NEW YORK -- Brian Cashman occupied the chair at the front of the Yankees’ press conference room for 42 minutes on Oct. 24, then passed the microphone to Aaron Boone, whose postmortem remarks recapping the 2019 season lasted 23 minutes.

It was an appropriate allocation: With the offseason underway at Yankee Stadium, the manager’s work is largely complete. The next several months will belong to the general manager and his staff, and when Cashman makes his recommendations to ownership, he says that he plans to be blunt in evaluating the strengths and weaknesses of a roster that fell six victories shy of its objective.

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“I am not afraid to admit this was a great team,” Cashman said. “I’m not afraid to acknowledge that we went up against a great team in Houston. I think it's very important not to get emotional. It’s very important to be reflective on areas that you can get better at, and be objective and acknowledge the areas that you've been really good at and excel at.

“I can just tell you that I'm proud of all of the personnel we have and what we've done to put ourselves in a position to take our shot. I’m disappointed that, at least in 2019, it wasn't enough.”

Which players are free agents?
The Yankees’ free agents include right-hander Dellin Betances, outfielder Brett Gardner, right-hander Cory Gearrin, shortstop Didi Gregorius, outfielder Cameron Maybin, catcher Austin Romine and designated hitter Edwin Encarnación.

Are any of them likely to receive qualifying offers, and when would they have to make that decision?
Gregorius is a candidate to receive a qualifying offer, valued at one year and $17.8 million. That represents a raise over the $11.75 million that Gregorius earned in his injury-shortened 2019, when he returned from Tommy John surgery to bat .238/.276/.441 with 16 homers and 61 RBIs in 82 games (87 OPS+).

Should the Yankees make that offer, it would create an avenue for Draft compensation if Gregorius signs elsewhere. Gregorius, 29, has said that he hopes to continue playing with the Yankees, though he may test the market in search of a multiyear deal. The deadline to make a qualifying offer is Monday.

Which free agents are most likely to come back?
Given the news that Aaron Hicks has undergone Tommy John surgery on his injured right elbow, the Yankees must determine the identity of their Opening Day center fielder. That could open the door for Gardner’s return, especially if the 36-year-old remains open to a one-year contract like the one he signed last November for $7.5 million.

Gardner enjoyed a career year, batting .251/.325/.503 with a career-high 28 home runs and 74 RBIs in 141 games (117 OPS+), playing above-average defense in left field and center field. The longest-tenured Yankee, Gardner said that he hopes to continue his career in the Bronx, and Cashman said that he believes Gardner would be capable of handling regular playing time in center field again.

Betances presents an interesting case, having lost almost all of 2019 to injuries after establishing himself as one of the better relief pitchers in the game. This represents the 31-year-old Betances’ first crack at free agency, and the four-time All-Star could have a long memory after a contentious arbitration battle with the club in '17.

Which players have options, what’s the dollar figure and impact on payroll, and when does it need to be decided upon?
The Yankees declined Encarnación's $20 million option on Halloween and opted to pay the slugger a $5 million buyout as part of his contract. Left-hander Aroldis Chapman, who could have opted out of the remaining two years and $30 million on his contract, instead reportedly will remain with the Yankees through 2022 after reworking his deal.

Who might be a non-tender candidate, and when does the club have to make that decision?
Greg Bird once said that he would probably have “five, six, seven thousand more chances” at the plate in big league games, but those opportunities are growing scarce for the first baseman, who has been unable to remain healthy for a full season. Bird, who turns 27 in November, is currently playing in the Dominican Winter League after being limited to 10 games this season by a torn left plantar fascia.

Bird earned $1.2 million this past season, making him a strong non-tender candidate as he approaches his second year of arbitration eligibility. Another candidate could be left-hander Tyler Lyons, though Boone said that Lyons opened eyes with a solid September, leading to his inclusion on the postseason rosters.

New York’s other arbitration-eligible players are right-hander Chad Green, right-hander Jonathan Holder, right-hander Tommy Kahnle, outfielder Aaron Judge, left-hander Jordan Montgomery, left-hander James Paxton and catcher Gary Sánchez. The Yankees must tender offers to arbitration-eligible players by Dec. 2.

What kind of help do they need and will they be active in free agency? Who might they target?
Cashman believes that the Yankees had “a championship caliber team” in 2019, one that had a legitimate chance of bringing home the franchise’s 28th World Series championship. They won 103 games in the regular season, securing their first American League East title in seven years, and were one of the final three teams standing. With that, it’s believed that any upgrades could be incremental.

Right-hander Gerrit Cole is the obvious target to discuss, and the Yankees have tried for his services twice before, making him their first-round Draft selection in 2008 (he attended UCLA instead) and attempting to trade for him prior to the '18 season (the Pirates liked the Astros’ package better).

As the premier free agent of the offseason, Cole, 29, projects to land a mega-deal in the ballpark of seven years and $250 million. Does that fit into the Yankees’ budget? And, if the money is equal, would the Southern California product prefer New York over the Angels or Dodgers?

Other starting pitchers available via free agency could include Stephen Strasburg (if he opts out of his contract), Madison Bumgarner, Hyun-Jin Ryu, Jake Odorizzi, Dallas Keuchel and Zack Wheeler.

Since the Yankees seem set at the infield spots (a Gregorius departure would present an opportunity to make Gleyber Torres and DJ LeMahieu the double-play combination), their other winter focus could be on the outfield. Re-signing Gardner is the likely avenue, though other potential free agents capable of playing center field could include Starling Marte, Jarrod Dyson, Billy Hamilton and Juan Lagares.

Don’t rule out the Yankees looking to bolster their bullpen. The crop of free-agent relievers include Will Smith, Will Harris and Sergio Romo.