With the Cubs facing a pivotal winter, we’re tackling the biggest questions facing Jed Hoyer’s front office. Reporters Bruce Levine and Tony Andracki provide their perspective.

First up:

If you were Jed Hoyer, how would you handle the situations with Kris Bryant, Anthony Rizzo and Javy Báez entering their last year of team control?

BRUCE

It’s a very difficult question to answer. Cubs fans want to win in 2021. The organization and Hoyer can’t really come out and say, “Our direction is to win this year if we can, but in reality, we need to try to look toward the future.”

Nobody wants to hear that Bryant or Rizzo or Báez are going to be traded or not be signed. These are iconic heroes that people want to keep hold of if they can. In reality, they’re going to have to move on from most of these guys.

Maybe in the case of Báez, you want to sign him for a long-term deal, but you’re also cognizant of the fact that there’s three good shortstops out in the free agent market right now (Didi Gregorius, Marcus Semien, Andrelton Simmons) and there’s going to be five All-Stars out there after 2021 other than Baez (Francisco Lindor, Carlos Correa, Corey Seager, Trevor Story, Brandon Crawford).

So it’s about figuring out what his market is, what he’s worth to you and what is reasonable to him and his representatives. It’s a very difficult process right now for the Cubs.

TONY

It is such a difficult question. We already got the answer with one of those core players with Kyle Schwarber non-tendered this winter. With both Rizzo and Báez, you see what the market will be. With Rizzo, you’re talking about a 32-year-old first baseman as he approaches free agency next year. He means so much to this franchise both on the field and off.

Both Rizzo and Báez are players the Cubs and fans would want to keep around as long as possible in Chicago.

With Bryant, it’s a lot more difficult. You want to keep him around for sure if you’re trying to contend in 2021, but he’s also somebody the Cubs could trade away in exchange for long-term pieces. I think you go into 2021, see how the season plays out and if you are in contention, hang on to Bryant and get draft pick compensation for him next winter if he does leave. If the Cubs aren’t contending, they could always trade Bryant at the in-season deadline.

Either way, determining the long-term future of these three stars is priority No. 1 for Hoyer and Co. this winter.