Questions I’d Like to Hear Answered at Cubs Convention but Probably Won’t

This weekend, fans will be descending on the Sheraton Grand Chicago for the annual Cubs Convention. It’s a chance for attendees to meet and ask questions of players, executives, and ownership. They can be intense at times, but those answering usually skirt the tougher queries.

In that vein, I would like to propose some questions I want to see asked and answered, yet am pretty sure won’t be. I’m going to divide it into three categories: ownership and front office, coaching staff, and players. And if any of you have additional questions of your own, feel free to add them in the comments.

Ownership and Front Office

Why the sudden budgetary restrictions this offseason? Is this due to financial issues or is it a baseball strategy?

This is the question on most everyone’s mind this winter. The Cubs have indicated they don’t have much room left in the baseball budget, with some reports saying they may not add any more salary without clearing existing contracts. The thing I want to know is why is the Ricketts family having cash flow problems or does Theo Epstein and baseball operations feel this is a sound strategy?

Does the front office really feel internal improvements are enough to get back to the World Series without acquiring an impact player?

Immediately after the season ended Theo Epstein held a press conference during which it appeared he had lost some patience with developing young players. Speculation about Bryce Harper, Manny Machado, and others began to swirl. Subsequent public comments have indicated the opposite, that the Cubs feel a return to health and continued development will be enough. Some clarity on the subject would be nice.

Why is Addison Russell still a member of the Cubs?

This question is the simplest and yet the most important that should be asked this weekend. Russell agreed to a one-year contract below expected value. After his domestic violence suspension and further troubling allegations from the mothers of his children, some hoped he would be released. Ownership and management should explain why they feel Russell should still be on the team.

Coaching Staff

Joe Maddon says he is going to be more hands on this season, what exactly does that mean?

Maddon has said he plans to take a more direct role with the players. Is it a general notion or are there specific areas in which he wants to become more involved? It would be nice to for him to elaborate on that statement.

Theo Epstein has offered veiled criticism of Maddon, who is in the last year of his contract. Does Joe feel there is any tension with the front office entering 2019?

The President of Baseball operations said he felt the club had issues with motivation late in the season and he disagreed with some of Maddon’s on-field decisions. With Maddon only signed through 2019 and talking about the idea that he’ll be a free agent, it’s fair to wonder if things are getting tense at Clark and Addison.

Will the training staff be more willing to insist that injured players get time to recover from their nagging injuries?

Kris Bryant continued to play with a nagging shoulder injury that appeared to sap his power last year. He finally went on the disabled list, then came off briefly and had to go back on. In 2017, Ben Zobrist tried to battle through a wrist injury that made it almost impossible for the switch-hitter to bat from the right side. After nearly a month of struggle, he too went on the DL. Did the training staff agree with these moves, were they overruled from above, will this process change for the upcoming season?


Will you feel let down if the front office makes no substantive effort — all due respect to Daniel Descalso — to improve the team this free agency period?

Of course the company line will be toed by everyone at the actual event, but it would be interesting to see what players thought if they were being truly honest. Perhaps this question could be answered at various local watering holes around the city afterwards?

[For Kris Bryant] How much have you lobbied your best buddy Bryce Harper to sign on the North Side?

It’s the question everyone is dying to hear answered. Bryant and Harper have been photographed together numerous times this winter. Who wouldn’t want to be a fly on the wall to hear what they are discussing? It would also allow our leader Evan Altman to pump out even more precious Harper content on Cubs Insider.

What actions can a teammate take that would lose them support in the clubhouse?

With all the Addison Russell allegations, for which he now accepts grudging responsibility, many teammates are still supporting him or at least are willing to give him a second chance. I’d like to know whether there is something a member of the team can do to lose that support? Some might say I’m being harsh, but domestic violence is a serious problem in America and I feel an explanation for why players are willing to look past it is necessary.

[For Addison Russell] Why should you get another chance? Are you really committed to changing your ways?

Russell is not attending the convention so this can’t be asked, but he’ll have to answer it at some point. What he did was truly awful and he doesn’t really deserve the benefit of the doubt after lying about it for so long. I’m not sure if any answer he gives would be satisfactory, but being open about it and being serious about becoming a better person would at least be a positive step forward.

There are sure to be all manner of softballs and oddballs over the course of the weekend, some of which may even lead to legitimate insight. In the end, Cubs Convention is more about granting ravenous fans a taste of the team at time when baseball is at its nadir. As such, the vibe tends to be a little more subdued and hopeful.

You never know, though, the Cubs’ stagnant offseason and failure to make any impact moves could have some folks sufficiently riled up. We’ll find out soon enough.

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