As is custom following the end of the season, Yankees GM Brian Cashman and manager Aaron Boone will hold a press conference on Thursday to reflect this past year and look ahead at plans for the offseason.
There is also the small chance that some news about certain players surfaces as well. Fans may remember the announcement of Didi Gregorius needing Tommy John surgery came in this press conference last season.
So, with many different questions to answer before they jump headfirst into the offseason, here's a few Boone and Cashman should answer on Thursday...
Does Cashman regret not trading for starter?
It isn't the reason why the Yankees ended up losing the ALCS to the Astros. The Yankees couldn't get that timely hit with runners in scoring position all series long, while Houston came up with some clutch homers.
But, at the end of the day, the Yankees rotation was overmatched by the Astros' Big Three in Justin Verlander, Gerrit Cole and Zack Greinke (I just say Greinke's Game 4 start, not Game 1). James Paxton and Masahiro Tanaka went six innings just once this postseason, while Luis Severino only managed to get through 4.1 innings in his longest outing in Game 3 of the ALCS.
When Verlander and Cole were on the mound, many would expect at least seven innings from them, but the same couldn't be said for the Yankees. Cashman didn't like how the market played out at the time of the trade deadline, and in turn, no pitching moves were made to bolster that rotation. It'll be interesting to see what he says.
How active will Cashman be in acquiring that starter in free agency?
To piggyback off the last question, Cashman will now have the opportunity to get his desired starter on the free agent market, and there are some great names to pick from.
Cole will be the biggest free-agent prize this winter, and he could easily become the highest-paid starter in the game. There's also the chance Stephen Strasburg opts out, while Zack Wheeler and Madison Bumgarner will also be out there to pick up.
Whether or not Cashman will want/get the clearance to break out the old Yankee checkbook -- not the recent one that has kept the team under the luxury tax -- is not yet known. And while he shouldn't reveal his budget, Cashman may hint to how aggressive he'll be to add what could be the team's new ace.
Would Boone change any moves made during the ALCS?
Boone had a much improved postseason compared to his first in 2018, where he made a few questionable moves. But the end result -- not making it to the World Series -- is not what he had in mind with a club he, and many others, viewed as better than last year.
His bullpen moves were swift this year, knowing that he could lean on a plethora of arms. It didn't always work out, though, with one prime example being the pull of Chad Green in Game 2 to bring in Adam Ottavino. Green was rolling, but Ottavino came in against George Springer, and he hung a slider that was belted to the train tracks in Minute Maid Park to give the 'Stros the lead.
There wasn't much to critique given how the Yanks played, but getting Boone's perspective on what he might have changed will be telling.
What should be done with Didi Gregorius?
Gregorius is an unrestricted free agent now, and the Yankees will need to make a decision on what they want to do. He came back midway through the season after recovering from his surgery, and produced modest numbers. He also had a so-so postseason at the plate.
Gregorius is a sure glove at shortstop, and his leadership qualities in the clubhouse are highly valued in the Bronx. But with Gleyber Torres' star status continuing to rise after another outstanding season, and DJ LeMahieu emerging as the Yankees' MVP this season, Cashmnan would very well let Gregorius test the market and move on. Torres could slide to shortstop while LeMahieu gets his everyday role at second base.
Gregorius was more than just Derek Jeter's replacement these past few years, and Yankees fans are certainly grateful for that. But is his time over in New York?
What about Dellin Betances and Brett Gardner?
Both of these Yankees vets are hitting free agency, so Cashman will need to figure out if they're returning as well.
Betances returned to the Yanks late in the season, and after a stellar inning of work against Toronto, it looked like he was going to be another solid addition to the bullpen. But then it was revealed that he actually tore his Achilles during that outing, a terrible announcement after all the rehab he went through to return to the team in the first place.
His injury history is extensive, so we'll see what the Yankees will be thinking about with an already stacked bullpen in the first place.
As for Gardner, he can remain the longest tenured Yankee once again if he returns. He also showed off great power numbers this season at age 36. The Yankees, though, have Cameron Maybin who broke out this season. And until they decide to trade him, Clint Frazier's bat in the minors remains a depth option as well.
What does Boone believe these Yankees need to improve on to return to World Series?
This was supposed to be the year the Yankees got back into the October Classic. Instead, this became the first decade in a long time that the Yankees didn't make it at least once.
So what will it take for them to get back to the World Series next season? Boone should answer that question after taking the time to look back at the postseason. As we mentioned, getting those timely hits was a big issue for the Yankees -- a team that led the MLB in average with runners in scoring position during the regular season this year.
The Bombers have everything in place to run the tables in the AL East again next season, and Cashman should find ways to improve things as well. But looking further ahead to Spring Training, Boone may have in mind what he wants to see this team improve on to make sure that sour taste they have in their mouths right now doesn't happen again.