Let’s address the obvious elephant in the room: Do you see senior vice president and general manager Brian Cashman being aggressive enough to pursue Gerrit Cole?
-- Marcus B., Germany

That is indeed the top question at this stage of the Yankees’ still-too-fresh offseason. Cole has work to do yet, beginning with his Game 1 start in the World Series, so I would presume he isn’t giving much thought to his pending free agency at the moment. Even so, the interested teams certainly are -- a group that is said to include the Angels and Dodgers, as well as the Astros.

Cashman and the Yankees will hold their organizational scouting meetings shortly at Yankee Stadium, and Cole will almost certainly appear at the top of their rankings. With agent Scott Boras essentially able to have Cole set the free-agent pitching market, we shouldn’t expect a quick resolution to his free agency.

The Yankees have seemed reluctant to commit big money to starting pitching in recent years: Remember, Patrick Corbin was thought to be a near-lock last offseason when he visited Yankee Stadium, but he found a six-year deal instead with the Nationals. New York hasn't landed the top available arm on the market since Masahiro Tanaka signed his $155 million deal prior to the 2014 season.

Then again, giving the biggest free-agent contract to a pitcher translated into a World Series championship in 2009, when Cashman dropped $161 million on CC Sabathia’s doorstep. A huge part of this will be to find out what Cole wants; the Yankees made him their first-round Draft pick in 2008, but he went to college instead. Cole could opt to play closer to his Southern California home, or it’s possible that he’ll voice a preference to stay in Houston.

If Cole and the Yankees are once again not a match, the rest of the starting pitching wish-list will include Stephen Strasburg, Madison Bumgarner, Hyun-Jin Ryu, Jake Odorizzi, Dallas Keuchel and Zack Wheeler.

What is the likelihood that Didi Gregorius returns as the Yankees' shortstop? If not, are the Yanks confident in Gleyber Torres' ability to play shortstop for the long term?
-- Deric W.

Gregorius has been a terrific Yankee, a fan favorite who deserves tons of credit for almost seamlessly handling the transition from the Derek Jeter era at shortstop. He also said in the wake of the American League Championship Series loss that he would like to stay in New York.

That said, Gregorius’ asking price may prove to be too high for the club’s liking, as he’ll be seeking a multi-year deal with a significant raise from the $11.75 million that he earned in 2019. Gregorius is a candidate to receive a qualifying offer, valued at $17.8 million. If it comes down to Gregorius or a starting pitcher, the Yanks will probably want to spend on the arm, especially if it’s Cole.

There would be a dropoff defensively from Gregorius to Torres at shortstop, but given that Torres is still developing -- maybe you’ve heard, he’s only 22 years old -- there is room for improvement. Having DJ LeMahieu as the everyday second baseman would give the Yankees a tight middle infield, freeing first base for Luke Voit’s return.

Why did the offense change its approach so much in the playoffs? I get that it is the best pitching and all, but during the regular season, the team seemed more balanced.
-- Frank B., New Jersey

Indeed, the “savages in the box” mindset seemed to disappear during the ALCS, or at least it was significantly disrupted by the Astros’ pitching staff. Former big league pitcher CJ Nitkowski found this terrific stat: the Yankees’ 55.8 percent “chase rate” in Game 5 of the ALCS -- that is, chasing pitches out of the strike zone -- was the highest by any club in the 4,932 games played this season.

That was a game the Yankees won, 4-1, thanks in large part to Aaron Hicks’ three-run homer off the right-field foul pole. Were too many of the Yanks trying to be the big-swinging hero? Manager Aaron Boone said all year that he believed homers would win in October, and he was frequently riled when a questioner suggested that more of a "small-ball approach" was required to be the last team standing.

“If we don't win the World Series, it will be driven that we relied too much on the homer,” Boone said on Sept. 18. “In reality, you need to pitch well and prevent runs, control the strike zone and when you get a mistake, knock the you-know-what out of it.

“The team that ends up winning the World Series will do a good job of holding offenses down, and they'll probably hit a lot of balls in the seats when they have traffic to create some big innings off elite pitchers. It's hard to string hits together, game in and game out, in the postseason.”

Where do you think Miguel Andújar fits with the current lineup? Gio Urshela stays at third base, right?
-- Daniel B., Galva, Iowa

The Yankees believe that Andújar will be able to return as the same caliber of player who finished second in the AL Rookie of the Year Award voting in 2018, but given Urshela’s surprising level of play on both sides of the ball, third base would appear to be Urshela’s job to lose going into next spring.

It’s incredible that the Yankees somehow found a player of Urshela’s caliber for the price of a mid-level sport utility vehicle ($25,000). They viewed him as a strong defender who would provide organizational depth, but they never could have predicted he’d be their third-best offensive player (133 OPS+, behind only Aaron Judge’s 143 and DJ LeMahieu’s 136).

One factor to consider is that Major League rosters will expand to 26 players next season, which could provide the opportunity for the Yankees to carry both Andújar and Urshela if they so desire.

Will the Yankees make any changes to their medical or training staff this offseason? Shouldn’t they?
-- Terry B., New York

Now that the season is over, the Yankees will execute a deep dive into the underlying reasons behind having a Major League-record 30 players on the injured list (39 stints), and it is likely that some changes will be made.

Some of the injuries were unavoidable, like Edwin Encarnación getting hit in the right wrist by a pitch in August, but the more concerning occurrences should be the players who were already rehabbing injuries and then were hurt again (Luis Severino and Dellin Betances, most prominently). Managing general partner Hal Steinbrenner said that the club was investigating those as far back as May.

“We’ll wait until all the data is in and at the end of the year, if we need to make changes in procedures and the ways we do things, then we’re going to do that,” Steinbrenner said in June. “There’s no smoking gun right now. It would be easier if there was, but we’re looking at everything intensely, and any time we have a year like this, we’re going to do that.”