Year-in and year-out, one of the most entertaining parts of Cubs Convention is the fan questions.
Whether posed by children to Anthony Rizzo and his teammates at the Kids Only Presser or hard-hitting questions to Theo Epstein and the coaching staff, fans never cease to entertain when they get their opportunity on the mic.
That continued Saturday morning when a fan got up to ask Epstein a question halfway through his Baseball Operations panel and started innocently by thanking the front office for the 2016 World Series championship. It then delved into the fan stating his belief that the Cubs have regressed in the seasons since, particularly on offense.
"It's been written," the fan continued, "that the definition of insanity is trying to do the same thing over and over again and expecting different results. Yet we're probably gonna have a very similar lineup this year to what we had last year. Can you articulate what we should expect differently and why we should get different results from that?"
The fan was alluding to the "status quo" on the Cubs roster that is becoming more and more of a reality as the start of spring training draws near. To date, the Cubs have not guaranteed a single dollar on a big-league contract in free agency and they also have not traded from their core of players or worked out an extension with anybody from the same group.
The 2019 Cubs won only 84 games and were essentially eliminated from playoffs with a week left in the regular season. It led to sweeping changes on the coaching staff - including the departure of manager Joe Maddon - and every other behind-the-scenes department within the franchise. However, the game is ultimately won and lost on the field by the players and that group has hardly changed apart from the guys the Cubs have lost to free agency (a group led by Cole Hamels and Steve Cishek and potentially Nicholas Castellanos) and via trade (Tony Kemp).
"Great question," Epstein said in response to the fan. "Well, first of all, it's not Opening day yet, so I think there's still a chance of some changes. We hope there will be. This is an offseason where we knew we were gonna be more active in trades than free agency, but the bottom line is: words don't matter, actions do. But the fact that we haven't been active yet makes that a very valid question."
Epstein then launched into a long-winded answer quoting himself on how development isn't linear, and used the up-and-down career Ian Happ has had to date. The Cubs believe there is more in the tank for a guy like Happ, who barely contributed in 2019 while spending the first four months of the season making adjustments in Triple-A Iowa.
Kyle Schwarber was another example Epstein pointed out, referencing the changes the left-handed slugger made that led to a monster second half of the season.
"I agree with you," Epstein went on. "I think, objectively speaking, we should be adding to this team and doing everything we can to make it better. There are some obstacles we're trying to fight through in that regard. But don't give up on the players that have been here that might've driven you insane at times watching them, because I really think a lot of them are on an upward trajectory and will make us proud this year."
About 15 minutes later in the same session Saturday morning, another fan asked Epstein to speak as candidly as he could about the payroll issues facing the Cubs.
The president of baseball operations admitted he is trying to be as transparent as possible, but isn't able to go into exact detail on the payroll because it puts the Cubs in a compromised position as they negotiate with agents in the open market and other teams on the trade front.
At the moment, the Cubs are projected for a roster that will go slightly over the $208 million luxury tax threshold for the second straight season.
"Clearly how we position ourselves relative to the collective bargaining tax and the impact of going over multiple years in a row and the effects of that long term is a factor in the offseason," Epstein said. "It's one of those obstacles that we talked about that we have to find a way to navigate around.
"But I'm gonna be honest and self-critical - if we had done our jobs a lot better the last couple years, those same obstacles might be there, but they wouldn't be as pressing and we'd have a little bit more flexibility."
For example, the Tyler Chatwood contract hasn't really worked out for the Cubs to date. He's owed $13 million in 2020 and while he had a resurgent season last year, that's still a lot of money for a guy who may not even be ticketed for the rotation this summer.
Same with Craig Kimbrel. In early June when the Cubs signed the dynamic closer, it looked like a no-brainer addition to shore up the weakest part of the roster - not only for 2019, but for the next two years after. Now, after a half season that was plagued by injuries and ineffectiveness, Kimbrel is on the books for $16 million in 2020 and yet comes with plenty of question marks.
If the Cubs didn't make those two deals, they'd have two more holes on the pitching staff, but also a lot more financial flexibility to fill those spots. It also speaks to the lack of pitching development under Epstein's regime, which has forced the front office to continually devote a lot of resources into signing pitchers instead of supplementing the staff with homegrown arms.
Couple the money issues with the fact the projected roster has lost a lot of talent from the end of last season and the nearing free agency for the likes of Javy Baez, Kris Bryant and Anthony Rizzo, and Epstein's front office has been left in a spot this winter where they have to "serve three masters," as he put it Saturday.
They're still trying to contend in 2020, but they don't want to put themselves in a further bind financially and they'd ideally add pieces that would help the team both in the short-term and the long-term. That includes patience on the trade market as they wait for another team to come closer to their asking price on Bryant or any of the other available players.
None of it is what the fans want to hear, but it's the reality of the situation the Cubs find themselves in.
"This is one of those winters where it's really hard to thread the needle," Epstein said. "We're doing the best we can. I would say to hang with us and hopefully by the time Opening Day rolls around, we've improved the 2020 team and we've done some things that maybe don't improve the '20 team, but ensures a better future. And then to our bosses and for our future, we've also done a responsible job financially to set ourselves up for long-term fiscal health."
The 2020 Cubs: Insanity, the elephant in the room at Cubs Convention originally appeared on NBC Sports Chicago