One of the best parts of Cubs Convention is the access fans have to the organization’s biggest figures. Whether in passing in the convention’s hotel lobby or during hour-long panels, fans have opportunities to meet members of the Cubs and ask legitimate questions on the state of the team.

An example occurred Saturday, when a fan had his two minutes of fame during the baseball operations panel.

“The fact that it has been a slower offseason and the fact that it’s pretty obvious we don’t want to increase payroll,” the fan said to team president Theo Epstein and general manager Jed Hoyer. “I know we have a high payroll already, so it’s not like the money hasn’t been spent. Has the slow offseason, [has] it just been attributable to the luxury tax, or are there more factors in play, or at least factors that you can talk about?"

For the second straight year, the Cubs arrived at their fan festival having made little moves to upgrade a roster that ended the previous season on a disappointing note. As the fan said, MLB’s luxury tax threshold clearly is an issue. If the Cubs exceed the threshold ($208 million) again, they’ll be taxed 30 percent on their overages and see their 2021 draft pick drop 10 spots, should they eclipse the threshold by $40 million.

For a team that hasn’t had the most success in the draft in recent years, all while not winning in or even making the postseason — despite holding one of MLB’s biggest payrolls (projected just over $209 million in 2020) — those potential penalties are enough to give pause.

“Your question, the way you asked it, is perfect,” Epstein said to the fan. “It outlines the challenges we have. Transparency is very, very important to us. We do the best we can to always tell the truth and always be as open and candid as we can. We think you guys deserve that.”

The Cubs have been knocked in recent years for a lack of transparency. That matters, but there are some areas where they won’t show their hand. Budgets and player payrolls are examples, as revealing too much would hurt them when negotiating deals with agents and opposing clubs.

“But obviously I’m not going to insult you guys,” Epstein added. “Clearly, how we’ve positioned 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. It’s one of those obstacles that we’ve talked about that we have to find a way to navigate around.”

Fans frustrated by the Cubs sitting idly this offseason and last are quick to point out the luxury tax is merely a de facto salary cap. The financial consequences aren’t overbearing — the Cubs paid $7.6 million in overages in 2019, a small cost for a big market team.

The Cubs aren’t rebuilding and intend to compete in 2020, but their farm system has grown barren from years of win-now moves and struggling to develop impactful homegrown talent. And, on top of all that, many of their core players — Javier Báez, Kris Bryant, Anthony Rizzo and Kyle Schwarber — are projected to hit free agency after 2021.

Add that all up, and the Cubs find themselves in a purgatory of sorts as spring training nears.

“I’m going to 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,” Epstein said. “We would have a little bit more flexibility. Any outside factor, like how you position yourself relative to the tax or budgets, is important, but there’s always a way to anticipate that and do your jobs in such a manner that you can get around it.”

Between the desire to compete in 2020, remain competitive long-term and gain financial flexibility, members of the Cubs core have been fixtures of trade rumors all offseason. Dealing Bryant, for example, would give the Cubs payroll relief ($18.6 million salary in 2020) and net the team young, controllable players/prospects. It also would cost the Cubs one of their best players.

At his end-of-season press conference in 2018, Epstein threatened roster changes could occur, though the Cubs largely brought back the same group for 2019. After the club underperformed, winning 84 games, he again hinted changes could be coming.

The Cubs have overhauled their baseball operations up-and-down the organization, but it’s beginning to look like status quo will reign king once again. Bryant’s unresolved grievance case is a factor here, but the club ultimately is struggling to make the right moves to help the team now and moving forward.

“Right now, we’ve been struggling to find the types of transactions that can thread that needle, that can make us better in 2020 and improve our chances of winning the World Series in 2020,” Epstein said, “that at the same time position us so that we don’t run the risk of falling off a cliff after 2021, when a lot of our best players are scheduled to leave and also can get us where we should be relative to the CBT and relative to budgets to ensure a little bit healthier financial picture going forward in the future.

“It’s difficult, it’s not impossible. Probably most of the moves we’re going to make are not going to be able to serve all three of those masters. You might see a move that makes us a lot healthier for the long-term future, which is important to us and we should be doing those types of things, but might create a little more risk for 2020, where you might see a move that…a move that makes us better for 2020, and that’s important.

“We really need to try to improve and take risk away from the roster, but that’s gonna hurt us a little bit down the line after 2021. This is one of those winters where it’s really hard to thread the needle and 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, we’ve done some things that maybe don’t improve the ’20 team but ensure a better future and then to our bosses and for our future, we’ve also done a responsible job financially to set us up for long-term fiscal health.”

With Opening Day nine weeks away, there's still time for the Cubs to make a significant move to their roster. Making one that checks all three of Epstein's boxes, however, is a much greater — potentially impossible — task.