Welcome in to the first Cubs mailbag of the 2024-25 offseason! We answered a wide array of questions ranging from free agency thoughts, possible trade options, a 2016 documentary, favorite offseason hobbies and more.

Thank you to all for the submissions and please keep the questions coming! We will be answering more mailbag inquiries on the Cubs Weekly Podcast set to be released Thursday, Nov. 14 and we plan to have several mailbags a month throughout the offseason.

MORE FROM THE 2024 GM MEETINGS
– How the Cubs view the catching position as offseason kicks off
– Cubs legend Kyle Hendricks close to joining Angels
– Jed Hoyer breaks down some of the Cubs first moves of the offseason
– Cubs feel optimistic despite uncertainty surrounding Ben Brown
– How Cubs might pivot if Nico Hoerner isn’t ready to go by Opening Day
– The ripple effects of Cody Bellinger’s return to Cubs in 2025
– Cubs begin offseason by reuniting with member of 2016 squad

What is in your opinion the most important factor in this years free agency? – @itsnoahbyrd

Andy Martínez: It’s not specified whether it’s for a player or the Cubs, so we’ll answer for both. For a player it’s what it’s always been — the best deal and fit for him. Players almost always will sign the biggest deal. But they also want to be comfortable. Where is Spring Training? How committed is the team to trying to win? How does the organization treat their players? All those things matter.

For the Cubs, it’s very similar — who is the best fit? They won’t be shopping in the upper tiers of the free agent market (i.e. Juan Soto or Corbin Burnes) but the Cubs have found success lately without signing the cream of the crop in free agency. Jameson Taillon, Dansby Swanson, Seiya Suzuki and Shota Imanaga haven’t necessarily been the biggest names available, but all have been solid contributors for the Cubs over the last three years.

What free agent pitcher do you think the Cubs will realistically pursue and acquire? – @nikolasmelendez
Any free agent pitchers or trades for pitchers? – ian_martens44
Will the Cubs pick up a starter this offseason? – wrigleyville_coverage

AM: The last one is the simplest to answer: yes, the Cubs will add a starter this offseason. They need starting pitching. Their rotation currently consists of Justin Steele, Imanaga, Taillon and Javier Assad. Jordan Wicks, Ben Brown and Hayden Wesneski will be in the mix and make starts for the Cubs in 2025, but you can’t count on them in the rotation after their injury history, so yes, the Cubs will add depth.

Trying to predict who they will acquire is difficult. Free agency is wild and unpredictable. So, we’ll give some names of pitchers they could pursue.

The last two offseasons, the Cubs have signed starters that project well and may not be the flashiest name. Taillon and Imanaga weren’t the pitchers with the most pizzazz, but they’ve been integral pieces to the Cubs starting pitching success the last two years. Burnes won’t be donning Cubs pinstripes next year, but you could make an argument someone like Max Fried has been just as solid, isn’t as buzzworthy, but would still produce good, front-of-the-rotation type stuff. Fried has the qualifying offer attached to him and it comes at a hefty price (forfeiting their second- and fifth-highest draft picks next year and $1 million in international bonus pool for the upcoming signing period).

Walker Buehler is an interesting name, too. In September, you could have seen him as the type to sign a one-year pillow contract, similar to the one that Cody Bellinger signed with the Cubs prior to 2023. His postseason — especially his World Series — might have changed that thinking. When he’s healthy, he has front-of-the-rotation type stuff, he clearly has playoff mettle and he was college teammates with Dansby Swanson. OK, that last one might not matter, but it was worth pointing out!

[WATCH: 1-on-1 with Hoyer on Day 3 of the GM Meetings]

Nathan Eovaldi has past playoff pedigree, too, and would be a fit. Blake Snell is a two-time Cy Young Award winner, but he’s been inconsistent throughout his career and doesn’t quite fit the mold of past signings like Taillon and Imanaga.

The trade market is difficult to predict. It’s not easy to line up perfectly on deals with other teams, but it’s an area that the Cubs will pursue to add starting pitching. The Cubs have stockpiled prospects that are now hitting the upper levels of the minor leagues. It could be the perfect time to use that currency to bolster their rotation.

Catcher seems to most likely place to sign a bat, who are the Cubs looking at to sign? – @ty_n_wrigs

AM: The Cubs will sign a catcher, no doubt. Currently Miguel Amaya is the only catcher on the 40-man roster, so another will be added.

In a perfect world, the Cubs add a veteran catcher that can split the catching duties with the Panamanian backstop. Amaya had success at the plate from July 7 on, when he dropped his leg kick for a toe tap. But the Cubs want to add another veteran option that can get Amaya off his feet and allow them to match up better against opponents. It’s the plan they had with Yan Gomes and Amaya going into 2024, but Gomes struggles never really allowed that to materialize.

There are plenty of intriguing names that could be fits in that department. Travis d’Arnaud won a World Series with Atlanta in 2021 and was still a solid contributor in 2024. Danny Jansen is another player in that similar mold, too.

After the Netflix documentary about the 2004 Red Sox, will they do one for the 2016 Cubs next? – @jordan__riddle

AM: There will be documentaries done on that team, absolutely. When that is, who knows? Amazon Prime recently did a documentary on Game 7s that featured the 2016 World Series. But a full documentary on that team would be phenomenal.

Part of what made the Red Sox documentary so special was the candidness that players and front office members spoke with, especially since it’s been 20 years. Many of the players from the 2016 run are still active, so maybe for the 10th or 15th anniversary we could see it? Whenever that happens, it’s going to be must-see TV.

Favorite offseason activity? – @pmthing

AM: I can’t speak for Tony, but for me it’s building Legos and cooking. Porter Hodge and I spoke near the end of the year about our shared enthusiasm on Legos — he had a big F1 car set at his locker. Last year, the Santiago Bernabéu Stadium was my big project. It’s fun to cook new things, too. A year ago I really mastered beef bourgenoine. Send me any recommendations this offseason!

Tony Andracki: As cheesy as it sounds, my favorite offseason activity is being home every night to see my daughter. I love this job but this schedule is a grind, for sure. Beyond that, I get really into the NFL and fantasy football. I have 6 fantasy teams and a few of them are doing well. Don’t ask me how my Marquee team is doing (yes, I took Christian McCaffrey 1st overall).

Are you guys pushing for Max Fried or Logan O’Hoppe in the offseason? – @caidendawg07

TA: To be clear: We are not pushing for anybody. But both players would certainly improve the Cubs’ roster in 2025.

Andy wrote about Fried earlier this week as he took a bigger-picture view on the Cubs’ rotation plans this offseason. The veteran lefty has had a ton of success throughout his career with a 3.07 ERA, a sparkling 73-36 record, 2 All-Star nods, 3 Gold Gloves and a pair of Top 5 finishes in NL Cy Young voting.

That doesn’t mean he is without question marks, however. Fried will be 31 in January and has dealt with some forearm issues over the past couple of years and as a result, has only made 30 starts or topped 170 innings in a season twice in his career. There’s also the fact that he is a lefty. Since the Cubs already have Steele and Imanaga under team control for several more seasons, how left-handed do they want to be with their rotation? Especially when young southpaw Wicks is an option as rotation depth.

[MORE: Kyle Hendricks leaves a lasting legacy in Chicago]

It may come down to the market for Fried and what he is looking for. Will the Cubs meet the asking price? Like Andy mentioned above, any team signing Fried would also have to give up draft pick compensation, so that is another factor to take into account.

As for O’Hoppe, it remains to be seen if he will truly be available on the trade market. At 24, he just wrapped up his 2nd MLB season and is under team control through at least 2028. Teams don’t simply give up on players like that.

Especially when you pair that all with his production. O’Hoppe notched 2.7 WAR for the Angels last year with 20 homers, 56 RBI and a .712 OPS in addition to solid defense.

Like with Fried, the question becomes: What is the cost? The Cubs have prospects to deal (more on that later) and O’Hoppe would represent an upgrade at catcher immediately and in the long-term. If he becomes available, the Cubs should absolutely be among the teams contacting the Angels.

IF/OF seems set but what about Matt Shaw and Owen Caissie? Are they trade pieces? – @stephen.waniewski

TA: I agree, Stephen, the Cubs’ position player group is pretty set. And that means prospects like Shaw, Caissie, Alexander Canario, Kevin Alcántara, Luis Vázquez and others are blocked at the moment.

Injuries could always strike and the Cubs will want to have depth at all levels of the organization — whether that depth is made up of top prospects or veterans with MLB experience. It’s possible the Cubs could make a big trade this offseason — I’ve been thinking for several years now that one is coming eventually. They have plenty of prospect capital to trade away that could help improve the big-league roster immediately.

My hunch is neither of the two players you specifically mentioned will be traded away this winter. Cody Bellinger could opt out again after 2025 while Ian Happ, Nico Hoerner and Seiya Suzuki are only signed for 2 more seasons (through 2026).

Plus, you never know when injuries happen or players slump. Michael Busch had a strong rookie season but he doesn’t have a long track record. Suzuki was benched after a prolonged slump as recently as August 2023. Things change quickly in this game.

The Cubs love Shaw and Caissie and they both had stellar 2024 seasons in the minor leagues. They are certainly knocking at the door of the big leagues and may eventually force the issue and make it so the team has no choice but to find a way to give them playing time in the big leagues.

Can I have free szn tickets? – @_esmeezy

TA: Nope.

Next question!

When do 2025 tickets go on sale? – @enzosdead

TA: You can purchase season ticket plans for 2025 now at Cubs.com.

As for single game tickets, I am not sure the exact date they will go on sale but stay tuned to Cubs social media channels and the team website.

Creed or Nickelback? – anchor_point_blacksmithing

TA: You asked our buddy, Scott Bair, that on the Bears mailbag! I will choose a similar answer — neither. I don’t listen to either band but I will say, College Tony had “Far Away” by Nickelback on his iPod Nano back in the day…

AM: Neither, I choose Rage Against the Machine.

Check out our Bears mailbag each week with Insider Scott Bair.