Jed Hoyer and Carter Hawkins took questions from fans Saturday morning at Cubs Con

The first appearance of Jed Hoyer and Carter Hawkins at Cubs Convention wasn’t their panel on Saturday morning, it was at Ryan Dempster’s recording of “Off the Mound” on Marquee Sports Network Friday night. What was striking about Dempster’s interview was the decision to frame the 2023 offseason as a series of wins. That the Cubs front office had somehow navigated a masterful offseason, where all of their targets signed with the Cubs.

The problem is that just isn’t reality. The Cubs missed on their primary catcher target, Christian Vázquez, who wound up signing a deal similar to the Cubs offer with the Minnesota Twins. They did get Dansby Swanson, but were certainly linked to at least two of the other top shortstops that many analysts (and the contracts that those players signed) thought projected better. They were not close on José Abreu, who I think we can all agree would be a better 1B/DH option to back up Matt Mervis than Eric Hosmer.

And look, I love Dempster, but his late night talk show isn’t exactly 60 Minutes. So it’s not like I expected tough questions about the team’s decision to part ways with Willson Contreras, who signed an eminently reasonable five-year, $87 million contract with the St. Louis Cardinals. However, it was an interesting frame to take into the Saturday morning front office panel. The message the Cubs wanted to send to fans attending the convention was clear Friday night: this was a great offseason, we’ve spent lots of money, fans should be psyched. It’s not a message I, or many of the fans I spoke with this weekend, are fully on board with.

I was thankful that Saturday morning’s panel was moderated by Jon “Boog” Sciambi, who is probably the toughest interviewer of the moderators employed by the Cubs this weekend. Boog not only asked some tough questions, but made sure the front office answered tough questions from fans. The panel began with Boog getting Jed and Carter to promise they would take a call on stage if they got one during the interview to loud applause from a sizeable crowd.

Boog then transitioned to the Dansby Swanson, Cody Bellinger and Jameson Taillon signings, which provided some insight into the process the front office uses to identify and recruit players. Credit where it’s due, I was impressed that they clearly use a lot of empathy to reach out to their preferred targets, noting how their personal experiences informed their pitch to Swanson as he was getting married, or sending Director of Pitching Craig Breslow to “nerd out” with Taillon on pitching infrastructure and how they felt the Cubs could get him to the next level. Hoyer talked a bit more about the pitch lab and how it’s an individualized program focused on each player.

When asked about the makeup of the rotation, Jed specified what we all know. This rotation doesn’t strike out a lot of guys and if you don’t have a lot of strikeouts, you need excellent defense. While I’ve been pretty critical of some of the Cubs offseason moves, they have improved their defense considerably.

They shifted to a discussion of rule changes, which will include the pitch clock, new shift restrictions, larger bases and more. Most of these answers were pretty boilerplate, but there was an interesting back and forth about the bases. Boog asked about what he called “the pizza box bases” (it’s the first time I’ve heard them called that) and if it was a Theo Epstein idea originally. Jed noted that former Cubs front office executive Jeff Greenberg was the first person to throw out the idea but that Theo has championed it at every level. Hoyer also explained that the larger bags should create a safer environment for players, allowing more space to avoid collisions.

There was a shift at this point to spending and player extensions. I thought some of the most challenging questions, along with the most interesting answers, came during this period.

Boog started by asking how often Jed speaks to Tom Ricketts and how frequently those conversations are about the budget. Jed said they speak three or four times a week, but conversations are often extended. What might start as a pop-in for a minute or two often goes 30 min or more. Jed notes, appreciatively, that Tom is very involved. He asks about the draft, scouting, the finer details of baseball operations, but “still lets us do our job.”

The panel transitioned to fan questions, and the fans did not disappoint, beginning with a question from Paul Dzien, better known as Crawly, about a possible extension for Ian Happ given the depth of outfield talent in the minor leagues. Jed noted that avoiding arbitration with Happ was a positive development. The team agreed to a one year, $10.85 million deal before Friday’s deadline:

Hoyer reiterated they never talk about extensions publicly, but have met with Happ’s agents. However, there was no commitment to extending Happ either way. Hoyer discussed depth as a great thing for a team. Despite it being a a bit of a difficult puzzle to put together, having too many players at any position is good, not a problem.

A fan after my own heart then asked about Willson Contreras, and why the three-time All Star starting catcher wasn’t extended by the Cubs and was instead signed by the St. Louis Cardinals. Jed said they were in constant communication with Contreras and appreciated what he did for the team, especially in the 2016 World Series. He portrayed their relationship as cordial, but said the front office has to make hard decisions and were never aligned with Contreras. Credit to Jed for being a bit cheeky by adding he doesn’t wish Willson luck, since he’s a Cardinal. That got a laugh from fans, but the hits kept coming in terms of hard questions.

Questions like why Anthony Rizzo, clearly the heart and soul of the Cubs, was not re-signed this offseason. Jed leaned into emotions here and explained that he knows Rizzo and his family as well as anyone. His son has Rizzo posters on his wall. Jed stated: “In this job I needed to make long-term decisions that were best for the organization. Given where we were in 2021 and what we needed for our future I made the really hard decision to make those trades. It wasn’t easy, but I feel strongly it was right.” Hawkins echoed this about the entirety of the World Series core, who he saw up close when he was with Cleveland in 2016 and he understands how much those players meant to Cubs fans.

Boog followed up with a difficult question that perfectly summed up my feelings about the lack of extensions for the core asking Jed: “I understand you want to win, but surely you get that fans want the band back, they don’t just want to win again, they want to win with Bryant, Báez and Rizzo.” Hoyer’s answer was (paraphrasing): You have to sit with it just like everyone in this room. He noted that some of his best experiences in life were with that (2016) World Series core. He candidly admitted there are very few things he’s more proud of than winning with that group. But he continued that the Cubs were at this crossroads as an organization and the right thing to do was to figure out how to do it again. The right thing to do was to build it again. It will feel really good to get back and fill up Wrigley every year with a young exciting team. Hoyer then tried to make the argument that all teams change and referenced the Red Sox teams who he characterized as “completely different” over their multiple World Series wins.

With all due respect to Jed Hoyer, I wish there had been one more follow-up question here. Those Red Sox teams that won were not “completely different.” David Ortiz was on three of those teams across 13 seasons, Dustin Pedroia was on two, and played all of his 13 seasons in Boston. I understand that Jon Lester eventually changed teams, and also, that was arguably a mistake on Boston’s part. I was in the city to read the articles bemoaning the team’s decision to trade him to Oakland while hoping he’d magically return to Boston some day — only to lose him to their own previous front office members in Chicago in 2015.

As the questions moved to current Cubs players I was impressed as Jed talked about the importance of team leaders and the development of those skills he sees in Nico Hoerner and Happ — but it was impossible not to juxtapose that with the fact that Ian Happ is in his final year of team control and, notably not extended. While the panel continued to some issues like MLB blackout restrictions and Joe Maddon’s recent book, I wondered if a year from now some young fan would ask Hoyer the same questions about Happ that were asked about Contreras and Rizzo today.

This was the most candid conversation I’ve heard with Hoyer and Hawkins, and I was grateful for that. As I mentioned in my writeup of the Ricketts family panel earlier today, there are a lot of teams who have canceled their fan festivals rather than take tough questions. To the Cubs’ credit, they had those conversations. But at some point this front office will need to take an honest look at a free agent market that is clearly too rich for what they consider to be intelligent spending and grapple with what it means to be a fan. Rizzo, Contreras, Javy, KB and Schwarber are not widgets to fans on the North Side of Chicago. We are Cubs fans because we want the opportunity to cheer for our favorite players for life and then build statues to them decades later. It doesn’t seem that Hoyer or Hawkins understand the latter part of that equation at all.