Yankees’ Brian Cashman talks free-agent shortstops, Aaron Judge contract, 1st base options, Gary Sanchez’s future | Q&A

NEW YORK — With a sleeping bag tucked over his arm, Yankees general manager Brian Cashman arrived at the Covenant House in Midtown Manhattan around 9 Thursday night to participate in the youth homeless shelter’s annual sleepout for the 11th year in a row.

Braving chilly temperatures and some steady rain, Cashman said, “It’s just one night for me thankfully, but unfortunately it’s every night for a lot of people that don’t deserve it.”

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Before crashing, Cashman held court with a group of Yankees beat writers for more than 30 minutes. Topics addressed included the now-open free agent market. They need a shortstop, and this is the year to get one with many of the best out there for the taking, the likes of Carlos Correa, Corey Seager, Marcus Semien, Javier Baez and Trevor Story.

Cashman also talked about how the Yankees plan to handle Aaron Judge’s contract status, the possibility of a lockout next month plus what the organization’s 2022 plans are for Gary Sanchez, Aaron Hicks, DJ LeMahieu, Joey Gallo and Clint Frazier, among others.

Friday’s 6 p.m. deadline to set the 40-man roster also came out. The Yankees have no openings and five of their top 20 prospects (according to MLB Pipeline) need protected to keep them out of the Rule 5 draft pool. Cashman’s flunked this test last year not protecting two right-handers. Garrett Whitlock had a sensational season pitching to a 1.96 ERA as a Red Sox reliever, while Trevor Stephan had a good rookie season as a Cleveland bullpen piece

The reminders of those mistakes could lead to some Friday wheeling and dealing by Cashman, or perhaps freed-up roster spots via DFAs.

Cashman also broke some coaching-staff news.

Here’s what the GM had to say:

Q: What do have cooking?

Cashman: Obviously, we’ve got some roster issues that we’re staring in the face, so I think the whole industry is up and running dealing with protection lists. At the same time, obviously, there’s free agency and trade conversations that are well above that. I’m trying to finish the coaching stuff. I have some offers out.

Q: Some of the Yankees’ best prospects need to be protected. How many spots do you think you need to open?

Cashman: Like every year, you can’t add all the ones that you feel like you potentially could lose and not get back. We got burned heavily last year in that regard with the same issue. So we have a good strong system. It provides a lot of difficult choices to make. We’ve got a roster that’s got not a lot of flexibility, so we’re trying to create some flexibility. We’ll see if we have any luck in that way. If not, we’ll just have to make some tough decisions. But we do have a lot of dialogue going. There’s been a lot of late nights in the past week especially.

Q: If Zack Britton is not expected back next year (due to September Tommy John surgery), is there anything roster wise that you would do with him (considering he has just one year remaining on his contract)?

Cashman: He has an outside chance to be back. It’s unlikely in my opinion, but not out of the realm of possibility because he’s a reliever.

Q: How many coaching staff positions will you hire (besides new third base coach Luis Rojas)?

Cashman: We have our hitting side. We have first base to fill. And that’s where we’re at currently.

Q: Two or three pitching coaches (counting the bullpen coach)?

Cashman: We’ve always have had two, but there’s an industry movement of adding a third. So I think we’re probably going to wind up that way, as well.

Q: Are you thinking of going with three hitting coaches, too?

Cashman: We’ve definitely looking at doing three pitching coaches, three hitting coaches to allow obviously some specialties to be playing out. We’ll see how it all plays out. I think once that’s in play we’ll have those respected people to address that easier than I can right now. I do have offers out and in some cases I feel kind of settled in on certain people, but I’m not ready to announce anything yet.

Q: Do you want a change in philosophy for hitting or do you think hitters maybe tune out coaches at times and change is good? What’s the thought process?

Cashman: Moving on from Marcus (Thames) and PJ (Pilittere) … it just came down to choosing to either reinvest in the same people we had or obviously bringing in somebody else that we also believe in. There’s a lot of different ways to go about doing things. I said last summer many times I didn’t think our coaching was our problems, and those words were backed up. We never made any changes to our coaching staff (during the season). It just now comes down to game planning as we move forward. What’s the best staff that I feel is going to serve us as we move forward in ‘22 and beyond? That’s what we’re trying to come up with. We certainly have taken notice some teams have had a lot of success by adding a third specialty coach in those categories, whether it’s pitching or hitting or both. And I think we’ve always spoken to the fact that the Yankees should be using every tool in the toolbox to their advantage to benefit our players. And so if adding a third one is going to free up our personnel to do a lot more to try to impact our players in a positive way, then I know our ownership is already all in on that.

Q: Some of the top free agent pitchers already have signed (with Justin Verlander returning to Houston, Noah Syndergaard signing with the Angels and Eduardo Rodriguez signing with the Tigers). How does that affect the Yankees?

Cashman: There has been movement. Pitchers have come off the board, some of them rather quickly. Our starting pitching is strong. I think it’s the strength of our team currently, the way it ended the season. And we’re excited to also have (Luis Severino) coming back into the fold … but that doesn’t preclude us from adding to our rotation, or adding to our bullpen. But obviously our focus still is trying to address the shortstop area more than anything else and explore opportunities on all position levels. If there’s something that’s better than what we already have, let’s see if we can make that fit. So ultimately my job is to find a way to come up with a roster that we feel a lot better about than the one that finished the season. And we liked that roster we finished the season with. We just didn’t like how it played.

Q: How much urgency is there to fill the shortstop position?

Cashman: It’s an urgency. It’s an area that we feel we need to address. How that gets addressed remains to be seen. In a big way, a small way and an acceptable way? We’ll see. Will it be obvious? Will it be subtle? Time will tell.

Q: Do you expect to sign a big free agent before Dec. 1? Is that a deadline (because that’s when the CBA expires and a lockout can begin)?

Cashman: I don’t have a deadline. The most important thing that I can do with our baseball ops team is to try to run into some good, sound baseball decisions. Whether that is a big fish or not remains to be seen. So I am casting a wide net talking to every level of the food chain, the biggest and the baddest as well as the teeny weeny ones, too. As long as it somehow makes us better in our mind, that’s the biggest thing. But I’m open for business. There’s no doubt about that. We’re trying to figure out a way to do some things. We’ve had offers out to the players and to teams, but nothing to show for that.

Q: Will shortstop prospects Oswald Peraza and Anthony Volpe factor in how you address the shortstop opening this winter?

Cashman: They have to. You have some guys that are on the come that you think highly of, so that means they will eventually arrive. So you either make plans for them to hopefully impact you, or ultimately I guess sometimes they could be trade pieces. But you always like to hold on the best of the best if you can. When you have the ability to play shortstop, also you have the ability to move all over. Usually the most athletic person on the field is your shortstop, so that allows them typically to move to third, to second, in some cases the outfield. So we’ll see. We know we have some really good ones coming, but they’re just not ready.

Q: Would you ever talk to a free agent about potentially changing positions in a few seasons?

Cashman: I wouldn’t sign somebody with that intention, saying “If we make this partnership … hey, within a year or two you’re going to have to move whether you like it or not.” No. Because there’s no guarantees the players that you have develop the way you want. All those things sort themselves out. So I wouldn’t foresee having a sit-down conversation with a prospective free agent saying, “Hey, if we do something with you, we need you to move later.”

Q: Are you anticipating a lockout on Dec. 1?

Cashman: As of right now, it’s business as usual for us.

Q: Do you expect to play a full season in 2022?

Cashman: We’re used to 30 years of labor peace, so because of that I expect it’ll be 31 years and beyond. So that’s my optimistic side. You’ve got obviously two really smart sides. One side has a business to run, one side is working the business. I’m optimistic that at some point it’ll all work out like all the previous ones. But it’s above my paygrade. I don’t have a seat at that table, but I know they all want the same thing, which is a highly productive industry where everybody benefits.

Q: With free agents, do you get the sense that they would prefer to wait for a new CBA before signing a deal, or is there an urgency to maybe get things done before a lockout?

Cashman: My impression is free agent are ready to rock and roll. So we’ve made offers and we’ve signed one back, which was (reliever) Joely Rodriguez. So it seems like it’s a swift moving market so far. It feels that way.

Q: Assuming DJ LeMahieu has recovered from his offseason sports hernia surgery by the start of next season, what role do you see for him? Does it depend on what moves are made in the offseason?

Cashman: He can play first. He can play second. He can play third. Same role that’s been in play. It just depends on how this team gets reconfigured. It depends on what we import and how we place our bets. That’s the beauty of DJ LeMahieu. He provides that type of versatility.

Q: Do you anticipate engaging with Aaron Judge’s agents about a long-term contract?

Cashman: We’ll have to have conversations about a one (year) or multi-level deal. We’re essentially a season away from free agency, so we’ll have to have conversations with Aaron Judge’s representation. But obviously he’s been a great Yankee. He’s impacted us in such a positive way for quite a long time, so it’d be nice to keep it going. But we’ll see where it takes us. Those conversations haven’t happened, but they will be happening at some point.

Q: What are your thoughts about first base? Luke Voit is still on the club, Anthony Rizzo is a free agent and there could be some intriguing trade options (such as Oakland’s Matt Olson). Is this an area that you would like to get some clarity quickly?

Cashman: What I want to do quickly is run into some good opportunities that I actually have a chance to close out.

Q: Would you anticipate that status quo a catcher?

Cashman: As of right now, Gary Sanchez and Kyle Higashioka are our catching unless we run into something that we feel can upgrade that and make it better. We are obviously having conversations to see if there’s options. Catching is a very thin market. It was last year, and I can say it looks like it’s that way this year again. But it doesn’t preclude us from exploring potential options that exists out there. And if not, we’ll go back with what we have.

Q: You guys debated internally about tendering Sanchez a contract last year. Did this year change that opinion?

Cashman: He worked his tail off. I thought his catching without a doubt got better, although in the very end he had some struggles that magnified. It was almost like pick the scab and it made everybody remember what it was like in the past. But I think overall he was significantly better at the catching position last year than the prior years, so I’ve got to give him a lot of credit for the hard work and the dedication that he had towards trying to improve because he did improve. But there are certainly some memories of that we all recall, obviously, that kind of clouds that overall judgment of the 162-game season that he put forth, so we obviously have decisions to make as we move forward in terms of trade, tender, all that stuff. We’ll have to see how that all shakes out.

Q: Is the plan still to keep Austin Wells at catcher? Has there been any talk about trying him at other positions?

Cashman: When we drafted him, we knew that the catching was something that he was going to continue to work at. He was drafted (in the first round in 2020) because of his bat. He’s a hitter. He’s a hitter that we hope can catch, but we also knew drafting him that if he couldn’t over the course of time as his journey takes him up the ladder, whether it’s first base or DH, those would be the alternatives for him. But there’s no reason right now yet to believe that he doesn’t have the opportunity or the abilities moving forward to remain at that position, so that’s why he’s still doing it.

Q: What’s the offseason plan for Deivi Garcia (who had a very poor season pitching in Triple-A)?

Cashman: He might do some winter ball, but other than that just reconfigure work with (minor league director of pitching) Sam Briend and his staff. Last year was the first year he struggled. Sometimes that’s the biggest hurdle to get through. The plan is to correct certain things that they believe were part of that problem.

Q: Have you spoken to Brett Gardner? Do you have any clarity if he wants to play next season?

Cashman: I haven’t spoken to Brett at all, but that’s not unusual. I deal with his agents. I had an early conversation. They had the first decision, which is they were not going to exercise the player option, which triggered our decision not to exercise the club option, which created this free agency. We have not in conversation since. They have conveyed that he wants to play.

Q: Aaron Hicks wants to play winter ball after missing most of this year due to wrist surgery. Will there be discussions on that?

Cashman: We’re all in, Our assistant strength coach just saw him out in Arizona, and he looked really good. So he’s obviously working his tail off. He’s in tremendous shape. He’s put himself in a good position. He’s healthy. He’s going to play winter ball in the Dominican in December. We’re looking forward to him knocking some rust off and being ready to go come spring training.

Q: Does this development with Hicks change your opinion about maybe adding a center fielder?

Cashman: No. I just think I need to explore centerfield as a possibility, as well, if there’s things that make sense there for us just because obviously Aaron has had the last number of years of injury. I know the type of player is capable of being when he’s healthy and on the field. He just haven’t been able to stay on the field for us. So we’ll see. It doesn’t mean that he’s not going to be manning that position for 150 of the 162 next year. But I’m going to look at all opportunities to see if anything makes sense.

Q: Is one of the options adding a starting centerfielder and sliding Hicks into a fourth-outfielder role?

Cashman: We’ll see. We’re going to explore all opportunities that might exist. Some might make less sense than others. Clearly outfield is an area of depth without a doubt with us. We have Judge in right. We’ve got (Giancarlo) Stanton and (Joey) Gallo. We’ve got Hicks coming back. So there’s a lot of a lot of high-end talented players with financial commitments, too. So there’s not a lot of room out there. And so in terms of allocating resources, it makes it maybe more difficult to pour more into that arena, but it doesn’t mean we’re not openminded to anything and everything could make sense. Again, I think our biggest focus is going to be shortstop, but at the same time I’m talking to catchers, first base, center field and listening to trade talks on a lot of different players on the roster at the same time.

Q: What’s your thoughts on Joey Gallo going into his first full season with the Yankees?

Cashman: Clearly, he came in and didn’t play as well as he’s capable of playing. It’s not easy transferring over from one city to another. But I believe he’s very talented and I think that his two or three months experience with us will benefit him as he enters his free-agent walk year. He’s a potent left-handed bat with plate discipline and power, and with a Gold Glove-caliber defensive side. So he can provide a lot for us. Hopefully we can tap into that more in ‘22 than we were in the second half of ‘21.

Q: Are you concerned the environment might not be suited for Gallo?

Cashman: I don’t want to say there’s a concern. I just think that he will benefit now from coming on over and having the experiences he had. So I think you’re going to see a much better version of what we saw from him last year. But that’s not saying much. He struggled by his admission, by our admission, by fact. He struggled with us more so than he did with Texas, but he’s a threat every time up at the plate and I would bet that you’re going to see a much improved version of him next year for us. I feel very confident saying that because he’s that talented. So I expect him to be here. I expect to be part of our configuration and someone that Boone will be happy to deploy on a daily basis. But it doesn’t guarantee anything. We’ll explore options. People come asking about players and I’ll be asked about a lot of our guys. If I’m doing it right, I’ll listen. Most of it won’t make sense, but every now and then you run into something that you think does.

Q: Gallo is a career .206 hitter and batted .160 this year for the Yankees. When you say he’s going to be better, do you not care about the batting average because he gets a lot of walks and hits a lot of home runs? Are you good with that, or would you like to see him sacrifice a little power to hit for a higher average and strike out less?

Cashman: I’ll leave that to the coaching side, but the positive side is he provides a lot of plate discipline, which drives pitch counts up. He has a huge amount of walks, so he’s getting on base. How he does that might be different at times, more walks than maybe singles. And he’s got that big power threat every single time. Clearly, he’s got the strikeout component that comes with it. Like anybody who strikes out a lot, if you can cut that down and overall benefit your profile … That’s stuff that he and the hitting coaches can work through along with all our guys in our lineup. Most of our guys got some swing and miss in there that we’d like to tap down to some degree, but you don’t want to tap down something to a level then it changes somebody’s strengths. So that’s the balancing act.

Q: When you were running down the outfielders, you didn’t mention Clint Frazier. Where does he fit in?

Cashman: It remains to be seen. I just mentioned the guys that you’re going to count on starting right now, and he’s not in a starting configuration. He was taking off rather early last year (due his dizziness), and he didn’t get back. So obviously he’s going to have to fight his way back into it. He’s certainly more than capable of doing that. Most important is his health and being healthy. Once that’s in play, which I believe it is, then his journey can begin again.

Q: Has Frazier been cleared for spring training?

Cashman: I think he’s getting there, but I don’t want to say he’s full go yet. I’d be overstepping on that. But he is in Georgia and he is doing some baseball activities.

Q: The Mets announced Billy Eppler was hired as their GM. What do you think of your former assistant being your new competition in town?

Cashman: He’s really good, in my opinion. I got a chance to work alongside him for quite some time. A lot of people look at the general managers as the figureheads, and I’ve been the figurehead here for quite some time, but I’ve been able at staying power because it’s really baseball ops that are the people you surround yourself with. I was lucky to have been surrounded with Billy Eppler for a long time. He impacted us in a really big way and in a real positive way. He’s a great baseball man and I think that the Mets secured a really high-end talent. He’ll serve them well and I’m sure he’ll hire well. So nothing but congrats to him and congrats to the Mets.

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Randy Miller may be reached at rmiller@njadvancemedia.com.