Nearly two weeks into free agency, the Cubs still haven’t signed anyone. They protected some prospects from next month’s Rule 5 Draft, claimed a pair of infielders off waivers and made decisions on whether or not to tender contracts to their own players, but they haven’t yet made a play on the free-agent market.

With so little movement in free agency, Cubs fans have questions about this winter — and CHGO is here to answer some of them. Inside this mailbag, we discuss potential free-agent targets, in-house candidates for extensions, whether or not offering eight-plus-year deals is smart and more.

Questions have been edited for length and clarity.

MattGregory asks: If Nico Hoerner and Nick Madrigal are starting up the middle for the Cubs in 2023, is the offseason a disappointment?

It would be hard to call it a disappointment without knowing what moves the Cubs make instead. Hoerner proved to be a very good option at shortstop, and I think Madrigal’s defense at second base is a little underrated. So, I don’t think that’s a worst-case scenario.

But certainly, any of those big-name shortstops would check off multiple boxes on the offseason to-do list, and not being able to add one of them would be a big hit to the prospects of being competitive next season. Plus, Madrigal has spent more time on the injured list than on the field since the Cubs acquired him at the 2021 trade deadline, so there’s really no guarantee a starting middle infield of him and Hoerner will even last the whole season.

Look, I don’t even need to say at this point that the Cubs would be a perfect match for one of the four shortstops. It makes all the sense in the world for them be major players in that part of the market. So, would it be a disappointment if they don’t land one? I can’t say that for sure, just because there are plenty of moves the Cubs could make that would fill other holes and make this offseason feel like a success. Still, signing one of the shortstops would be the best way to ensure this winter isn’t a disappointment.

Snewbanks31 asks: Do you think Jed Hoyer and Co. try to lock up the younger guys rather than allow them to reach free agency or deal them like they did with the last core?

pham_910 asks: What, if any, are foreseeable hindrances in signing Ian Happ or Nico Hoerner?

As Hoyer said during his end-of-season press conference last month, the Cubs are looking to extend some of their current players.

“I’d say that we’ve taken the first steps,” Hoyer said. “As you guys know, we’re not going to talk about it once we do, but certainly there are players that we’d love to keep in a Cub uniform for a long time. Hopefully, we can work hard on those and get some across the finish line.”

He was asked specifically about Hoerner and Happ, and those are certainly two big candidates for extensions after the seasons they put together in 2022, but you could also make a case for players like Justin Steele or Keegan Thompson. One of the biggest criticisms aimed at the front office during the last rebuilding cycle was the inability to sign any of the young core players to extensions, and that chapter officially closed when Willson Contreras hit free agency. The Cubs did enter extension talks with them at various points, but this time around, it feels like they might actually get to the finish line.

As far as hindrances go, I can’t see anything stopping the Cubs from doing what they can to resign Hoerner. He won’t be 26 until May, the Cubs still have three more years of team control and his up-the-middle defense is going to be even more important moving forward. He’s an easy candidate for an extension.

As for Happ, that’ll be a little more complicated. The Cubs were impressed with what he did in 2022 and believe in the improvements he made both in the field and at the plate. Still, he was involved in trade rumors at the deadline and is now entering his last year of arbitration. He’s made his desire to remain a Cub known multiple times, but it’s tougher to determine if the Cubs want to keep him around long-term.

Dead Gecko asks: Realistically, who should the Cubs mark as their No. 1 offseason get (and why is it Shohei Ohtani)?

Well, at this point, it’s not Ohtani. If the Cubs make a play for him, the more realistic scenario is they do it in free agency next offseason (assuming he doesn’t sign an extension by then).

To me, the No. 1 offseason get would have to be one of the “Big Four” shortstops. The Cubs should certainly look to add one of Carlos Correa, Trea Turner, Xander Bogaerts or Dansby Swanson. Last week, I posed the question of if the Cubs would actually pony up the kind of deal necessary to get one of them, though I believe they absolutely should.

As far as the No. 1 option from that group, if I were running things, Correa would be my target. He’s had some injury issues through his career, but he’s played 148 and 136 games in the last two seasons, respectively. He’s also posted a wRC+ of 123 or above in six of his eight total seasons, and he’s recorded at least three defensive runs saved every year since he made his debut. He’s a great player on both sides of the ball, and at 28 years old, he would be an important addition toward building a competitive roster now and in the future. If it were up to me, he’d be the No. 1 target of the offseason.

moore2score asks: Where do you fall on the long-term-deal conversation? Is it smart to stay away from the eight-plus-year deals stars are looking for, or are they something organizations like the Cubs should be willing to offer?

That’s somewhat a tough question to answer. Obviously, there are very recent examples (i.e. Jason Heyward’s eight-year deal) of long-term deals hampering a team’s ability to make other moves. But I’ve posed the question on the CHGO Cubs podcast before: How would you feel about an eight-year contract that absolutely worked out for the first five years but maybe not so much for the last three?

Say Heyward gave the Cubs five years of All-Star-level play before he started to decline in year six. Would you feel better about that contract? Would it feel more like he earned most of the money he was paid, since most of his contract was spent playing at a high level at the time the Cubs were looking to build a dynasty?

It’s the same for a player like Carlos Correa. Say he signs an eight-year deal with the Cubs this winter. If his first five years are All-Star-caliber years, and then he tapers off some over the last three, is that still a successful deal? I’d argue it would be.

All that is to say, I don’t think the Cubs should shy away from those kinds of contracts. They shouldn’t let the deals that didn’t work out stop them from signing really good players on long-term pacts in the future. There’s risk involved, of course, but to me, that’s not an excuse to not try and sign star players.

MattGregory asks: Do you believe the Cubs will struggle to sign the big-name Scott Boras guys because of their past poor negotiations with his clients?

Honestly, I don’t think that will have much of an impact. Boras is all about getting his clients the best deals he can. If those are being offered by the Cubs, he’ll listen. Money talks, after all.

Mcbaken asks: Which big-name free agents have the Cubs been linked to?

The Cubs have been linked to a laundry list of free agents. That begins with the “Big Four” shortstops, each of whom have been involved in various rumors with the club. You’ve also got Kodai Senga, the pitcher coming over from Japan, who’s rumored involvement with the Cubs hasn’t been nearly as strong but who does still have connections that could keep the team involved in the sweepstakes until the end. And if you want to include names such as José Abreu, Josh Bell or Cody Bellinger as “big names,” the Cubs have been linked to them, too.

Pooch7171 asks: Which relievers do you think the Cubs should be looking at from the free-agent market?

This is probably the area of need the Cubs will have the easiest time addressing this offseason. We know how much success they’ve had bringing in veteran relievers on cheap, short-term deals the last few seasons. There’s no reason to believe they can’t find a couple more this offseason who they can help find some of that fountain of youth.

There are plenty of free-agent relievers the Cubs could be looking at. They could reunite with David Robertson or Chris Martin, who both pitched well in high-leverage spots this past season before being traded at the deadline. Reunions with other former Cubs like Craig Kimbrel or Andrew Chafin could happen. Kenley Jansen is one of the bigger relief pitching names on the market, and coming off a 1.1-fWAR, 41-save season with the Braves, he could provide tremendous value in the back end of the bullpen. There are a lot of relievers on the market, and the Cubs should be able to find some good ones.

Cody Delmendo asks: Will Luke ever be able to learn how to use Discord?

I can answer that in one word: No.

I can also answer that in Spanish: No.

Author

Chicago Cubs beat reporter and podcaster for CHGO. I've previously covered MLB for MLB.com and a bunch of other sports for a bunch of other outlets. Follow me on Twitter @ryan_a_herrera

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