.

What happens if Chapman opts out?

Chapman threw the last pitch of the Yankees' season and José Altuve crushed it for the homer that ended the AL Championship Series. Chapman's disbelieving grin on the mound afterward is sure to be a lasting image of the Yankees' flameout (relax, he was just processing giving up the walk-off that send Houston to the World Series). But it won't be the last time we hear about him before spring training.

He can forgo the final two years and $34.4 million remaining on the five-year, $86-million deal he signed with the Yankees before the 2017 season. Chapman, who turns 32 in February, had a 2.21 ERA, 13.4 K/9 and a 1.11 WHIP for a bullpen that was a Yankee strength all season.

Will Chapman try for a longer deal on the open market? Or at least try to get the Yankees to pile on more years to keep him from even testing the market?

Who's the 2020 shortstop?

Didi Gregorius has been an exemplary replacement for Derek Jeter. Few could have done it as well. But he is a free agent and was not the same player in the 82 games he played after returning from Tommy John surgery. Sure, his emoji game remained strong and he seems an important clubhouse presence, but the Yanks have a potential replacement in-house in Gleyber Torres.

If the Yanks let Gregorius walk, they could slide Torres over from second and make D.J. LeMahieu the second baseman. Torres played 77 games at short this season while Gregorius healed.

Ifs at first

Yanks sure seem to have a lot of players who are first base/DH types, don't they? Even Miguel Andújar, who might play third, could be better off at first. Edwin Encarnación could come back on a $20 million option, or they could pay him a $5 million buyout. Luke Voit fizzled after he was hurt, but he may have been more compromised by his sports hernia than we knew. Where, if at all, does Greg Bird fit in? LeMahieu proved he can play the position, but is probably better served starting elsewhere on the diamond.

Third-base bind

Gio Urshela was a revelation this season, notching an .889 OPS and thriving defensively. But Andújar should be healthy. Does he get his old job back, or is he defensively-challenged at third to the point where the Yankees look to transition him to the outfield or first base?

Deal for Dellin?

The Yankees could've used Dellin Betances in their bullpenning efforts against Houston. But he may have thrown his last pitch in pinstripes since he's heading for free agency.

His injury-plagued season ended with a partially-torn left Achilles as he was trying to pitch himself into form for the playoffs. While Betances profiled as a future closer for another team, perhaps the injury adds uncertainty to his free agency and he comes back, postponing the mega-payday for after he proves he can be as dominant as he's been in the past.

Will Brett jet?

Brett Gardner is a free agent, too, and is coming off a year in which he played more than anticipated because of all the Yankee injuries and blasted a career-best 28 home runs. He could return as a fourth outfielder, which might be fitting for the career-long Yankee. Does whatever the Yankees do with Clint Frazier impact Gardner?

Here's the catch(er)

While Gary Sanchez is often polarizing, at least among Yankee fans, it seems unlikely that he wouldn't be the primary catcher next season. No backstop in baseball has his kind of elite power - he slugged 34 homers in 396 at-bats in 2019. He had shown improvement behind the plate before some glaring October lapses. Backup might be less settled - Austin Romine, who's been terrific in the role, is a free agent. Does he want his own shot as a starter somewhere else? Kyle Higashioka could be Sanchez's backup if Romine departs.

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